Suspicion | The Billionaire Murders: The hunt for the killers of Honey and Barry Sherman - S2 The Billionaire Murders | E11 Gift Bags and Blood Stains Part 2

Episode Date: December 20, 2024

In episode eleven of “The Billionaire Murders: The hunt for the killers of Honey and Barry Sherman” Kevin Donovan uses what he knows about the killings to develop his theory of what the killers were after. Nothing was taken, not money, jewelry, and none of Barry’s electronic devices. The plan was to kill both Honey and Barry and stage their bodies. The Billionaire Murders podcast is probing the strange case of the famous Toronto couple found strangled in their north Toronto home in 2017. For seven years, The Star’s Kevin Donovan has covered the case for the Star, fought court battles to access documents on the police investigation and the Sherman estate, written a best selling book on it and produced a Crave documentary. Listen for episode 12 this coming Friday, December 20. 

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BetMGM operates pursuant to an operating agreement with iGaming Ontario. From the Toronto Star, I'm Kevin Donovan, and this is Billionaire Murders. Episode 11 Gift Bags and Bloodstains Part 2 In the last episode, I began piecing together everything I knew about Barry and Honey Sherman's last day, Wednesday, December 13, 2017. The morning workouts, Honey shopping for Hanukkah gifts, Barry spending the day at his company Apotex, ending with a meeting with Honey and three builders to discuss plans for a new

Sherman mansion. And how one of the builders remembered Barry, a workaholic who normally stays at the office until 11 p.m., said he had to go home early that night for a reason that, unfortunately, none of them could recall. I ended the episode with a stark contrast, Honey being attacked in her kitchen shortly after she arrived home at 8 p.m., and Barry sending a last work email before heading for home early. Agreements with PMS, re-de-joccin and hypertropium. I can't find either. Do you have? Barry's drive home from Apotex in his aging car that night would take no more than 25 minutes.

His top executives Jack Kay and Jeremy Desai, they drove high-end vehicles. But Barry loved his 10-year-old Ford Mustang convertible. He'd recently had an accident on the same highway he took every day to get to work. Here's Jeremy DeSai, who was then the CEO of Apotex. He had a crash on the 400, a minor collision, but pretty well his Mustang, what, silver one, was all dented up.

Now you'd expect a billionaire to just get a new car. In fact, Honey, Barry's wife, recently had an accident in her 10-year-old SUV when she'd hit a deer driving home from a friend's cottage. Honey got her brother-in-law to shop around and find a cheap auto shop. She proudly got major damage fixed for the bargain basement price of $5,000. Same for Barry. So Jack and I said to Barry, we are going to buy you a new car. Jack goes, Jeremy and I are going to buy you a new car. He goes, no way.

He goes, I'm going to go and see how much it got repaired. He spent $2,000 on it. He comes in very proud about three weeks later and he comes out, he goes, look, see, all these panels which were rusted, which had also got dented, had been replaced. That's the car Barry was driving that night. Jeremy recalls a comment Barry made that was, sadly, prophetic. Ironically, he said, in in very prophetic statement, this was in

September, he goes, this will last me until I die now. Okay, back to the timeline. Barry has left the office around 8.30 p.m. His route takes him south on a major highway called the 400, then east on another major highway, the 401. Then he take the Bayview Avenue exit and it's a short hopped old colony road. He arrives home just before 9pm. I've talked to a lot of people who knew Barry Sherman well and one of the questions I have asked relates to his parking underground. Some say he never did, others say half the time he parked out front of the house in the half-circle driveway and sometimes he parked underground

This night I think the same person who got Barry to go home early Also suggested he park underground Using a ruse I've not yet figured out But when you think about it, it makes sense for the killers to want Barry to park underground He wasn't a little guy, he was tall and overweight, so he'd probably weigh close to 200 pounds. Getting Barry down the staircase to the basement wouldn't be easy, so that night he drove his Mustang down the ramp. Using the crime scene photos police took when they first entered the house, I'm going to

reconstruct to the best of my ability what happened next. Let's start with the garage. It's a big space. It would hold 10 small cars jammed in. The photos show just Barry's Mustang. Coming down the ramp, it appears he made a left and pulled in beside the door that leads into the basement hallway.

There's very little else in the garage. To the right of his car are a bunch of cardboard boxes. Some have sparkling water bottles, some have wine. To the left of his car, I can see some half-filled black garbage bags, two of them. In front of the car and to the left of his car, I can see some half-filled black garbage bags, two of them. In front of the car and to the left is the double door that leads into the hallway. Barry pulled the car right up to a curved wall of glass block to the right of the door. It's that cubed opaque glass that was popular in early 1980s construction.

On the other side of the glass block is the hallway. I'm assuming the killers were waiting on the other side. They would have seen Barry's headlights through the glass block as he pulled in. Barry gets out of the car. He takes with him three things, his beloved Blackberry, his winter driving gloves, and a home inspection report for

Old Colony that he'd marked up and promised to bring home for agent Elise Stern. That's the bulky document he took off his desk when he left Apotex for the night. The house had been on the market for two weeks. There'd been a few nibbles and one offer. That had been one1 million under asking, and Barry wanted to point out to Elise all the great features of 50-old Colony. I guess it was the micromanager in him. I've interviewed Elise, and she certainly seems to know her job.

Carrying these two things, Barry walks the few feet to the door that leads into the basement hallway. He opens it. One of two things happens. Either the attackers grab Barry as soon as he enters the hallway and he drops his papers, blackberry, and gloves. Or, and this is my theory, the attackers have positioned Honey in the hallway on the floor and Barry, surprised, drops everything. Then they grab him. We can assume that one

of these two things happened because two days later, just before she discovers the bodies in the swimming pool room, Elise Stern, the agent, tours clients along that hallway and finds the papers, his blackberry, and his gloves scattered on the floor outside that garage door. We have a voice actor reading from her recollection of the events. There were papers on the floor and his leather driving gloves. And I remember thinking, like, what the hell? I'm trying to sell a house here. Not realizing that she's disturbing evidence in a homicide, Elise tidies up and continues

the tour. I picked them up and I put them on the side and I put the gloves on top of it, like on a ledge, which is pretty horrible, but who knew? The way everything was scattered indicated something had happened suddenly. That they were left behind showed me the killers had no interest in anything other than killing the Shermans. One can only imagine the corporate secrets that could be accessed through Barry's Blackberry. The killers didn't care.

Just like they didn't care about the $7,500 in Honey's purse upstairs or her phone. I think this is all evidence that the only thing they wanted was both Shermans dead. Once the attackers had Barry, they bind his wrists just like honey's were bound. So how do I know that? Do you remember I told you he had taken sections from the wrists? That's retired coroner Dr. Jim Carons. He was hired by the Sherman family to arrange a second set of autopsies.

The day the bodies were discovered, the Sherman family had heard police were pursuing a murder-suicide theory and they wanted a second opinion. Dr. Karens brought in Dr. David Chason, a veteran pathologist, much more experienced than the one the police used. The first autopsies were done the day after the bodies were discovered. The second autopsies were done four days later, the day before the Sherman funeral. Dr. Karens told me that when Dr. Chason did his autopsies, he examined samples or sections of the skin from the wrists of the Shermans. He discovered a certain type of cell damage that only occurs when a tight binding is applied while a person is alive.

With blood still pumping, the flow would be constricted by the ligature, causing this specific type of cell damage. We don't know how long the Shermans were bound while alive, but they were bound. And then the fact that they had ligatures around their wrists. The forensic evidence that the wrists were tied, and to be clear, there were no ties found at the scene, is one of the findings that convinced this veteran pathologist and the veteran coroner that this was a double murder. To this day, Cairns is disgusted with how the case was initially handled by Toronto Homicide and the coroner's office.

But you know, Kevin, Toronto, please stop this up, go ahead. Okay, back to the crime. We know Honey came home at 8pm and was attacked. Barry is home around 8 p.m. and was attacked. Barry is home around 9 p.m. From his phone logs, we know Barry received a call on his Blackberry at 9.01 p.m. It came from lawyer Douglas Hendler, who was calling Barry about a pressing issue with a mortgage. Hendler's call went straight to voicemail, and Barry didn't reply. I asked Apotec CEO Jeremy Desai about Barry's telephone and email habits.

He was prompt like anything. I mean, if you wrote an email at midnight, one minute past midnight, you get a response back. Given that Barry was so prompt, and I'm told rarely let a call go to voicemail, let's assume that by 9.01 p.m. when lawyer Douglas Handler called, the attackers already had Barry. He's tied at the wrists, using the same type of zip tie that was used

on Honey. Now, there's all sorts of theories about what happens next. Do the killers try and extort money from Barry? Do they use Honey still alive at this point as a bargaining chip? Or once they have them both, do they simply kill them? I've heard all the theories. My answer is, I don't know. The fact that they were bound at the wrist suggests some sort of conversation took place between the attackers and the Shermans, and only the killers know what was said.

What I do know is at some point, both are strangled to death. Not by the belts that were found around their necks. Those were just used to pose them. The autopsy results indicate they were both garroted with a thin cord or tie, quite possibly one of those large zip ties I mentioned earlier, the kind used to bind cables.

That theory comes from a mark found on Honey's neck. Four tiny markings, sort of like dimples, arranged in a square pattern. It's similar to what can be found on the end of one of those cable ties. And to be clear, no ties of any kind were found at the scene. These ligature marks from the plastic ties used to kill them were underneath the belts, which were later looped around their necks. The first pathologist failed to correctly identify those marks. We'll be right back.

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gambling or someone close to you, please contact Connects Ontario at 1-866-531-2600 to speak to an advisor, free of charge. BetMGM operates pursuant to an operating agreement with iGaming Ontario. Once dead, the killers take both of them down the long hallway to the swimming pool room. To get into the room, the killers would have to press a shoulder-height security button just outside the door, a protection against young children getting into the pool room. There's an old video camera in the swimming pool room, but it hasn't been hooked up for well over a decade. It was a monitor that could be used to watch children in

the pool from upstairs. Not exactly the best lifeguarding technique, obviously. Now, I mentioned I have the crime scene photos of Barry and Honey as they were found. They're not for the faint of heart, but there's important clues in them. So I want to spend a bit of time going over what they reveal. First, the pool itself. It's a lap pool, a long rectangle, 15 by 45 feet, running horizontally along the back of the house in the basement. The rarely used pool has a blue pool cover floating on top.

On the left side of the pool is a tiled deck that runs the length of the pool. Looking closely at the crime scene photos I can see what appears to be a faint drag mark leading up to where Honey is positioned. Investigators theorize that Barry was carried by two people but possibly just one of the attackers dragged Honey with the soles of her shoe or heel making that drag mark. On the right side of the pool, the pool waters go right up to a row of dark stone tiles, and above them is a glass block wall that runs the length of the room.

It abuts the hallway, the hallway Barry entered from the underground garage. From the door that enters into the pool, it's about 55 feet to where Barry and Honey's bodies were positioned. Staged, that might be the more correct word. The bodies are at the end of the pool, on the other side of steps that lead into the water. They are side by side. Barry is on Honey's far side, closest to the back wall. If Honey was taken there first and put in place, Barry would have had to be lifted over her.

As to their placement, there's a three-foot-high metal safety railing that goes around this end of the pool. The Sherman's bodies were positioned underneath this railing. Belts have been looped around their necks and tied to this low railing. If the belts were not holding them up, both Shermans would have fallen backwards into the pool. Here's how the lead detective at the time, Detective Sergeant Susan Gomes, described their positioning. Detective Sergeant Susan Gomes, Chief of Staff, Shermans' Detectives' Office, Shermans'

Department of Health, Shermans' Department of Health, Shermans' Department of Health and the Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department of Health, Shermans' Department Honey and Barry Sherman were found deceased in the lower level pool area, hanging by belts from a poolside railing in a semi-seated position on the pool deck. They were wearing their clothing. Gomes used the word semi-seated, but it's not quite accurate. There's a link in the show notes to a sketch a Toronto star artist prepared

based on the crime scene photos. The Sherman's backsides are on the pool deck. Their legs are stretched out in front. Both are reclined back the waist, more than a 45 degree angle. Their arms are at their sides. Honey's head is not much more than a foot above the pool deck. Barry's back is against a railing support. He's a bit more upright. Brian Greenspan, who was the Sherman family lawyer for a time, saw the photos and described them like this. Sitting next to each other with ligatures pulled up around their necks

and wrapped around a railing, forcing them into an upright position. Barry Sherman's legs were outstretched, with one crossed over the other in a passive manner, wearing his undisturbed eyeglasses and his jacket pulled slightly behind his back, which would have prevented use of his arms. I've studied these photos closely. Greenspan is mostly right. But I don't think the bomber-style jacket Barry is wearing is pulled back to prevent use of his arms. I think it's just bunched up because of the way he's positioned. His white shirt tails, which Barry always tucked in neatly when in public, are loose, probably pulled out of his pants in the struggle. Greenspan's comment about Barry's eyeglasses

and his crossed feet is astute though. If, as was originally assumed, Barry had hanged himself, he wouldn't look like that. Strangulation is a violent act. The body contorts, arms and legs thrash. This is clearly someone who was positioned after death. And Honey's shoes, which are open-backed camels, are still on her feet.

I think the killers put them back on after she was positioned, as they surely would have come off in the earlier struggle. Lawyer Greenspan said the autopsies their more experienced pathologist did closed the door on the murder-suicide theory. The conclusion of Dr. Chaston's post-mortem examination of Berry and Honey Sherman, it became clear that they were both murdered. And the Toronto Police Service

should not have drawn any conclusion which suggested self-inflicted injury. What else can we learn from the crime scene? There's no injury to Barry's face, but Honey's face, mainly the right side, is covered in dried blood from that blow to the face when she was attacked. The blood covers her right ear, too. As I mentioned, and this is the theory of some of the

investigators, it appears that a plastic bag was placed over Honey's head. The dried blood is mottled. It looks like plastic was placed against it, then taken away. There's also blood in two other places on the Shermans. There's blood on the blue jacket Honey is wearing, near her right elbow, which is resting on the pool deck. This appears to come from blood on that spot of the pool deck. This blood may have come from her face, given its location just below her head. There's also blood on Barry's right pant leg, near the ankle.

Investigators theorize that one of the killers had blood on his hand when he moved Barry into place. Finally, there's a bloody smudge on the railing close to where the belt around Honey's neck is tied. Police have said they learned nothing forensically from their review of the crime scene. So I'm assuming these blood stains and smudge all came from Honey.

Police have presumably tested them, but the results remain under seal. Now the belts. In both cases, the strap is slipped through the buckle, this is looped around their necks and tightened. Then the strap end is tied around the low railing above. But the belts are tied in a different way. Barry's belt, a plain black belt, is looped only one time around the railing and tied.

But the belt around Honey's neck is wrapped three times around the railing. Also, the direction the belts are tied is opposite. Investigators have theorized that one was tied by a right-handed person, the other by a left-handed person. As to the belt around Honey's neck, it's a much longer belt than the one around Barry's neck. And unlike Barry's plain black belt, there's a pattern in the leather on the belt used

for Honey. I can best describe it as a snake skin pattern. Hopefully police have done a deep analysis on this. I say hopefully because the police missed a lot of things when they processed the crime scene. Here's Detective Sergeant Gomes from that press conference six weeks into the case, the one she gave after my story on the second autopsies caused them to announce it was, in fact, a double murder.

We'll be right back. At OLG, we get to meet winners from across Ontario every single day. We celebrate many of them and their amazing stories and unique dreams. Because every lottery winner has one thing in common. They played. There is only one secret to winning, and that is to play. If you play, you could win. And then, we may get to meet you too. Play in store or at olg.ca and bring home the win.

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Detective Sergeant Gomes used the words forced entry. I found that less than transparent. The Shermans were well known for not locking their doors. The fact that a door was not jimmied open is not as relevant as she makes it out to be. Let me tell you two things about the doors to the Sherman home. First, a side door leading out from the basement to a patio was unlocked when Realtor Elise Stern arrived on the Friday morning, just before she discovered the bodies. Stern has a habit of checking locks and doors as she does a tour.

I don't know if the police learned that from questioning Stern, but I did. More importantly, the Sherman's private investigation team, who are all retired Toronto homicide detectives, discovered that the front door lock was broken. The tumbler's inside didn't function. Any of you listening could have opened that door using most keys or even a screwdriver. The police missed that in their six-week investigation. Investigators couldn't determine when this was done. It may have been broken years ago, and anyone with regular access to the home would know this. All of the mistakes made by the Toronto Homicide Squad caused Sherman Lawyer Greenspan to say

this one year into the investigation. The police failed to properly examine and assess the crime scene where Barry and Honey Sherman were located in the basement of the school. They fail to recognize the suspicious and staged manner in which their bodies were situated. Police are required by law to maintain a certain professional standard in their approach to investigation. But in this case, at this stage of the investigation, the manner in which the Toronto Police Service conducted itself, though well below that standard, as our reasonable officer in similar circumstances should have acted. We know more about what happened inside the Sherman home now, but there are still so many

unanswered questions. Toronto police have said the motive was financial and they believe the targets were both berry and honey. But who died first? Forensically, it's not possible to answer that question. That's because the killings were likely 30 minutes apart. Then the bodies were not found for 36 hours. During that time, they sat in a warm, humid swimming pool room. 36 hours is simply too long to make a proper determination when the killings happened so

close together in time. As to how many killers, here is what I think. Two inside the house, with a lookout outside. I think the lookout was the now infamous walking man that police discovered on home security cameras near the Sherman House that night, caught on video coming close to the Sherman House, disappearing in an area where there's no video coverage,

and then reappearing later in the evening, leaving in the same direction he came from. Through our investigation, we have been unable to determine what this individual's purpose was in the neighborhood. That's Detective Sergeant Brandon Price, now the lead detective on the Sherman case. He gave this update four years into the case, four years after they discovered the video images

he very belatedly revealed to the public. The timing of this individual's appearance After they discovered the video images, he very belatedly revealed to the public. The timing of this individual's appearance is in line with when we believe the murders took place. Based on this evidence, we're classifying this individual as a suspect. Police say this so-called walking man is between 5'6 and 5'9, appears to walk with an unusual gait, bringing his right foot up a bit higher than a normal stride. Doctors who watch the video, which is now on YouTube,

say the individual has a neurological condition called drop foot. To this day, the police, who waited four years to ask for the public's help in identifying this man, haven't a clue to his identity. For my money, this man is a lookout, not the killer. So, who were the actual killers? My theory is there were two of them, and that they arrived at the Sherman property through the backyard, after coming through the yard of a house directly north of the Sherman's.

I think these killers knew the area very well, and knew there was no video coverage. Once in the Sherman backyard, they entered the house through that unlocked door at the bottom of a patio stairwell that leads into the basement. Maybe they'd been in the house recently and left it unlocked, or maybe they were close enough to the Shermans to have a key. Once inside, the killers waited for Honey and Barry to come home. Now, police have nothing to identify these individuals,

as they left no forensic trace behind. But they do have that grainy video of the walking man, who police have labeled a suspect, and who I think was a lookout. At a press conference, I asked lead detective Brandon Price about the dozens of persons of interest he still has on his list. People police theorize might have been involved in the murders. People he says they have been simply unable to clear. With the throng of press looking on, I asked detective Price if he had compared the video of the walking man to all of those people.

To see if any of them matched up in body style, height, shape of face, I had a hard time getting an answer out of him. So I don't like to say that we've excluded people or included people specifically, so we certainly won't get into that but it's a consideration now the the fact is is that nobody can be 100% excluded because there's always possibility and we'll keep an open mind to that there's more than the one individual who executes the action that may be culpable so we're certainly keeping an open mind to that. I try again. But you have a look at those people that you identified as persons of interest to see if their bodies fell out and walking matches?

Price shakes his head yes. It's a rare break from the stoic detective face he normally puts on. Yes. face he normally puts on. Yes, well, we need to get a lot more than that to be able to move that individual, any individual that we are looking at to a level of a suspect. But this individual is a suspect. For my money, this walking man is not the stocky older man he appears to be in this grainy video. I think he's a younger, slender man who has added a limp and changed his appearance,

knowing there are cameras along the route that he walked that Wednesday night. I think the walking man had two jobs, to give a heads up to the killers when first Honey, then Barry arrived, and to watch for any activity in the neighborhood the killers needed to worry about as they made their escape.

It's unfortunate police have been unable to identify this individual. I think the failure to do so can largely be attributed to waiting four years to enlist the public's help. Detectives say they spent those four years trying to determine if the walking man was communicating to the killers or other accomplices via cell phone, combing through cell tower data for years with nothing to show for it. In one of my court hearings to unseal search warrant documents, I put it to police that it was much more likely the walking man was communicating via a handheld radio.

That type of communication can't be tracked. It turns out, police never thought of that. Next time on The Billionaire Murders. You have been abusive to me for over 40 years. Whenever I've asked you to stop, the response has been you stop. You are also persistently abusive to the kids, which you remain unable to see. And you remain insensitive in how you deal with them. The Billionaire Murders, the hunt for the killers of Honey and Barry Sherman,

is written and narrated by me, Kevin Donovan. It was produced by Sean Pattendon, Raju Mudar, Alexis Green and J.P. Fozo. Additional production from Brian Bradley and Crawford Blair. Sound and music by Sean Pattendon. Look out for my book, The Billionaire Murders, and The Craved Documentary by the same name.