Crime Weekly - S3 Ep112: Jennifer Kesse: Secrets in the Sunshine State (Part 1)
Episode Date: February 17, 2023Orlando, Florida - Home of Mickey Mouse and sunny beach vacations, a city that 60 million people flock to every year whether it’s for the theme parks or just the sun and heat that South Florida is k...nown for. But for the friends and family of 24 year old Jennifer Kesse, this city would become a symbol of all that was wrong and evil in the world. Jennifer was last seen on January 23rd, 2006, she spoke to her family and her boyfriend on the phone that evening and said she was going to bed, she was tired from a trip she had just home from. But the next day, when she didn’t show up for work, her parents traveled to her Orlando condo and found everything normal, as if she had woken up and planned to go to work that day. There was still water in the shower, clothes tossed on an unmade bed, and a wet towel in the laundry room. Days later, Jennifer’s 2004 black Chevy Malibu would be found abandoned a mile down the road, in a not so great part of town, but the car held no clues as to where Jennifer Kesse was either. The one clue that law enforcement was able to retrieve should have cracked the case wide open. It was surveillance video of a person parking Jennifer’s car and walking away from it without even a glance back, and the surveillance clicked a photo of this person every three seconds, and every three seconds this person's face was obscured by a tall wrought iron fence. To this day, Jennifer Kesse has not been found, dead or alive, and the people who love her have fought tirelessly for answers, a fight that included receiving over 16 thousand pages of police records on the investigation, and these pages held more clues which has only fed the fire of this mystery. Try our coffee!! - www.CriminalCoffeeCo.com Become a Patreon member -- > https://www.patreon.com/CrimeWeekly Shop for your Crime Weekly gear here --> https://crimeweeklypodcast.com/shop Youtube: https://www.youtube.com/c/CrimeWeeklyPodcast Website: CrimeWeeklyPodcast.com Instagram: @CrimeWeeklyPod Twitter: @CrimeWeeklyPod Facebook: @CrimeWeeklyPod ADS: Daily Harvest Let Daily Harvest do more so you can do less. Go to dailyharvest.com/crimeweekly to get up to forty dollars off your first box. Prose Prose is the healthy hair regimen with your name all over it. Take your FREE in-depth hair consultation and get 15% off your first order today! Go to Prose.com/crimeweekly. Beis Right now, BÉIS is offering our listeners 15% off your first purchase by visiting BEISTRAVEL.com/CRIMEWEEKLY SimpliSafe Customize the perfect system for your home in just a few minutes at simplisafe.com/crimeweekly. Go today and claim a free indoor security camera plus 20% off your order with Interactive Monitoring.
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Tonal.com. Orlando, Florida, home of Mickey Mouse and sunny beach vacations.
A city that 60 million people flock to each year, whether it's for the theme parks or just the sun and heat that South Florida is known for.
But for the friends and family of 24-year-old Jennifer Kessie,
this city would become a symbol of all that was wrong and evil in the world.
Jennifer was last seen on January 23, 2006.
She spoke to her family and her boyfriend on the phone that evening and said she was going to bed.
She was tired from a trip she had just come home from.
But the next
day, when she didn't show up for work, her parents traveled to her Orlando condo and found everything
normal, as if she'd woken up and planned to go to work that day. There was still water in the shower,
clothes tossed on an unmade bed, and a wet towel in the laundry room. Days later, Jennifer's 2004
black Chevy Malibu would be found abandoned,
a mile down the road, in a not-so-great part of town.
But the car held no clues as to where Jennifer Kessie was.
The one clue that law enforcement was able to retrieve
should have cracked the case wide open.
It was surveillance video of a person parking Jennifer's car
and walking away from it without even a glance back.
And the
surveillance clicked a photo of this person every three seconds. And every three seconds, this
person's face was obscured by a tall, wrought iron fence. To this day, Jennifer Kessie has not been
found dead or alive. And the people who love her have fought tirelessly for answers, a fight that
included receiving over 16,000 pages of police records
on the investigation. And these pages held more clues, which has only fed the fire of this mystery.
Hello, everybody. Welcome back to Crime Weekly. I'm Stephanie Harlow.
And I'm Derek Levasseur.
So today we're jumping into a new case, and this was actually a case that you had brought to my attention, even though it has been highly requested.
I've seen Jennifer Kessie's name in the comment section before, so it has been highly requested.
But you told me that you guys were considering doing it on Breaking Homicide a couple years back.
Yeah, and to be fair, someone did recommend it in Instagram DMs or something like that, and it just popped back up in my brain.
It's a case that I wanted to cover on Crime Weekly for a while because, as you just mentioned, we almost did it on Breaking Homicide.
For one reason or another, we didn't. But yeah, this is a great opportunity to cover a case that I feel like
most people have heard of, but maybe not necessarily looked into because it's not a
super popular case that everyone knows about. So I feel like we could definitely
give some more exposure to it. Spoiler alert, it is unsolved. And so they're still looking for
answers. Jennifer's family is still looking to find out who did this. And this case has a lot
of evidence in it. So who knows, maybe something we say here tonight or in the next couple episodes
will jog someone's memory and maybe give a new lead for investigators to follow up on.
Yeah. When I started getting into the case, I think I texted you and I was like, this is a great case because it's got me, it's got me
hooked. And when it, if you know, it stimulates my brain and when I can really get into it and
when I'm like taking a lot of notes and I'm really just like excited about finding out more,
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Jennifer Kessie was born on May 20th, 1981, in Tampa, Florida.
And she was raised in a very tight knit family that included her parents, Drew and Joyce Kessie, and her younger brother, Logan. Now, Jen and Logan were close friends throughout their childhood because he was only
three years younger than she was, and remembering their relationship, Logan Cassie said, quote,
she was always, you know, a big sister. And I know for a long time I was just the annoying
younger brother, but as we got older, we grew closer just naturally, end quote.
Logan played soccer all throughout high school, and he started hanging
out and becoming friendly with Jennifer's guy friends who also played soccer, and before they
knew it, brother and sister were part of the same friend group. Jennifer was incredibly protective
and supportive of her younger brother. She never missed any of his games, and when she went away
to college, Logan would visit her every weekend. But according to Drew and Joyce Kessie, Jennifer had always been an extremely
nurturing and caring person, a person who loved kids, even from a young age. When she was 11,
Jennifer and her best friend made signs advertising themselves as mother's helpers,
and they went around the neighborhood with these
signs trying to get babysitting work. When Jennifer was about 13, she started helping to care for a
special needs child who had a seizure condition and who used a breathing tube, and she dutifully
cared for this little boy until she was in high school. After graduating from Vivian Gather High
School, Jennifer went on to the University of Central Florida in Orlando,
where she was a member of the Alpha Phi sorority before graduating with honors in 2003,
leaving college with a degree in finance. Jennifer was very kind and nurturing, but she could also be
incredibly direct and straightforward, and it wasn't in her nature to be fake. Her father,
Drew, said,
quote, you could piss her off. She would tell you because we're from New Jersey and that's what we do. She would let you know if she didn't like you, if you did something wrong or if you crossed her.
She wasn't a priss. You always knew where you stood with Jennifer, end quote. And that's really
something that I like about Drew and Joyce, Kessie and Logan even.
They didn't sound, I listened to a podcast where they were interviewed and they didn't
sound like Floridians.
You know, they sounded like East Coasters and there was something that I recognized
and understood about them.
Drew Kessie specifically seems like kind of just like a guy that's going to get things
done.
Drew was always in good standing with his daughter, Jennifer, because Jennifer
had always been a daddy's girl since she was small. She was very close to her father, Drew.
And in her early childhood, in Logan's early childhood, Drew actually was a salesperson. So
he worked a lot from home and he said he really liked that because he was able to, you know,
get them on the bus every morning and help them with their homework at night and really get to see them grow up. And it's something that he valued. And you can tell that Drew is, I think, the most
gung-ho of anybody about bringing Jennifer home, even to this day. It seems like this is something
he's not going to stop until he figures out what happened to her one way or the other.
And there's this interview
with him and Joyce, and it broke my heart because you don't even want to, but you kind of put
yourself in the shoes of these parents when you're listening to them talk almost unconsciously. And
it's terrifying because Drew and Joyce, they said, from the moment Jennifer went missing,
our lives pretty much ended. Our lives became specifically about bringing her home and
finding her. And that's it. So that's all we're here for now. There's really nothing else that
we care about. And that's what happens when you lose a child, you have no closure and you have
no answers as to what happened to that child. Your life becomes specifically focused on finding out
what happened because you can't walk away from it. And they just seem to be in one way broken,
but in another way, almost strengthened. Like their will is solidified. They're not going to
stop. This is what's keeping them going now. So it's very, very sad because they seem to really
have a very close family in general. The Cassie family seemed to be incredibly tight knit. I
didn't just say that for the intro. Sometimes we'd talk about these people and we're like, oh, she came from a
close family. No, the Cassie family seemed very tight. Yeah. And I think this goes with a lot
of families where if you lose a child, essentially you're dead inside. I mean, I can't imagine going
on with life knowing that your child may still be out there somewhere.
And so a part of you dies.
And I think with some people that that despair turns into determination where you're like, OK, I can't change the fact that they're gone, but I can dedicate every moment of the remaining elements of my life to finding them.
And if I die still looking for them, then that's how long it takes.
But I feel like we see it with Daniel Robinson as well, with David. I mean, he's dedicating his life to it as well. And so I don't think it's outside the realm of what most parents would do
in this particular matter. But it is unfortunate because there are cases where we work where the
family aren't, they're not as close and this kind
of unites them where with here, like you mentioned, they were already close. They were already tight
knit family, not a normal dynamic where you see the brother and sister so close like that. Usually
it's the opposite. So to have this happen to any family, nevermind a family that's this tight,
it's hard. It's hard. And as parents, I think we feel for them. You're always empathetic to it
because I say it all the time. I don't know how they do it. I don't know how they move on. I don't know how they function. I don't know how they put their pants on every day because I don't I guess you find that strength when you're put in that situation. But it's even hard to fathom just thinking about it. was even saying, she was like, you know, yeah, do we have times of lightheartedness? Do we have times where we laugh together? She's like, yeah, but we always find ourselves feeling guilty about
that afterwards. Like there's never a moment of pure joy that's unadulterated and not tainted
by this thing that's happened, you know, not only to Jennifer, but to us. And I think that's what
a lot of people forget. You know, Jennifer was taken. We know she was taken. She was taken by somebody. We don't
know what happened to her, but she wasn't the only victim here because now the lives of her father,
her mother, and her brother are forever changed and really forever ruined. Because if you truly
love somebody and you don't know where they went and what happened to them, it is incredibly
difficult to move on with your life and stop thinking about them and stop trying to find them.
And so their lives are not only changed, but in a way, like, you know, changed for the very worst.
Like the very worst thing besides dying yourself that could happen is to lose somebody that you love very much. I definitely suggest that if you guys haven't listened to interviews with Joyce and Drew Kessie or even Logan Kessie, listen to them because they are very communicative about how they're feeling.
And it really strikes a chord with you.
So Jennifer was always very close with her father, Drew.
She was a daddy's girl. He said something like, you know, from the moment she was a kid until, you know, the moment she was taken from his life, he always knew when she called him and said, Daddy, in a certain voice that she went away to college because Joyce felt that at this point, she and Jennifer had more of a friend and like adult
dynamic, which really suited them. And Jennifer's parents were incredibly proud of her, and it's
really not difficult to see why. At just 24 years old, Jennifer Kessie was working as a finance
manager for Central Florida Investment
Timeshare Company in Ocoee, Florida, 12 miles outside of Orlando. And although she was young
and inexperienced, and this was her first job out of college, her superiors quickly saw what
Jennifer had to offer, and she was given three promotions in her first year there. According to
her father, Drew, Jennifer had come into the company and started streamlining their operations,
starting with their mortgage department.
After saving the company a ton of money in the mortgage department,
they moved her to a different department, and she did the same thing there.
When she did the same thing in that department,
it was decided that Jennifer would basically just move from department to department, streamlining everything and saving them money. Now, Central Florida Investments holds
more than 14,000 villas and 22 beautiful resorts and premier travel destinations all through the
United States. And they're a world leader in the timeshare and hospitality industry. That means for
her age, Jen was probably making pretty good money.
She was able to buy her first car by herself. And in November of 2005, she made a huge life decision
and closed on her first home, a $210,000 condominium that she had purchased with her own
money with no financial help from anyone else, not even a co-signer. Now, this had been a
big step for Jennifer, and although she had done it on her own, she of course had enlisted the help
and advice of her family, specifically her parents, who were instrumental in helping her narrow down
a list of potential new homes to just one, the condo that Jennifer eventually purchased,
located in an Orlando, Florida complex called Mosaic at Millennia.
We're going to take a quick break and we'll be right back.
Okay, we're back and we're talking about Jennifer Kessy and her buying her first home for herself, which was a condo in Orlando. And at the time that she purchased
this condo, the complex had actually been transitioning from rented apartments to purchased
condos. And Jennifer was actually the first person to purchase a condominium in this complex.
Of the 447 units in the Mosaic complex, only 250 were occupied at the beginning of 2006,
and there was constant remodeling and contractor work happening around the complex and inside
specific units that were being transformed from apartments to luxury condos. According to the
Mosaic at Millennia website, it is, quote, a luxury condo community in beautiful southwest
Orlando with options to purchase or rent. This guard-gated community offers spectacular amenities,
including a state-of-the-art clubhouse, which includes a resort-style pool, movie theater,
fitness center, business center, and billiards. Mosaic at Millennia offers true carefree living, and with 24-hour security,
residents feel completely at peace. Centrally located near downtown Orlando and theme parks,
the location can't be beat, not to mention a near-endless variety of shopping, dining,
and entertainment options right at your doorstep. Mall at Millennia is just 0.5 miles away, making it a short walk to
major department stores, restaurants, and more. End quote. So Jennifer's parents, Drew and Joyce
Kessie, had encouraged Jen to buy a condo in this particular complex for the obvious reasons.
The website clearly states more than once how safe it was there. But not only that,
they stated how convenient the complex is to everything, with the huge Mall of Millennia
literally right across the street, easy access to highways, amusement parks, and downtown Orlando,
and newly remodeled units that were move-in ready. And to this day, Drew and Joyce Kessie feel an incredible amount of guilt
for steering their daughter in the direction of that specific complex. Like I said, the Kessies
were a very close family, and they talked to each other a lot. That was something that was sort of
like a hallmark of their familial bond and dynamic, talking to each other and telling each other
everything. Well, maybe not everything. Drew Kessie would later remember in a bittersweet kind of way that Jennifer had gotten a shamrock tattoo and she
hadn't told him about it, although she had confided in her mother about the tattoo. But regardless,
whether they were in person together for holidays or vacations, the entire Kessie family loved to
sit around and talk. And Jennifer spoke to someone or more than someone from her family
every single day. Every night after they had both left work, Jennifer and her mother Joyce would
call each other from their cars and talk about their day and what was new in their lives as they
both drove to their respective homes. Something else Jen and her mother Joyce loved to do together
was watch crime shows, specifically Law & Order.
Joyce said that they both really liked Law & Order because they felt it was the most realistic of all the cop shows.
And each episode would give you like solutions or, you know, options for what you could do if you found yourself in similar situations in real life.
Joyce said that she felt the show would teach you what to avoid,
how to avoid it, and how to get out of some sticky and dangerous situations. Now, over Christmas
break, Jen had traveled home for the holidays, and she and her mother went out for a girl's day.
They got manis and pedis, and while they were doing that, they talked about some Law & Order
episodes, and Jen actually discussed how she would behave if she was a victim in some of
these scenarios. Joyce said that Jen had talked about what she would do if she were carjacked.
She knew that she should speed up and crash the car, and that would be her best chance
because Jen was safe and she always wore her seatbelt, but maybe her assailant wouldn't
necessarily be wearing his or her seatbelt. Joyce said that Jen knew if she was
being attacked, she should yell fire because that would bring the most attention from people in the
general area. And if she ever found herself trapped in the trunk of a car, Jen knew that she needed to
find the trunk release or at least try to find it or kick out the headlights or something. Before
having kids, Joyce and Drew Kessie had been the victims of a crime themselves.
They'd been held at gunpoint in their own home,
so they always raised their children with that in mind,
the fact that you could become a victim,
so you have to be really aware of your surroundings and always be prepared.
Joyce Kessie said that Jennifer was, quote,
the safest of her sorority sisters, known as Mother Hen.
She made sure people had their seatbelts on and their doors were locked, end quote.
Jen always carried pepper spray on her keychain.
She checked in with her family every day.
And according to her father, Drew, quote, one of Jen's main things was a safe call.
It wouldn't matter if she was in the Target parking
lot walking into the store. She'd have someone on the phone with her from her car in, end quote.
And one of the big things that Jennifer Kessy always made sure to do was to be on the phone
with someone when there was maintenance or construction workers in her condo unit.
And she would also make sure to position herself close to the door. That way, if something went down, she could escape and there'd be nobody between her and the door to
safety. And Jen actually had workers in her condo unit a lot more than she would have liked because
when she moved into Building 22, Apartment 2226 on the Mosaic of Millennia complex, there was still
work to be done in Jen's unit. And reportedly,
Jen felt a bit uneasy about some of the guys who would come into her condo to do work.
And these guys were also constantly around the complex doing work on other units. And apparently,
these were groups of guys that would drive in together in the morning, but management at the
complex was reportedly
letting some of these workers live in unoccupied units while the work was being done. So it felt
like they were always around night or day. Yeah. So to go back to what you said a little
while ago, as far as the parents feeling some type of guilt about guiding Jennifer in the
direction of moving into this particular complex.
I don't think it needs to be said, and I don't think it's going to make much of a difference
to hear it from us, but you can't put that guilt on yourself because it could be any
complex in any part of the country.
You just never know.
And we stress that all the time here, that it's just something nowhere is completely
safe.
It's not to scare you.
All it takes is one second and a bad person to be present and anything can
happen.
So I hope they know deep down that although they might have guilt about,
you know,
guiding her in that,
that,
that direction,
ultimately that wasn't the deciding factor here.
There's a lot of other things that came into it,
which you started to hit to right here.
We're not saying it's the construction workers.
And I think this is something more that you can weigh in on, but on but I can see how it would be unnerving as a woman and Jennifer was an attractive woman to have all these men around your building and to be honest, I've seen situations where you have some guys in that particular field where they're not the most respectful to women specifically who are walking by in the area.
I live in a complex now and we have a ton of construction going on and it happens.
It happens.
And I'm not saying I personally witnessed it, but I hear things through my windows and stuff, conversations that are happening about specific tenants who are coming in and out of the building.
And it's tough.
So I can't imagine as a young single woman having to kind of live in your home where
you're supposed to be safe, but always kind of be on edge because you have these guys
around 24 seven and they're seeing when you come and go.
And they're also probably noticing that you're alone most of the time, which can be scary.
So not saying that we're
going to find out down the road that it was one of these construction workers, but I could see
just in general, whether they were involved or not, I could see how it would be uncomfortable
for someone to live in that situation long-term. Yeah. So apparently a lot of these guys spoke
Spanish. I mean, it's Florida. This is very, very common.
So some of them were undocumented. Some of them were documented. They spoke Spanish.
But what they didn't know was that Jen also spoke some Spanish and understood Spanish fairly well.
And so, yeah, when she'd be outside, like walking from her car into her condo, she would hear them talking about her and she would
know what they were saying about her. Right. So, so there's, there's an issue. And like, personally,
like, I don't, I don't mind, you know, I, I lived in New York city for a couple of years and
nowhere else than New York city. Do you walk down the road and get constantly like leered at by
construction workers and they'll just shout out at you like all the things that are that they're
thinking in their heads and I don't mind that it's like whatever but if they were in my apartment
complex and had access to my apartment the one place where I'm supposed to like lock in and feel
safe that would be a concern to me because it's like you potentially have like 24 potential stalkers who know where you live.
They don't have to follow you home.
They don't have to, you know, stalk you or get information about you.
They know where you live.
And like you said, they know when she goes to work.
They know when she comes home.
They know when her boyfriend comes over.
They know when she leaves to go to her boyfriend's house.
They know that she's usually there all by herself. And so that is very scary. And I'm glad that she
took these precautions by always being on the phone with somebody when they were in her apartment,
always making sure to be between them and the door, that way they weren't between her and the
door. And these are just precautions that you should always take, you know, not even just as a woman, but anybody when you have strangers in your home and it's a place where, you know,
something could happen and there's no cameras around and nobody to help you, you should always
be safe. What did you think about the fact that Jennifer, Cassie did seem to be like very safety
conscious, you know, like incredibly safety conscious. I think it's great first off, but I also think it proves the point where
no matter how much you prepare, things like this can happen. I will say the phone,
there's a lot of debate about the safe call, right? Have it like being on the phone
when you're walking somewhere or while you're in the Uber or whatever. And I see pros and cons to
it. I feel like it can serve as a distraction where
your senses are, you know, you're listening to the other person and therefore not hearing as
much around you. So I think there's an argument to be made for that. And I do think that if
someone's going to attack you, yes, the person on the other end is immediately made aware of that
and they can listen and call someone right after hanging up the phone
but i don't know if that would necessarily deter everyone at the end of the day if they're willing
to grab you quickly it's what is the person on the phone gonna do so pros and cons i don't know
the person on the phone would call the police you know if they hear you like
correct but you're already gone i mean you're already gone you know, you're going to make a sound. I mean, you're already gone, you know, for the most part, if that, if you, that person's not,
even if they call 911 immediately, they could get you out of it. That's why I'm saying,
I don't think it's a bad practice personally for me. I like to just, like I've said before,
stay off the phone, keep the iPod, you know, keep the iPod headphones out of your ear,
have your full attention on your surroundings and any in that way.
If you're looking around and listening, you can tell pretty quickly with your peripheral
vision if anyone's anywhere close to you at any point.
And if you see someone closing in on you, don't be afraid to run to the nearest public
area or back inside the store or whatever.
I mean, a light jog.
Oh, I forgot my keys. Run back in just in case they're not doing anything. But if you're aware
of everything, you can react more quickly to it. Where if you're on the phone, if you're listening
to the person, there is a potential that now my phone's up to my ear. If you're watching on YouTube,
that right side of your face is kind of blocked. And also you're listening. So that right side,
you know, that ear is kind of being obstructed by what could be coming up on you from
the right side. That's just my school of thought. But I do think different people in this field may
have a difference of opinion. I had one question to ask you about the construction and maybe
we're miss, maybe we're not getting the full story, but normally it's not a common practice to let someone move into a condominium or an apartment before it's completed.
Right.
Unless it might be some minor touch up spots like, you know, spackle or whatever.
But to have these workers in the unit while living there, usually the apartment complex management will say, hey, the apartment will be ready on this date.
That's when you can move in and then you're good. So I wonder why she was allowed to move in there before
construction was complete, unless it was just, like I said, something minor where they had like
a couple spots on the wall, they had the spackle and paint, but it sounds like it was more than
that. So, I mean, I think that a lot of things could have happened. They were the apartment
complex or the condominium complex was kind of transitioning, right?
Yeah.
From the renting to the buying.
Jennifer's the first person to purchase a condo here.
So maybe it was kind of like they wanted to get the deal done, right?
And maybe she also had to be out of where she was living by a certain time.
And you're always going to do like a final
walkthrough, you know, when you buy a house or when you buy an apartment. And there could have
been, you know, it sounded like she had a list. Her father, Drew, called it her punch list. It
sounded like she had a list of things that she maybe had noticed when she moved in or just before
she moved in that need to be fixed. So for instance, right before she disappeared,
she was talking to her father about trim
needing to be painted.
Okay, so minor stuff.
Maybe there was some spots she noticed
when she first saw the apartment,
like, hey, that needs to be cleaned up.
It's a little messy.
Yeah, probably.
And she had said like,
well, they're in the apartment.
She was on the phone with him.
She was like, they're in the apartment,
but like, I have to leave.
I have to go to work, and I don't want to leave them here.
So what am I going to do?
I'm going to be out of town this next week.
And her father said, oh, just have them put the paint that they're using in a little container,
and I'll come up this weekend and paint the trim for you.
And then so she said that to them, and then they said, oh, we can't do that.
And then Drew, Cassie finally was like, whatever, Jen, just get them out of there. It's white paint. I'll go
to the store and buy some. I'll paint it. Like, don't worry. Like just get them out of there.
So it seemed like it was kind of like little things that she wanted to be perfect because
this is her first home and she purchased this condo. It wasn't like this was a rented place.
It was a place that was her home and she owned it. But it did sound like they were in there quite a bit.
So I'm not sure why that would be.
Well, that's why I'm bringing it up.
Because if this was minor stuff like, hey, we just need you to fix that trim.
Are we living in a world where these construction workers, because this attractive woman is finding reasons to procrastinate and take their time and come back multiple occasions in order to maybe see her and
hopefully, oh, she's just waking up. So she's in something, you know, pajamas or something small
that, you know, they can maybe get a look at her throughout their day because they're bored. You
know, I'm not saying that's the case, but it wouldn't be the first time I've heard of something
like this if it was. Absolutely wouldn't be the first time. So that is possible.
That is possible. It did seem like they were kind of in their lot and they were like a constant
part of her life. Yeah. New person there. They're around guys all day. Like you said,
it's the first woman moving into the complex. She's attractive. They're taking advantage of
staying in the air conditioned apartment with the attractive young woman. Wrong on all accounts,
but we got to acknowledge the possibility that that's what was occurring. I agree. I agree. Let's take a quick break and
we'll be right back. Okay, we're back. So Jennifer Kessie had moved into her condo on November 24th,
Thanksgiving Day. And exactly two months later, she vanished as she was leaving
her condo for work. At least that's what we speculate happened. But let's go back a few
days and see what events led to her mysterious disappearance that to this day remains unsolved.
On Wednesday, January 18th, 2006, Jennifer left Orlando and drove about three hours to Fort Lauderdale, where her boyfriend,
Rob Allen, lived. Now, Jennifer and Rob had been dating for about a year, and the entirety of
their relationship had been long distance, with Rob living in Fort Lauderdale and Jen living in
Orlando. Now, Rob was a British expat. He had this cute English accent. He was a few years older than Jen, and they had
met unexpectedly in 2005 when Rob's roommate had to go to Orlando for a trade conference,
and he suggested that Rob go with him. They were both single, so they could get a hotel,
do work stuff during the day, and then hang out at nightlife spots in the evening and try to meet
women. So they were at a bar on their
last night in Orlando when Rob's roommate started talking to a woman who happened to be with a group
of other young women, and Rob began chatting with one of those young women who turned out to be
Jennifer Kessie. They hit it off, exchanged numbers, and began talking over the phone and via text
every day. Rob said he remembered when he first drove from Fort Lauderdale to Orlando to take Jen out on a date,
he thought to himself, you know, this is a long distance to drive just for a date, just for a girl.
But Rob said that his willingness to do this was a testament to Jennifer.
Rob said that Jennifer was obviously very beautiful,
but it wasn't her beauty that struck him as much as her outgoing personality, her ability to draw people in with her smile and
the sound of her laugh. Rob said that Jennifer was magnetic. She was smart and friendly, spontaneous,
and up for any adventure, whether it was trying new food or traveling to a new place.
He said that Jennifer gave him butterflies, and by the time they'd been together for a adventure, whether it was trying new food or traveling to a new place. He said that Jennifer
gave him butterflies, and by the time they'd been together for a year, he was head over heels,
and those close to him could see it. Both Jennifer and Rob had been struggling with the long-distance
nature of their relationship because it was usually Jen who was driving to Fort Lauderdale
to see Rob every weekend, and it was starting to get to her, and she was
complaining about it, so it was, you know, also starting to get to him. Jennifer was driving to
Rob's apartment on this January 18th because they were flying out to St. Croix for a vacation that
they both badly needed. Rob said that both of their schedules were so busy they'd been unable
to see each other over the new year, so this trip, which they were going on with some family friends of Rob's, it was supposed to make up for that.
And for Jennifer, this trip meant a little bit more.
She and Rob had a great relationship, but she didn't feel like it was moving forward.
She thought it might be time to take that next step, which would be, you know, moving in together.
And if Rob wasn't able to do that, Jennifer realized
she might have to walk away from the relationship. Now, it is hard to find out stuff about Rob Allen
besides what I told you, but I did read in I think two articles that he was older than Jennifer
Kessy and he'd been married before. So he was a like gun shy about just jumping into another like serious
relationship. Maybe his marriage hadn't gone so well. Maybe he was just, you know,
trying to wait and make sure before moving in with somebody. They'd really only been dating
for about a year, which I guess objectively or subjectively isn't that long for me to date
somebody, but may have felt like a long time for Jennifer, who was only 24.
And she may have thought like, what's next here? So Rob was kind of holding back and holding out.
And Jennifer was like, well, this trip is going to let me know if he's willing to really commit
to me. Yeah. And I think I remember Rob when we were kind of going over the basic information
that's case for breaking homicide. And obviously you're going to look at all potential suspects.
And unfortunately,
boyfriend's going to be on that list.
It's just the way it is because we know the history of that and how that can
go.
And you want to look into if there were any issues going on between the two
of them.
Was there any speculation about infidelity between one or the other where there might
have been a motive for this?
So he was definitely on the list as far as people who could be involved with this, obviously,
you know, nothing against him.
Sorry, Rob.
It's just the way it is.
So, yeah, I was familiar with the name.
And I remember it was just brief that we looked into it as far as like just the overview.
We obviously would have done more if we went there, but he was definitely someone we planned on looking into more if we had taken the case.
I don't put a lot of stock into like gut instincts, but I did, you know, I, like I said,
this, this case did kind of pique my interest and I, I really went deep and I did a lot of
research and I couldn't find out a lot about Rob and his background and stuff, but
just simply from hearing the way he talks about Jennifer,
even to this day, just a few years ago, he was interviewed and he's married and he has kids and
he still talks about her very like he loved her. So I don't think he's involved at all. And I think
they definitely did clear him. Like I said, he lived in Fort Lauderdale. It's like a three-hour
drive. So he wasn't anywhere near Orlando when it went down. But yeah, that's obviously
the initial place you're going to look, Rob. What people in the victim's lives could be
responsible? Who they have problems with? Was there anything that happened in the previous
weeks that would suggest someone had it out for him? You got to check all those boxes first.
Yeah. And I mean, you might even look at Jennifer
like pushing Rob into a committed relationship
as a potential motive,
not a potential motive to necessarily like kill her,
but a potential trigger that might cause an argument
that might lead to something happening.
And then, you know, he didn't mean for it to happen.
It was a crime of passion.
She's gone.
Now he's got to like cover it up. But once again, Rob, we're going to talk about this, but Rob was actually the last person that Jennifer spoke to, which just kind of adds to the, you know, intrigue of course, explore that path. But according to Jennifer's family, the trip to St. Croix went very well.
Jennifer and Rob really enjoyed each other's company because, remember, they are long distance.
They only see each other every weekend.
And a lot of that is like driving and, you know, stressed out.
And then, you know, you got to leave again and then you miss each other all week.
So it was nice for them to spend like a full like four or five days, almost a full week actually, together every single day.
And they really enjoyed that.
And Rob said that a few of his friends pulled him aside during the trip and they were basically like, you know, what are you doing?
Like it's now or never.
There's no point in like trying to protect yourself from getting hurt.
We can tell you're crazy about her.
We can tell she's crazy about you.
She's great.
Like you should commit. You
know, like, it's time because a girl like this isn't going to wait around forever. And it seemed
like on this trip, Jen and Rob really connected, and the door was sort of opened for discussions
about potentially living together. Now, while she was gone, Jen allowed her younger brother,
Logan, who was 21 at that time, to stay at her condo with a few of his friends.
Logan had actually helped Jen move into her condo the previous November,
and she'd given him a set of keys over Christmas.
Logan said that he wanted to spend the weekend in Orlando with his buddies just for a change of pace
since he lived outside of Tampa.
And Logan arrived in Orlando on Friday, January 20th with three friends, Travis, Marlon,
and Matt. But there's a couple of things you need to know about Travis and Matt. First of all,
Travis was Logan's best friend. It seemed like they'd been best friends for several years. So
Travis also knew Jennifer Kessie. Matt was Logan's friend, but Jennifer Kessie's ex-boyfriend.
Because remember, Logan and Jennifer are just three years apart.
They kind of hung out with the same people.
They had the same friend group.
And it looks like Jennifer probably dated Matt, like maybe when they were in high school
or maybe when she was in college.
But she dated Matt for a little bit.
So he was technically her ex-boyfriend. So the four young men, Logan and
his three friends, they hung out at Jennifer's condo. They went to the complex pool. They went
out and had some drinks at different bars. But when they left Jen's condo on Sunday, they made
sure to leave it in the same condition that they found it. On Sunday, January
21st, 2006, Jennifer and Rob flew from St. Croix into Miami, and a friend drove them from the
airport to Rob's apartment, where Jen had left her car while they were out of town. Jennifer decided
to spend the night at Rob's place, and she drove straight from there to her job the next morning.
She left Rob's place at around 6 a.m. on Monday, January 23rd,
and by 9 a.m. she was arriving at work where she was right back into the swing of things.
At the end of the workday, Jennifer attended a staff meeting,
and then one of her supervisors, John Williams, walked out to the parking lot with her.
They both got into their respective cars and drove home, at which point Jennifer called her parents. Like I said, she always did that when she was in the car driving home from
work. Now, at the time she was talking to her mom and dad, her brother Logan was there as well. And
so he got on the phone too, and he informed his sister that his best friend Travis had left his
brand new work-issued cell phone at Jen's condo. Now, Jen said, okay, that's fair, but I haven't even
been home yet, so I don't even know if it's there. I'll look for the cell phone when I get home,
and if it's there, I'll make arrangements to mail the phone to Travis the next day at work,
because there was a UPS and a FedEx right near her job. Jennifer also called Travis that night
to let him know that she had found his phone, and then she was going to arrange the details of getting it back to him.
Now, that evening, Jennifer talked to her mom, her dad, Logan, Travis.
She also talked to some friends who she told about her trip.
But the last person she spoke to that evening was her boyfriend, Rob Allen.
Yeah, so to go back to what we were talking about too,
when you think about Rob as a potential suspect, clearly just had this amazing vacation,
multiple witnesses there who could have attested to the fact that they had issues or they were
arguing the whole time and there was something going on that they weren't aware of, but there
was clearly some uncomfortability about the trip. Doesn't appear to be the case. You would think at this point that would have came out if that were the case.
So they get back home.
Things are good between her and Rob.
One other thing that you would want to look into with a significant other, especially when you mention things like, oh, Jennifer was always going to visit him.
Did he have something else going on?
Another relationship out there that he didn't want her to be aware of.
That could be a motive.
Well, if he's going on vacations with family members, that's probably not the case.
That's probably not the case.
Not always.
I have seen cases where it is, where they're just a pathological liar and they are, but
normally under most circumstances, they're not going to put themselves out there like
that.
And they're not going to be able to disappear to another country for multiple days without
being exposed.
So those things that you would think about as an investigator, when you're looking
into everybody, uh, is something you would consider. I will also say you have these,
these other individuals in the apartment with Logan, one being a previous boyfriend,
nothing nefarious about it. It's fine, but it's something, especially when it's so close to the incident,
it's obviously going to be looked into and very,
very specifically as far as each individual is concerned.
Now you got to look at their backgrounds.
What have they done in the past?
What are their connections to Jennifer?
Has there ever been any issues between them?
Those are all things you want to look into because Logan might think that he
has a bunch of good buddies as far as he knows, but really he has a wolf in sheep's clothing as a friend.
And as soon as he brings them into his sister's home, they may see pictures of her or something and develop a fascination.
There's a lot of things that can happen during that time frame.
Did this guy, Travis, leave his phone there on purpose?
You know, these are all things you have to think about.
You got to, you got to put,. You got to think outside the box. So
we're not saying anything bad here, but we don't have answers right now. So however this
investigation was conducted, you got to try to think differently. And I would imagine at this
point with how many people have looked at this case, these potential scenarios have all been
examined. Maybe they have. But what I'm thinking of, because I thought the same thing, like,
did Travis leave his phone there on purpose? You know, it's his brand new work issued cell phone.
Seems like something you would grab. It seems like, yeah. But I mean, if he had his personal
phone, maybe he was just used to having one phone and he wasn't used to having two phones.
Good point. They're drinking. You know, he wakes up, he's hung over, he rolls out of bed, he leaves.
So I thought that at first. But then I was also thinking about Matt, the ex-boyfriend. You know,
let's say they dated in high school and they broke it off and it was amicable, but now he's in her
apartment and he's like, oh man, like Jennifer's bought this condo and look, I can smell her,
like I can smell her perfume. And suddenly he's like in love again, in love using
quotations. And now he's like obsessed and he's fixated on her, kind of like you said,
he's fixated on her again. She's the one that got away and he can't stop thinking about her.
So I would want to see like, was he texting her? Did he text her when he's in her apartment? Like,
I'm in your house, try to rekindle something, try to open that door again. I would want to know if there was any contact between Matt and Jennifer, even if she didn't
respond. Because sometimes you get a text from an ex-boyfriend and it's obnoxious and you're like,
I'm going to leave you on read or I'm not even going to open this because I know what it's going
to say and I know what's going to happen if I do. And so she just maybe ignored it, but I'd want to
see if he had reached out. And I can't find that information anywhere.
Yeah.
And I think something would have came out by now.
Something would have leaked.
But just from pulling back the curtain as an investigator, regardless of how unlikely
it may be, these are avenues they would have to explore.
You have men, women, doesn't matter, in the victim's home within a reasonable amount
of time of her disappearance.
They're going to be,
I'm sure they were interviewed multiple times extensively.
The Kessie family doesn't really like the way the Orlando Police Department handled this case,
and they're not really happy with the investigation in general. And we're going to talk
about that. But, you know, it's possible that maybe the police, you know, let some things
fall through the cracks. It wouldn't be the first time we've
seen that happen. It's true. It's true. So we're going to take a quick break and we'll be right back.
Okay, we're back. So Jennifer called her boyfriend Rob around 9.57 p.m. and reportedly she made this
call from her landline because cell phone reception in her condo was pretty bad everywhere besides the balcony.
Rob said that Jennifer was tired from vacation and from her day at work, and she was laying in bed when she was talking to him.
Rob said that since he had known Jennifer, they would always talk periodically throughout every day, and Jennifer would always call him on her way to work and before she went to bed at
night. He said that night they spoke briefly. They talked about how hard it was coming back
from vacation, reentering the real world, and going back to not seeing each other every day.
Rob said that they did have a small disagreement that night, but nothing out of the ordinary.
Because they'd just gotten back from vacation, Rob was busy that day and he assumed that Jen would be busy as well. And so he hadn't been as talkative throughout the day.
So he felt Jen needed some reassurance that he missed her as much as she missed him. And, you
know, their separation after being joined at the hip for the past several days, it was as hard for
him as it was for her. She needed reassurance of that. She needed to hear like, you know, he was having as hard of a time as she was with it after
vacation. You know, it's always hard when you come back from vacation and you have to
go back to the real world. Why can't you give me reassurance throughout the day when you are
not answering my texts and I ask you, what are your theories? And you completely ignore it. And then why can't you just say, oh, Stephanie, it's okay.
I don't know how this just became about me. I'm sitting here getting it. I'm writing notes about
the case. And as I'm writing the notes, I'm realizing that you're talking about me and I'm
being attacked. You look super confused. I was. I was like, wait, why is she yelling at Rob? And
then I realized you're
complaining about me story of our life i will agree with you that there's that fall from grace
like you know you're that high you're on this great trip and everything's easy because you're
in this beautiful country and swimming all day no responsibility and then you get home
and it's back to all the insecurities and things you're having issues with that come back to the surface. But I will say it's important that she used her landline for obvious reasons. There could be a situation. I talked about Rob. Well, what if Jennifer was seeing someone else? What if she's calling Rob to say goodnight, but she's not even home? She's with someone else and she's just making a quick phone call on her cell phone. The fact that she's using her landline doesn't completely rule out the fact that there's someone else there, but does decrease
the possibility slightly because why would you be calling another man while someone's with her?
So that's important to note that she did use the landline, which was because of bad cell phone
reception, but it's good for the case. And just to confirm, because we went over a few dates leading up to the vacation, this particular call, this night in question is January 23rd. Am I right? This is the
same day that the Monday, January 23rd goes to work. That night she's on the phone with Rob at
9.57. Correct. Okay, cool. So after Rob and Jennifer said their goodbyes and their good nights,
no one ever heard or saw from Jennifer Kessie again, and we can only speculate as to what happened to her based on the evidence that she left behind.
Now, on the morning of Tuesday, January 24th, Jennifer would normally leave her apartment between 7.30 and 8 a.m. to, you know, walk to her car, get in her car, and drive to work.
And usually, Jennifer would get Rob on the phone as soon as she was in
her car, or at least she would call him and try to get him on the phone. But that morning, she
didn't call him. And Rob said, quote, Jennifer always woke up before me. She had to go to work
before I did. She every day would call me just to say good morning, have a great day, or just text
me to have a great day. Love you. That type of thing.
End quote. So when Jennifer didn't call Rob that Tuesday morning, he did immediately think it was odd, but he was running late for work that morning. So he kind of just left and then he
called her on his way into work and he got her voicemail, which once again was odd, but he left
a voicemail and Rob figured that Jennifer just
had a lot on her plate after being on vacation, and she was probably just busy. Rob tried to
contact Jen again that morning, texting her before walking into a staff meeting, but she didn't
answer, and when he left the staff meeting, he called her again to complain about someone that
he didn't like in the meeting, but Rob got her voicemail again. Rob said, quote, Jen was a great sounding board. She was the first person I'd go to when I
needed advice or just wanted to tell her something interesting or funny, end quote. When Jennifer did
not show up for a morning meeting at her job, the company tried to call her on her cell phone and her
landline several times because it was honestly very unusual for Jennifer to be late. And it was even more unusual for her to just not show up at
all or to be late without calling because she was the kind of person who would call even if she was
running just five minutes behind. By 11 a.m., the CFO of Jennifer's company, Tom, who also happened
to be good friends with Jennifer's parents, Drew and Joyce, he was calling them both, calling Drew and calling Joyce and asking, you know, do you know where Jennifer is?
She hasn't shown up for work and she hasn't called.
Drew Kessie told his friend Tom, don't worry, he would get to the bottom of it. He said his children knew that there was one hard and fast rule, and that was if mom or dad ever call you, you better answer your phone, even if you aren't answering for anyone else.
However, when Drew called his daughter, his call went right to voicemail and so did Joyce's, and that had never happened.
Drew Kessie said, quote, I called and I called.
And for the first time since Jen was a teenager, it went straight to voicemail. In that second, I knew something was wrong, end quote. And his sentiment was shared by his wife and Jen's mom, Joyce, who said,
quote,
And Jen's boyfriend, Rob, said similar things. He said,
quote, it was odd that she hadn't called me back. Something wasn't right, end quote.
So you can really tell that these people are in constant contact with Jennifer throughout the day.
She's very much in communication with more than one of them throughout the day,
to the point where they find it odd
immediately that she's not answering the phone.
For me, it's going to be five, six days before my mom calls the police and says, I'm not
answering my phone because I'm always on do not disturb.
I never answer my phone and I have 257 unread text messages in my phone right now.
So for me, it's like me to not be reachable. But Jennifer was so reachable,
so accessible, and so much in constant communication that all the people who were
closest to her in her life immediately felt like a gut instinct. Something's wrong here.
Yeah, I agree. And obviously, you're used to a certain behavior with someone, specifically Rob
with his girlfriend. Whether he picked up or not, she'd usually call him in the morning and say, hello. That's odd. More so for me
as an investigator, it's just looking at a window, a window that we're looking at that really needs
to be honed in on. And what we have is January 23rd, 10 PM to January 24th at 9 AM. And the
reason I say 9 AM is because that's when she was usually showing up for work based on what you told me about the previous day. So there is a world where she did leave her home
in the morning and she did get out to her car or she was on the road. And I know we're going to
dive into that as far as whether that's possible or not, but just where we are right now, what our
audience knows, it's possible maybe she didn't call him that morning. Maybe she's fine. She gets
in her car and then whatever happens happens. So 9 a is what I'm putting out of it because whether she wanted
to go somewhere else to get coffee and just maybe didn't call Rob that morning, the big thing to
look at is she didn't show up for work. So whatever happened to her had already happened at that
point. So you have basically an 11 hour window, which is not, it's a big window. I mean, when
you're really trying to look at things, but it's not two or three days. And as far as the phone, again,
where we are right now, the questions that you're asking on the surface are, where's the phone?
First and foremost, is it in the apartment? Is it, is it charged? Why is it not? You know,
why is it going right to voicemail? Was it broken? Is the phone missing as well? These are all
questions you're going to want to answer because if the phone is in the apartment,
and I truthfully don't remember if the phone was recovered or not.
So I'm not just like giving hypotheticals.
I do not remember.
But if the phone was recovered and it's in the apartment and it's just dead, well, if
she had charged the phone the night before, it would still have juice.
It would still have some battery life. And secondly, if she had left the apartment unscathed, she would have taken the phone with
her. So there can be some reasonable deduction. You can kind of assume a couple of things
that the phone may suggest if it's still present. Those are some of the things that are rolling
around in my head right now. I want to know more about the phone because the fact that it's going directly to voicemail means that the battery's dead or whoever took Jennifer took the phone as
well and then broke it, shut it off, did something. Because even if they had taken the phone off of
her that morning, more than likely the phone would have been charged. So if they threw it out in the
woods or something, it would still have some type of signal, you would think, unless they were in a remote area, which, again, is also possible.
So I'm going to tell you everything about what was in her apartment, what was not in her apartment and how her apartment looked on the morning that she supposedly disappeared.
And then I do want to see based on that what your idea of what happened is and if it matches up with what the
Kessie family thinks happened. Okay. One more thing. You may not know this, but I wouldn't
put it past you. Do we know how long they were on the phone for that night? Or is it kind of like,
we're just, we know that they got on the phone at 9 57 and we're to assume that it was a relatively
short phone call, which kind of, you know, like most people,
hey, tired, I got work in the morning, just wanted to say goodnight. Or was it a little longer?
Because you did say that they had a little bit of a disagreement on the phone. So it seems like
there would be a little bit, it would be a little bit longer of a conversation. Were they on the
phone for two hours for all we know? Because that would shorten the window again. No, Rob said it was a brief
conversation. And I think it probably was one of the things where it's like they're both tired
and maybe, you know, she's like, I miss you. And he's like, yeah, me too. And he's distracted.
And she's feeling like, you know, I don't feel like you miss me as much as I miss you. And now
I'm feeling like her and my feelings are hurt. And he's like, I'm sorry. I didn't mean to make
you feel that way, blah, blah, blah.
And then they said goodnight and they made up
and got off the phone.
Probably 15 minutes tops in my opinion.
Okay, so let's just go.
And just to be safe, we know they got on the phone at 9.57.
The call probably lasted for longer than three minutes.
So 10 o'clock is a safe time.
10 p.m., January 23rd, 9 a.m., January 24th, because nobody
knows where she is at that point.
So a lot can happen in 11 hours, but we're looking at a new complex.
There's probably cameras in the area.
There's different things that can be checked to try to maybe narrow down that window a
little bit more.
A lot to go off of right here, but I think those two timestamps are very important as
far as what we're going to be honing in on over the series. Absolutely. And I mean, I do want to dive
into exactly what Jen's condo looked like, but let's take our last break really quick and we'll
be right back. Okay, we're back. So a few months before Jennifer Kessie disappeared, her parents, Drew and Joyce Kessie were basically like, we're leaving.
They hopped in the car and they started driving to Orlando and to Jen's condo. But before they
started driving, Drew called his son, Logan, Jennifer's brother, who was at the gym. And he
was like, listen, we don't know where your sister is. She's not answering her phone. Something's
wrong. We're going to Orlando to find her. So Logan also immediately left the gym
and he drove to Orlando separately with his friend Travis. So Logan and Travis actually beat Drew and
Joyce to Mosaic at Millennium. And when his parents got there, they all went into Jennifer's condo
together. Now, previously on the drive down, Drew had called the complex and asked the manager to
check and see if Jennifer's car was parked in her spot. And the manager went to the parking lot and
looked and he came back and said, no, Jennifer's car is not parked there. Next, Drew asked the
manager to go into Jennifer's apartment and check on her. But the manager was like, I can't do that
by myself. Like, I need to have another employee to like enter the apartment was like, I can't do that by myself. I need to have another employee
to enter the apartment with me. I can't go in by myself. So Drew was like, okay, I'll wait.
Go and get someone and then go into her apartment and see what there is to see.
And it took about five to 10 minutes. The apartment manager grabbed another employee.
And then with Drew and Joyce Cassie still on the phone, the apartment
manager and this other employee entered Jen's unit and found everything to be pretty normal.
They said the door had been locked. There was no sign of forced entry, no sign of a struggle,
no sign that anything was missing, and Jennifer was not there. So when Drew, Joyce, Logan,
and Travis entered Jennifer's condo, this is what
they saw. Next to the door in the front hall sat Jennifer's duffel bag, the one she had traveled
to St. Croix with, and that she had evidently sat down on the floor the night before when she'd
gotten home from work. It was still packed from her trip. The condo itself was very neat,
immaculate, basically, the way that Jennifer usually kept it, except for her bedroom and bathroom.
In the bedroom, the bed was unmade, as if Jennifer had slept in it.
And there were some articles of clothing laid out, two skirts and a pair of pants in neutral tones of beige and brown.
And these clothes were laid out on the bed, you know, like, I don't know,
I do that all the time. If I'm trying to pick out an outfit, I'll lay some outfits out on the bed
so I can kind of look at them together. Now hung over her desk chair were the clothes that she had
worn to work the previous day. In the bathroom, the shower still had water on it or in it,
specifically in areas behind bottles of shampoo, and the rounded
corners of those bottles were still wet.
There was a hair dryer and makeup products strewn across the bathroom sink.
There was a t-shirt and a pair of underwear on the bathroom floor near the shower mat,
and a damp towel was found draped over the washer in the laundry room.
The door to the laundry room was
closed. Jennifer's family believes that all of this means that she basically hung up with Rob
the previous night when she went to bed, and she would have had no reason to leave her condo that
evening after getting off the phone with Rob. There was a rumor that takeout containers had
been found in Jennifer's garbage, but Joyce Cassie claims that
isn't true. And Jennifer's refrigerator was stocked with plenty of food. She would have had no reason
to go and get food or order food in after getting off the phone with Rob. And Jennifer was also very
cautious. We've already sort of explored the fact that she was very safety conscious. And even her
boyfriend Rob said that Jennifer would never go out at
night without him. In fact, if she ever had to get gas before making the long drive home to Orlando
from Fort Lauderdale, she would always make sure to fill up her tank with Rob while Rob was still
with her because she didn't even want to risk getting gas early in the morning when it was
still dark out. So she was very safe when it came to that.
Some people have suggested that Jennifer went out after getting off the phone with Rob. You kind of
had touched on that too when you made the statement, well, like, did she call him? If she had called him
from her cell phone, then she could have been out and like with friends or with somebody else. And
she was just calling him to act as if she was going to bed that night.
And it doesn't appear that that was what happened.
However, I will say there were no, you know, video surveillance in the condo complex.
This was 2006.
So there's none of that.
And we wouldn't really know if she went out that night.
She did have a toll thing, her car, so it shows when she goes
through tolls. And on her way home from work the evening before, she went through a toll to get
home. So we at least know her car didn't go through any tolls after getting off the phone
with Rob that night. But I guess it's possible that she could have left. It just doesn't seem
that anyone in her family believes that it's in her nature to do that. that she left on her own under her own free will and you can go off all the shower and stuff like
that which is suggestive more of the morning but it could also be late at night we know it takes a
while for the shower to kind of dry out but the fact that the door was locked doesn't appear to
be any forced entry appears to be that she left under her own under her own power but i will say
to me nothing in the apartment the way it's laid out,
indicates a time at which she left, which could suggest that more than likely if I,
if I was a betting man, I'm saying she left in the morning for work, but it doesn't completely
rule out the possibility that after she gets off the phone call with Rob, she could have already
been getting ready to go out or go somewhere where she's telling him I'm about to go to sleep, but she just got out of the shower. She's already picked out her outfit
and, and had put on her makeup. But again, I'm throwing it out there with a high level of
skepticism because she had to work the next morning, 9am. So it wouldn't make a lot of sense
to go out and do that. And it's not in her behavior. There's no signs that she was doing things like that.
And I'm sure we're going to get into it more, but there would be some form of digital evidence as
well. So whether the phone is recovered or not, I'm sure we're going to get into that.
They would still, law enforcement would still have access to her phone records. So they would
be able to tell if there were, there was activity on her phone or computer after that conversation
with Rob. So I'm throwing it out there as a possibility because I'd be remissed if I didn't tell if there were, there was activity on her phone or computer after that conversation with
Rob. So I'm throwing it out there as a possibility because I'd be remiss if I didn't, but I will
tell you, I don't believe that's going to be the case. You mean that she left then that she left,
I believe that she was in for the night for all the reasons you just laid out. And more than likely
based on what you're saying, that sounds like someone who got up in the morning,
got ready, had a couple of different options for outfits that they put out.
I do it all the time where you'll put out a couple of shirts,
you pick one, you don't feel like folding up the others
or putting them back on the hanger.
So you're like, yeah, I'll get back to that when I get home.
That's what it sounds like to me.
Yeah, so the picture that's painted is,
Jennifer wakes up on the morning of January 24th to get ready for work, as she usually did.
She pulled out some outfit options.
The clothes that were found on the bed were sort of like professional attire.
Which is also important.
Yeah.
It's not like going clubbing attire.
Right.
And they were in like neutral colors, you know, brown and beige. And her family thinks
that she was picking out outfits that would sort of go with the taupe snakeskin heels that she had
just bought and they'd become her favorite. And those heels were actually missing from her closet,
which is why her family believes she wore them to work that day and that she had kind of chosen outfits to go along with that color scheme. And then Jennifer removed the T-shirt and underwear that she'd worn to bed the night before. So that's another kind of sign that, you know, she took the shower in the morning because if she had, if we'd found like her work clothes on the floor of the bathroom, you know, like she had gotten home from work, talked to Rob and then took her work clothes off, put them on the floor of the bathroom, you know, like she had gotten home from work, talked to Rob, and then took her work clothes off, put them on the floor of the bathroom before getting in the
shower. That would maybe suggest she'd gone out at night. But the fact that it's a t-shirt and
underwear, which is, you know, standard pajama, where to bed kind of attire for girls, it does
suggest that she was taking a shower in the morning. And then she gets out of the shower,
she pulls out her makeup and hairdryer.
She's getting ready.
She's getting dressed.
And part of this getting ready and getting dressed
included taking off her glasses and putting in her contacts.
So her contact case was found empty
and her glasses were found in the bathroom,
not on her bedside table
where she would have put them before going to bed.
So this is also very
important. When she was dressed and ready, Jennifer grabbed her stuff, including her work briefcase,
her iPod, her LG cell phone, and Travis's cell phone that he had left there over the weekend.
Remember, she promised she was going to mail it back to him that day from work. Now, none of these
things have ever been found. Not her iPod, not her cell phone, not Travis's cell phone, not her work briefcase. All of this stuff
is still missing. So what does that suggest to you? What is it to just suggest to me that,
you know, somebody didn't want to be tracked, that somebody got rid of those things? Because
even when her car was found a few days later, which we're going to talk about next episode,
when her car is found, those things aren't in her car either.
So it looks like whoever took her got rid of this stuff.
But it also tells me, once again, that she left the apartment of her own.
That's where I'm going with.
And I know we've got more to cover, but that she left with the items she would need for
work, her briefcase.
That's why I'm saying as far as the other scenario that we just discussed, regardless of
where she's going out, whether it's to see another person, whether it's to go hang out with friends,
whether it's to go to a club, she ain't bringing her briefcase, right? She ain't bringing her
briefcase. Or Travis's cell phone. Or Travis's cell phone. Yeah. That's prepared for the morning
because she has things she needs to do. So I think that's with a high degree of certainty,
we can rule out the fact that she had left the apartment the night before. I think it's reasonable to say she left that
morning as expected. I agree, man. OK, but the Orlando Police Department, like for the first
several months, they were like, oh, she probably just like had a fight with her boyfriend and took
off or she probably just went out that night and she's sleeping it off at some
girlfriend's house, even though all the evidence really suggested otherwise. But something I want
to talk about with Travis's phone is I guess it was pinged and they found out that basically the
battery had died over the weekend. So after he'd left it there, most likely even before Jen got
back to her condo, the battery of the cell phone had died. So that was no help.
Yeah. And what's expected, she's not plugging his phone into charge it form,
but I would have expected her phone to have been on for an extended period of time.
Yeah. You would expect it, right? But by the time anybody was trying to call her that morning,
it was already going to voicemail. So by 10, 11 AM., by the time anybody's trying to call her, even earlier, I would say I'm sure Rob tried to call her around like nine thirty, ten in the morning.
It's going to voicemail, which means, you know, somebody's already gotten to it because you would think she'd leave for work in the morning with a fully charged cell phone battery.
Yeah, you would. You would think that, which is, this is leading us to believe that because it was going right to voicemail, whoever her offender or offenders were, they found the phone pretty quickly, it's believed that nothing happened to Jennifer inside of her apartment.
It's believed that she left for work that morning,
closed her condo door behind her, locked it, and walked to her car.
So something happened to Jennifer between her leaving her condo and locking the door
and, you know, getting into her car and driving to work. Many people don't
even believe that Jennifer Kesey made it into her car, or at least they don't believe she made it
into her car alone. And this theory stems, well, a lot of this theory stems from what happened when
they found Jen's car and what was sort of found in and on the car. And a lot of the evidence that was
found on the car wasn't even talked about until like 2019 when the Kessie family had to go to
court and fight for police files. And then they found out that there's a good chance that Jennifer
Kessie's car was the crime scene, which is interesting. And although the
police have claimed that Jennifer could have been abducted the night before after she got off the
phone with Rob, there really is no evidence of that. There's also no evidence that someone entered
Jen's apartment when she was in bed because reportedly she did have a button behind her bed
that if she pushed it, it would alert law enforcement. And that button was
connected and working, but it had never been pushed. So she has all these safety measures
inside of her apartment. And maybe, maybe somebody knew she had those safety measures
inside of her apartment. And that's why they waited for her to come out of the apartment.
Yeah. And I see where you're going with that. Obviously, if you're a family friend, a relative, somebody hanging out with, you know, Logan, you would maybe come upon these things.
If you're a construction worker and you're in the apartment, you'd be aware of these things as well.
And what you said earlier, I know we have to still entertain the idea because police can't say with 100 percent certainty that Jennifer didn't.
She wasn't abducted that night. Obviously, they can't say that with 100 percent certainty that Jennifer didn't, she wasn't abducted that night.
Obviously, they can't say that with 100% certainty because they don't know where she is.
But going back to what we had said, I think law enforcement and we believe that whatever
happened to her happened that morning.
It is, to me, speculative, but highly suggestive that whatever happened to her may have happened
before she
reached her vehicle, right outside the vehicle, or once she got into the vehicle. I would be
willing to bet that in most cases, based on what you've laid out about Jennifer as a person,
that she probably locked her vehicle door at night. So I don't think we have a situation
where the abductor would have been inside the vehicle.
This would have had to have happened outside of it. I just did a project, which you're familiar
with. We won't say it here for, for a network. And we were talking about different cases.
And one of the cases that we covered that there's video on is this guy coming out of an apartment
complex and immediately after like locks his door with his family members,
immediately upon exiting his apartment complex, there's someone there waiting for him to rob
him.
And the guy has a gun.
He holds him at gunpoint.
The guy ends up fighting back and getting shot.
But the point of it is that we could have a couple of things going on here.
If you're a fender, whether it's a robbery or, or for sexual reasons or whatever
it might be, this person has been casing the place for days, maybe weeks. They're aware of
your, of your schedule, of your practices, what you do when you leave, who you're with or who
you're not with when you leave. So they can kind of develop a reasonable degree of understanding
what's going to be the situation when you exit your apartment. And if you're someone who's on your phone, whether it's for, you know, safety reasons,
or just because that's normally what you do, or you're looking down at your phone,
they may have a window of opportunity where they can approach you without you knowing,
or they can approach you and present themselves as someone who's not dangerous.
It could be someone that she's seen before, right? We talk about construction workers.
She's probably recognized a few of them. If one of them approached her as if they were just going
to tell her something about the apartment complex or her specific apartment, she might let her guard
down. So there's multiple situations where she could have been approached and been unsuspecting.
And that's when they could have gotten the jump on her. My personal belief,
just based on what we know about Jennifer, is I don't think she got into the car at any point.
She might've been put in there afterwards, but I don't think she left that lot under her own
free will. I think whatever happened to her happened to her probably before she reached
the vehicle and the suspect was the one who drove the vehicle away. Yeah, I definitely agree that the suspect was the one who drove the vehicle away.
And I don't think that she was in the car, at least not conscious.
I always kind of go back and forth.
Yes.
Like, did they knock her out and throw her in the car?
Or did they grab her, put her in like a nearby waiting van?
Because this is more than one person, maybe.
And then one of the guys
jumps in the car and the other guys drive the van away. A very orchestrated sort of attack.
That's interesting. So why would they, in that case, take the car? If they have a getaway vehicle,
why would they take a car that a bolo could be put out on by law enforcement while they're driving
it? And that gives them a reason to stop that vehicle while they're... What would be the rationale behind taking the car? Well, they didn't drive it,
did they? They drove it a mile down the road and left it in another parking lot. So they just want
it to not be there. That way, if somebody comes looking for her, they're like, oh, she's at work
or she's not here. She's, you know, like at work, like normal. Why would they take her cell phone?
You know, why would they do things like that? This is 2006. It seems like whoever did this was kind of familiar with committing crimes and how
to cover their tracks. In my opinion, this was not a first timer. Professional abduction, you're
saying? I mean, I wouldn't say like professional abduction because a professional abduction to me
sounds like this is a hit, like you were paid to abduct somebody. but it sounds like somebody who's just done it before, you know, for their own benefit, for their own means.
And so they know like how to execute it and they know how to cover their tracks because just your regular average everyday creep who's trying to grab a girl isn't going to be like in 2006, like, oh, let me get rid of her cell phone.
And, you know, most likely the cell phone and
what's his name's cell phone? I forget his name. Travis. Travis's cell phone was probably in her
briefcase. So they probably took the briefcase and just like threw it into like a river or a
body of water or something, you know, to get rid of all the evidence that was inside the briefcase,
including the cell phones. Maybe they didn't even know the cell phone was in there, but they probably got rid of it pretty quickly. Anything
that would kind of like tie to her because they didn't leave anything behind, right? If you're
just going to grab her, why not just like leave her briefcase there, you know, sitting in the
parking lot? Like if you're just going to grab her, throw it in a bush, who cares? They got rid
of it. They don't want anybody to find it. This is more than one
person too, I think. Oh, interesting. Why do you think that? It just feels like if it's, I don't
know. Okay. I don't know. I just, it feels like, because like the car, right? We're going to talk
about the car more. We're going to talk about the car more, but it doesn't look like anybody drove that car a mile away until like a couple hours later, depending on when she was abducted.
And we're going to get into it more, but it seems like this was kind of something that was a team effort, very streamlined, very smooth.
I mean, it's happened in 2006. We're still talking about
it in 2023. We have surveillance footage of this person and we still have no idea who he is. So
it feels very like we kind of, we did this before. We've done this before. Oh, and I forgot to tell
you something about the maintenance workers. So when Logan first got to the apartment complex
and his parents weren't there yet, he was like waiting for them. And he was sort of like walking
around the apartment complex and he was just like knocking on doors. But a lot of these units were
vacant, right? Especially in the area where Jen had lived because they were transitioning those
units into the condos. And there were still people who rented apartments, but they were kind of like on a different part of the complex. So
this part of the complex that Jennifer lived in was kind of isolated because it was the condo
area that were for purchase. And she was the first person who had purchased one. And in fact,
the condo across from hers, directly across from hers, that was getting new carpet put in. So they had
workers in there and they were tearing out carpet and putting new carpet in. So Logan says he gets
there. He's knocking on people's doors. He's asking if anybody's seen Jen, the very few people who
answered. And he said that there was a van, like a big white work van parked in the parking lot.
And there was like a couple of guys sitting in there. And so he went over, like maintenance
worker guys. And he went over and he like knocked on the door.
And he was like, hey, have you seen, you know, a girl?
Like she lives here.
She's in her 20s.
She's usually like got her hair in a ponytail.
Like she lives right over there.
Have you seen her today?
And he said they ignored him.
Like they wouldn't even look at him.
Didn't acknowledge that he was like knocking on their window.
Just looked straight ahead.
Didn't roll the window down. Didn't open it, like literally didn't even acknowledge him.
So then he gets frustrated and he goes around the back of like the apartment building to see if he
can find like somebody who works there and get some answers. And he says he finds another
maintenance worker and he goes up to this guy and he's like, maybe I was a little like stressed out
or maybe seemed aggressive because I was like, hey, have you seen, you know, this girl?
Because he's all stressed.
And he said the guy like freaked out.
And at first he said, no, I haven't seen this girl.
And then when Logan was like, well, are you sure you haven't seen her?
He said the guy like dropped to his knees and he said, I don't speak English.
Like, please, please, I don't speak English.
And kind of like begging him from his knees.
And Logan was like,
that was super weird. And then when he went to go find that person again, he asked the apartment management and they were like, oh, he left. He doesn't work here anymore. So once again,
this is just what Logan Kessie is saying. And we're going to talk more in depth about
the different maintenance workers who were living at the apartment complex and the ones that were
there on the regular. This is just what Logan is saying.
This was a stressful day for him.
So sometimes I think perspective is very important.
He was coming in hot too.
He was coming in hot,
probably scared the shit out of that guy.
I don't know how big Logan is.
I don't know.
Like,
you know,
we don't know what he's,
the guys in the van and I'm not,
I wasn't there.
The guys in the van could be some individuals who don't speak
English and they had this dude coming up to them screaming and they're thinking he's combative
because of something they did. And they might just be like, Hey, don't look at him. He's like
a T-Rex. If you don't look at him, he won't attack. You know, I don't know. I mean, maybe,
I don't know. I think the guys in the van are more suspicious because like, if you're in the van and
you think somebody's yelling
at you and like going crazy at least you'd look at them and be like what you know because you're
safely in your van yeah you know nothing's gonna happen you're two guys against one guy screaming
at you so at least you'd be like what or like look at each other make some acknowledgement
right the guy in the back who was alone i feel like very easily if he did not speak english and
he was undocumented, he might
have thought Logan was from like ICE or from like, you know, some government agency. And so he was
like just freaking out because he doesn't know why this person is yelling at him and why he's like
so aggressive at this point. He doesn't understand what he's saying. So the dudes in the van,
though, they sketch me out. I'll be honest.
I'll be honest. I think at minimum, you look at it where we've talked about it all episode,
these maintenance workers, these contractors, all these people that are out working on this
active complex because it's still being rehabilitated, rehabbed, and you have this
incident occur, which we believe probably occurred in the parking lot near a vehicle.
Nobody sees or hears anything. That's interesting to me.
The one other thing that's running through my head right now,
and we won't ever probably truly know, but it's the why, right?
Why did this happen?
We talk about Jennifer this entire episode.
She was someone who was conscious of her surroundings for the most part.
She was always thinking about these types of scenarios.
If something like this happened to her, how she would react.
She had some self-defense weapons with the pepper spray, things like that. So it looked like she was prepared.
Oh, the pepper spray. The pepper spray was in her apartment on the counter because she had to take
it off her key chain because she was flying and you can't have it on your key chain when you go
through security. So she had taken it off and she had put it in her condo and she didn't put it back
on before she left that morning. This is my point where things can happen to anyone, right?
They can happen to anyone.
But again, she still was in the mindset of like, if someone attacks me, I'm going to
fight back.
I'm going to do something.
So I wonder, and again, was this some type of professional thing where this was an abduction
where they had been casing the joint?
Maybe someone who worked there or someone who had been by had seen her and said she
was alone most of the time. As you mentioned, Rob was-
Like a trafficking situation, maybe?
Like a trafficking situation where Rob wasn't around a lot. As you said earlier, she was,
to the outside, she may look like a young single woman and they tip somebody off and they're
waiting for her because it's pretty brazen to do this in the middle of the morning.
Also could be a situation, which is the situation in the case that I was just referring to.
Broad daylight, young woman dressed nicely, briefcase.
Someone comes up to her gunpoint, wants to rob her, and she fights back, which could have resulted in her being hurt or even killed.
And they decide to take her at that point because now the situation has escalated.
It could be one or the other.
I don't think we'll ever have that answer, but some of it is coming back to me about this case.
And I know there's more information about the car and things that were released later that may have suggest sign of struggle.
So maybe there was some fighting back and maybe this person approached her or people approached her
and told her to basically give something up.
And she said no. And more transpired after that. But this is why this case is so fascinating
because it's relatively new when you really think about it. There's some things that we're
going to discuss in the next part that really drive you are going to drive you guys absolutely
crazy. Because in this case, there's so many small things that if just would have went the other way,
we may not be covering this case right now,
which is really,
really frustrating.
And this is why I wanted to cover it.
But overall,
I think we have a good,
we're up to a good point in this case where we know the backstory.
We know what led up to the day that she disappeared.
And I think we're left with a situation where there's multiple people who had
access to that complex and would have seen her on a daily basis. You have the brother's friends who were in there and would
have kind of seen her security measures, but they're pretty far away. And we already have
Logan and Travis accounted for. There's the ex-boyfriend, I believe you said his name was
Matt. We might not have these answers by the end of this case, but I'm assuming they went and
tracked down his whereabouts for that day. I would hope they did. So allegedly, okay, Matt was at a bar in Orlando pretty close to Jennifer Cassie's apartment or condo that night.
Okay.
But I don't know about the next morning.
Like the night, that Monday night, he was apparently at like a martini bar.
Which could be a complete coincidence, right? And I still think it's the next morning. night, that Monday night, he was apparently at like a martini bar.
Which could be a complete coincidence, right?
And I still think it's the next morning.
All indications are this happened the next morning.
So you're looking at a situation, maintenance workers, contractors, managers, other residents.
I'm sure she was the only one at first, but were there other residents living there at this point?
So there were other people renting because I remember they were transitioning.
So there was other people there like renting.
Right.
She was the first like buyer.
So a lot of potential people who could have seen her alone on multiple occasions,
tipped off someone and decided to try to take advantage of the situation.
And for one reason or another, the assailants decided to take her vehicle for probably the
reason you said it was either a
to transport her a short distance so the suspect vehicle wouldn't be seen at the crime scene
you know take the car dump it at a mile down the road leave the car there and get into the actual
vehicle that may belong to the suspect or his co-conspirators or it's a situation where they're
trying to do one thing. It goes wrong.
Now they have to flee the area quickly in a vehicle.
So they take hers.
It's the closest one there.
Or like you said, it could be a situation where this is premeditated.
This is all planned out.
It's a little bit more of a professional thing.
They purposely take the car to create a longer window where they have a chance to get away
and kind of do whatever they need to do to avoid apprehension.
Yeah.
There's a million things that could have happened, but we know only one thing happened.
And it drives me crazy that we will probably never find out exactly what that was.
Yeah. The why, definitely. I'm hoping, I was so optimistic about this case when we had it,
because there were some things I told you off camera that we were thinking about doing
if we went down there. Some of those things have been done by other investigators,
because a lot of people have thought about going down there and some have actually done it.
A colleague of mine, Jim Rathman has actually talked about doing this as well. I think you
might've met him or I think you, I think you met him before, but there's some potential there that
we could, there could be something done with this down the road. But at minimum, for those of you who don't
know about this case, not only overseas, but also locally, this is a case to be aware of because
we'll have images of Jennifer in here as well. There are some theories out there that she could
still be out there, right? That's something also where people are like, Hey, be on the lookout for
her. So just by seeing her photo, understanding the surroundings,
who knows, maybe someone sees this or hears about it
and can contribute in a positive way.
But we have, what are we thinking?
I know you hate this question,
but two episodes, at least, maybe more,
probably maybe potentially three you were saying, right?
I think three at a minimum.
Yeah.
Yeah. No, it's a good one.
There's a lot to this case.
There's a lot to unpack.
Yeah. There's a lot of meat on the bone for sure. No, I'm looking forward to getting into part two. Yeah. Yeah. No, it's a good one. There's a lot. There's a lot to this case. There's a lot to unpack.
Yeah. There's a lot of meat on the bone for sure.
No, I'm looking forward to getting into part two.
I am too.
But until then, follow us on social media and Derek's going to tell you where.
Still two years later, still doesn't know it.
At drink criminal coffee on Instagram at drink criminal on Twitter.
Our website is not updated yet.
It's criminal.
It's a crimeweeklypod.com.
There's not much there, but we're working on that.
Trust me.
We just did it for criminal coffee co.
Uh, we got new merch coming.
We got all these things coming.
So just give us some time.
We got some things we're working on behind the scenes, but it is coming.
We appreciate all the support with all of that, because if it wasn't for you guys, we
wouldn't be able to do it.
So just bear with us while we get it done.
Cause we want to make sure it's right.
Absolutely. Thank you guys so much. And we will see you next week.
Stay safe. Bye.