Law&Crime Sidebar - ‘If I Die, It Was Greg’: Chilling Texts Just Revealed in Pregnant Teen’s Murder

Episode Date: August 20, 2025

Kylee Monteiro, 18, was last seen in early August at the home of Gregory Groom, the father of her unborn child. When family reported her missing, law enforcement searched the large property in where Groom lived, but found nothing until Groom allegedly drew a map to where he’d buried her body. Law&Crime’s Jesse Weber discusses the very latest with retired detective Will Svilar.PLEASE SUPPORT THE SHOW: If you’re ever injured in an accident, you can check out Morgan & Morgan. You can submit a claim in 8 clicks or less without having to leave your couch. To start your claim, visit: https://forthepeople.com/LCSidebarHOST:Jesse Weber: https://twitter.com/jessecordweberLAW&CRIME SIDEBAR PRODUCTION:YouTube Management - Bobby SzokeVideo Editing - Michael Deininger, Christina O'Shea & Jay CruzScript Writing & Producing - Savannah Williamson & Juliana BattagliaGuest Booking - Alyssa Fisher & Diane KayeSocial Media Management - Vanessa BeinSTAY UP-TO-DATE WITH THE LAW&CRIME NETWORK:Watch Law&Crime Network on YouTubeTV: https://bit.ly/3td2e3yWhere To Watch Law&Crime Network: https://bit.ly/3akxLK5Sign Up For Law&Crime's Daily Newsletter: https://bit.ly/LawandCrimeNewsletterRead Fascinating Articles From Law&Crime Network: https://bit.ly/3td2IqoLAW&CRIME NETWORK SOCIAL MEDIA:Instagram: https://www.instagram.com/lawandcrime/Twitter: https://twitter.com/LawCrimeNetworkFacebook: https://www.facebook.com/lawandcrimeTwitch: https://www.twitch.tv/lawandcrimenetworkTikTok: https://www.tiktok.com/@lawandcrimeSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can binge all episodes of this Law and Crimes series ad-free right now. Join Wondry Plus in the Wondery app, Apple Podcasts, or Spotify. Miss Montero texted a sister that he threw me on the ground and pulled my hair and strangled me. My phone is at 4% and if I die, it was gritty. A grim and shilling turn in the disappearance of 18-year-old Kylie Montero. Her boyfriend, 22-year-old Gregory Riggum. room has been arrested in charge with her murder after police say they made a gruesome discovery on his property. His first court appearance today revealed shocking details that authorities say

led up to her death, and we're going to break it down with insight from a retired detective commander right now. Welcome to Sidebar, presented by Law and Crime. I'm Jesse Weber. Unfortunately, we have a grim update in a case that we've been following here on Sidebar. The disappearance of 18-year-old Kylie Montero. Investigators say that human remains consistent with Kylie's have been recovered. And they were found on the property of her boyfriend, 22-year-old Gregory Groom. We've talked about him before. Groom has been arrested, appeared before a Taunton District Court judge earlier today.

He is facing multiple serious charges. Prosecutors say he also provided details to police about Kylie's death. That's the allegation. We're going to get into those details in a little bit. But this tragic and sad development comes after nearly two weeks of intensive searches across Rehoboth, a small town in Bristol County, Massachusetts, about 50 miles from Boston. Now, the search efforts involved drones, cadaver dogs, dive teams, helicopters. This was all after Kylie was last seen on August 7th at Groom's home on County Street. So I'm going to walk you through her disappearance, what led up to this update.

We go back to August 6th. According to Kylie's family, she reportedly had some sort of altercation with groom at his home. And at the time, there were a few details that were known about the nature of this dispute. But I will tell you, today's arraignment revealed more serious and deeply troubling information. And again, we're going to get to all of that in a little bit. But the incident was serious enough to raise immediate concern among her family. By August 11th, Kylie's sister Kitty Montero made a public plea on Facebook, signaling potential domestic issues in this relationship. In that post, she wrote, there was some domestic issues involved. She is pregnant, and it's highly unlike her to cut all contact from social media and family.

Kylie's other sister, Faith, said she called her after this altercation, telling her she was afraid for her life. Faith offered to pick her up, but Kylie apparently declined. And maybe, most hauntingly, she reportedly sent a message to a friend that read, and this is paraphrased, I don't feel safe right now, something's not right. Well, after that message, Kylie went completely silent. The next day, August 7th, police say it was actually groomed who called to report Kylie missing. August 8th, when her family still hadn't heard from Kylie, that's when alarm bells went off. The teen had been very active on social media. particularly TikTok.

And eerily, her last post was on August 6th, a photo caption in abbreviated form. I don't care what people think about me. For more than a week, Rojobith Police and the Massachusetts State Police conducted tireless searches for her. Again, deploying canine units, drones, dive teams, her family and friends. They took to social media to spread awareness. They shared photos from her prom and graduation. The recent Ataburow High School graduate had just celebrated receiving her deployment. receiving her diploma. She was roughly 11 weeks pregnant, and they also shared details of what was her apparent difficult past.

After her mother passed away, Kylie moved in with her aunt and uncle. She lived there until meeting groom in March when she became pregnant. The couple separated shortly after, but maintained what has been seen reported this on-again, off-again relationship, and Kylie was then apparently living in a shelter for pregnant women. But then authorities returned to groom's home with the search warrant and a backhoe was brought in as crews began digging behind the property. By late in the day, officials confirmed that human remains, consistent with Kylie's, had been discovered. That evening, Rehoboth Police Chief Louis Tabico and investigators addressed the just tragic development at a press conference. Eighteen-year-old Kylie Montero was reported missing by the defendant Gregory Groom on Thursday,

August 7th of this year. The two had been in a dating relationship. She was last reported seen at 107 County Street in Rojoboth, which is the residence of Gregory Groom. It has also learned that Kylie Montero was approximately 11 weeks pregnant. Extensive searches were conducted by various units of the Massachusetts State Police. Based on information obtained during the investigation into Kylie Montero's disappearance, Police obtained a search warrant for the property at 107 County Street in Rojavith that was executed starting this afternoon. As a result of the search of the property, human remains consistent with those of Kylie Montero have been recovered. We await confirmation from the Office of the Chief Medical Examiner.

The defendant was charged earlier today with assault and battery on a pregnant person, intimidation of a witness and domestic assault and battery for an alleged incident that occurred on August 6th. According to court documents, Groom is charged with murder, assault and battery on a pregnant victim, aggravated intimidation of a witness juror, police or court official, and assault and battery on a family or household member. Groom made his first court appearance earlier today where he was arraigned, and we're going to get more into that in a minute, but first to help us get into some key insights into this investigation. I want to bring on a special guest. Will Sveilar, a retired detective commander from the Chicago Police Department.

Will, thank you so much for coming on. This is a really, really sad development. From your experience, what are the challenges for investigators? What do they face when searching for a missing person on private property, especially when you're dealing with human remains being involved? That's a terrible story. It's a terrible story with your updates today. the charges are being announced it's just it's a horrible story when you're looking for a missing

person there are a lot of different factors that are involved in this case it seemed like from the beginning they had a general idea that she may have been with uh with groom uh based on the comment she made or the text she sent to her friends i think they had a general idea of where she was last now where she was currently uh it took him a little while to get to it looks like they brought it out in an interview and the and the drones the cadaver dogs the dive teams the backhose is that typical in an investigation like this how extensive is that it's pretty extensive it's but you're also dealing with a large property I think it was like 25 acres and the property that they were dealing with so if you

have whatever resource you have you use it especially got an 18 year old who's pregnant obviously high risk living in a shelter not the best support system that you could think of, you've got to get everything you can out there. And it sounds like they did. It sounds like they had every resource, you know, state and local, to try to find her. Now, if you've been following us, you know that we have been all on top of this story. And the reason we can do that, the reason we can provide you updates and continue to follow what's happening is because of the amazing support that we get from our sponsor, Morgan and Morgan.

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by clicking the link below or scanning the QR code on screen. Assuming these allegations are true, what are the warning signs that family, friends, what should they pay attention to when a loved one may be in a possibly dangerous, relationship well you know a couple of things they have to pay attention to is one the fact that she became pregnant that is that that's not really a red flag but if you're in a situation where the relationship's not stable or you're two very young people the pregnancy you might want

to take a better look at or keep a better eye on the girl who's pregnant especially when she's 18 years old he's in a relationship with a man who may or may not want the pregnancy and there may probably been mentions some kind of mentioning of domestic violence in the past to her friends so there's a lot of red flags obviously physical condition if you see any kind of bruises or or scrapes you got to pay attention to that but i think the key factor in this one's going to be the pregnancy yeah and i thought that just the social media posts are very interesting right so the lack of social media activity would indicate something was wrong but there was that eerie apparent social media posts from Kylie as well. Does it give you an insight into what may be going on

with someone? Do social media help in that way? You know, they talk so many at times about how you can't really believe anything on social media. People put one image out there. But truth be told, it can really help with investigations, particularly missing persons investigations, right? Oh, massive. It helps massively. And we had a whole unit that was a social media unit that would go into the people's social media, try to find out the history of their posts. If you got something that posts every half an hour or someone that posts at least once a day and then all of a sudden they stop posting completely with no explanation, that's a red flag. Especially, you know, in this generation, everybody's on a phone.

I'm on a phone myself all the time. So having these units for social media, they're huge. It's a vital point of piece of investigative technique now. Let's get a little bit more into what came from Groom's arraignment, okay, and then we're going to break it all down. So Groom appeared in the Taunton County District Court, and this is where he was read as charges. Gregory Groom. Sir, on document, 251816, honor about the date of August 6, 2025 in the town of Rehobot, who charged with murder, assault and battery on a pregnant victim, aggravated intimidation of a witness.

Now, a public defender was appointed to represent him, and a not guilty plea was entered on his behalf. But prosecutors immediately requested that groom be held without bail, and they outlined what is a troubling timeline of events. take a listen. This incident stems from the recovery of the body last evening. The incident started on August 8th when this defendant, Gregory Groom, contacted the Rojovith Police Department to indicate that his ex-girlfriend identified as 18-year-old Kylie Montero was missing. Mr. Groom reported that Ms. Montero was at his house, that she was looking for a place to stay. They got into an argument and that she ultimately left his residence walking down the driveway and she hadn't been

seen or heard from since. Ms. Montero was known to be very active on social media and he hadn't heard from her, neither had her friends or family on any social media in the following days. Investigators say they then combed through her social media activity. They interviewed Groom. They interviewed Kylie's family members. And this uncovered a more alleged troubling picture. Mr. Groom reported that Ms. Montero was approximately 11 weeks pregnant, and she told him that he was the father of the baby, that on August 7th, on August 6, excuse me, she had left a residential program and took a ride share to his house. She was looking to stay with him, and an argument ensued about whether or not he would allow her to stay on his property. when the police began to question him and other family members they learned from miss montero's sister that on august sixth when she had arrived at his house that there was an altercation between mr groom and miss montero miss montero texted a sister that he threw me on the ground and pulled my hair and strangled me my phone is at four percent and if i die it was gregg family members then tried to communicate with Ms. Montero and get her to a place of safety, and she didn't respond right away.

Ultimately, there was a response from her device that indicated she was attempting to continue to stay at Mr. Groom's residence. And the investigation took a very dark turn when Groom was brought in for questioning. During that interview, he admitted that on August 6th, he had gotten into an application with Ms. Montero, where he pushed her, she fell backwards, and she hit her head. When she attempted to contact an individual, Mr. Groom admitted that he knocked her cell phone out of her hands, at which time he was going to be charged

with the three offenses for assault and battery on domestic assault and battery, assault and battery on a pregnant person and for intimidation of a witness. When investigators continued to press Mr. Groom on the whereabouts of Ms. Montero, they informed him that they had applied for and were granted a search warrant

for an extensive search of 107 County Street. That included, only cadaver dogs but excavators chemists from the Massachusetts State Police Crime Lab and other investigators and they informed mr. groom that they were prepared to search the property and dig if necessary mr. groom then paused he was given an opportunity to tell the police where mr. where miss Montero's body was located either by being taken to his property and pointing it out or drawing a map or telling the officers where her body was located as they believe miss

Mr. Groom ultimately drew a rudimentary map indicating that he got into an argument behind a shed on the property where he was known to stay and where Ms. Montaro stayed, that during that altercation, Mr. Groom admitted that he stabbed Ms. Montaro twice in the neck and once in the chest. The stab wound to the chest actually broke the blade of the knife off. He used a kitchen knife to commit the stabbing, and based on that stabbing, Ms. Montaro was deceased. Mr. Groom indicated to the police that he then spent several hours digging the hole in the woods approximately 20 yards from where he killed Ms. Montero. And through the night after he dug, when the sun came up, he then pushed her body into the hole and covered it up. He drew on the map the approximate location of Ms. Montero's remains.

Officers who were conducting the search warrant then went to the shed. They noticed there was a large pile of brush right next to the shed. That was what Mr. Groom used to cover up the site of the murder, to cover up blood that was ultimately recovered, and physical evidence was recovered from the scene where the police alleged the stabbing occurred. About 20 yards away in the woods, there was another large pile of brush with feet upon feet of trees, cut down trees, that were piled up. Underneath that pile, the police located a rectangular hole that appeared that had been recently disturbed dirt. when the police ultimately called in medical examiners to uncover that whole, a body consistent with Kylie Montero was discovered approximately five feet underground.

Ms. Montero's remains were recovered last evening, and her body is at the office of the chief medical examiner undergoing identification process and undergoing an autopsy. Okay, well, from your experience, how common is it for a suspect to report a missing person and then later be implicated in their death, right? Because most people, a lot of people would say, well, wait a minute, if they were responsible, why on earth would they alert authorities? Very common.

As a matter of fact, in most cases that I've dealt with, the person that reports this person missing if they turn up injured or dead is the one that did it. And when you get into some of these initial investigations after someone's reported missing, usually the person that provides the most information and tries to be most helpful is a person you should be looking at, especially in a domestic situation.

And how significant was it that he apparently drew a map for investigators? How does that impact building the case? And just his statements overall, or his alleged statements overall, or, I mean, if you're a prosecutor, this is what you're looking for. If you're an investigator, this is what you're looking for. But what did you make of what he apparently said? I mean, the drawing of the map, when you get into defense, when you start to make a defense into something like that, or even when you're doing questions,

in an interview. You want the person you're questioning to give you details that you don't have. You don't want to feed them details that you have and having to agree with it. You want them to give you details you don't have. Drawing of a map leading to a body, I don't think you get much better evidence than that. And the details about the stabbing, the attempt to conceal the body. This, obviously investigators have to confirm a lot of these details. But if you're talking about trying to elicit that information. A, what is the difficulty in trying to elicit that information from a suspect and, you know, making sure that no rights are violated, that it can be used in a court of law? But also, you know, you wonder why a suspect would

allegedly reveal this information. In a lot of cases, in cases that I've worked, if you have somebody that doesn't ask for a lawyer immediately, there's a chance they want to tell you something. And is the more you question someone, if they keep talking to you they want to say something to you and you have to try to give them an out and what I mean by that is I'm saying you you have to show or you have to say hey listen I know what happened but you got to tell me why this happens so you don't look like an monster or an animal you've got to give your side of the story a lot of times that technique will work because a cold-blooded murderer is going to lawyer up and say nothing someone who may have had

something happened out of sudden and intense passion is going to want to tell you, yeah, listen, I did this, but here are the factors. Here's what happened that led to it. How do investigators confirm things? How do they confirm that, like, for example, the sequence of events when you have an apparent combination of physical assault, a weapon, attempts to cover up the crime? Because timeline matters. Sequence of events matters. Timelines everything. And we talked about social media posting we talk about cell phones tracking of a cell phone last whereabouts last contact she makes with her family when she leaves the residential home all of that stuff folds into a timeline and the timeline is crucial especially when you're

going to get into at the forensics of the postmortem time of death causing manner of death and you kind of pair that with his statements and all that it has to follow in a timeline or to make sense and to be provable to make it a good case, a good prosecutable case. What is this alleged, you know, murder and what is the location of where the remains were found? What does that tell you about what may have happened here? You know, I always wonder sometimes when we have unexplained cases and you think about the discovery of a body who had the opportunity and the means and the resources to transport a body in a particular location. This is such a specific area.

Obviously, the case is I wouldn't want to defend him. I mean, it's really, really tough. It just becomes a question about what does this level of attack and what does where the remains were found and what condition they were in? What does that tell you? Well, it's basically going to tell the story. It's going to say, obviously, he took us to the body. Well, he put it there. That's what you're going to have to prove.

Secondary, when you're talking about defending somebody, you're right. I wouldn't want to defend this person either. So what you're going to have to do, in my opinion, in this case, is you're going to have to say sudden and intense passion, something that you didn't mean to happen, and you're going to try to plead this down off a first-degree murder based on its cooperation, based on the fact that the only defense you can come up with is sudden and intense passion.

I accidentally did this. I lost my mind or whatever. But, I mean, as a prosecutor, they don't get much better than this. And as an investigator, especially when you get a statement that can be corroborated by the physical evidence, it's a horrible situation, but it's a good case. That makes any sense. I always wonder, in your perspective, if you can work out some sort of plea deal where you avoid a trial, is that something, you know, obviously from the victim's case,

I talk about so many time in sexual abuse cases, if you can spare the victims from having to go on the stand and recount? What happened? I mean, that's a goal. If you can spare a jury from grotesque autopsy photos and really disturbing content, obviously I think there's an advantage there. It seems time and expense of a trial. But from an investigative point of view, you put in the work, you maybe would have an opportunity to explain to a jury or judge what the investigation revealed, what the evidence revealed. If this doesn't make it to trial, and there is a plea. deal, and I'm not sure that that's the case and what it would be here. How does law enforcement typically look at that? In a case like this, when you talk about plea deals on a murder, obviously the person who's murdered can't have any input on that. Usually you go to the family. Prosecutors will go to the family. Not always, but they'll go to the family and see if that's something, hey, you want to be spared this. Here's the deal. But the deal's got to make sense. It can't be 10 years. You know what I mean? There's no justice in that.

So I don't like plea deals in cases like this, I wouldn't take a plea. I would want a jury to hear this because it's gruesome. And this guy should never see the light a day again if he's in fact guilty. But sometimes they do make sense. If you do, like you said, spare the family the details, spare everybody the details, and get rid of a long, drawn-out trial if that's what it is. But in my opinion, it's very important that the family has to be on board with any deal before it's given. And the judge doesn't have to accept it either.

No, of course, of course. And I'm not even sure what one would look like here, but talking about the family for a second. So Kylie's family, they had been clinging to hope, you know, that she was alive, that should be found, that she'd be okay. Now they're facing this reality. And her sister, Kitty, shared the following post on Facebook. I'd just like to give a shout out once again to Faith, the Rojobit Police and Massachusetts State Police for their digital. Diligence, dedication, and nonstop hard work in resolving this case. I know this is not the ending we all wanted, but this is closure for us, and this gives Kylie the opportunity to rest in peace with her mom and her baby.

Without you guys, she might not have found peace for years, and that's something that very few people get in cases like these. I think it's a good time to remind everyone to check in regularly with people. Tell them you love them every chance you get. Take photos every single day, and don't ever forget that people love you so many people. Now, a GoFundMe has been set up to help her family with the funeral costs, and the family wrote, thank you all for your help in spreading awareness and for all the support our family has received so far.

This is closure, and we are so thankful for everyone's help in getting there. Obviously, there will be court proceedings, but we are taking this one step at a time. And her sister, Faith, also announced a candlelight vigil will be held in her honor on Saturday, August 23rd. As for Gregory Groom, he remains in custody as the investigation. continues. More details are expected at an upcoming hearing scheduled for September 10th. But will you think about this? If there wasn't such a quick discovery of her remains, let me think about it like this. You have those remains in that specific location. Is there a possibility that they wouldn't have been discovered? And if they were discovered at a later date, could they

have been in a state where you wouldn't have been able to say they are Kylie's or consistent with Kylie? Well, you could probably identify her regardless of when you find are based on, you know, DNA, familial DNA, but the condition of the remains and without getting too graphic, over time with decomposition, with insect involvement, over time you can lose valuable evidence. Now, I believe I read that the, he said he broke the blade off inside of her. That's not going anywhere that that would be there regardless um but you do you can't absolutely lose physical evidence as time goes by um it was like we talked about this earlier it was huge that he brought investigators to the to the grade because it's 20 yards away from the will all of it happen

weather comes in you lose a ton of physical evidence because of the weather the rain or whatever can wash away all your blood evidence so the time is you're not you're going to crucial the further you go out the more physical evidence you're going to lose so the time frame in this was crucial and what a wonderful heartfelt statement the sister put out on that just just a wonderful statement and law enforcement we like to we like to hear that um i guess that were appreciated but it's not about us it's about this family how do you guide a family that lost a loved one through the process, right? First, you have to alert them to the fact that these human remains were discovered, but now they have to go through the next phase, right? They have to go through, aside from just

their grief and trying to make sense of all this, now they have to go through the legal process. And if Mr. Groom decides to move forward and he decides to fight this and he decides to take this to trial, that can be a very difficult emotional journey. What role does law enforcement play in communicating to the family and being there for the family. Whatever you have to do. I mean, it's not just you're done with it. We got them charged. You wash your hand to it.

You're part of that entire process up until the prosecution of the case and then the disposition of the case. You're part of it. And I don't know any good homicide investigator who isn't, and I don't want to say emotionally involved, but at least interested in what happens with the family going through this. We know what happens through a trial. 99% of the people, fortunately, don't have to go through it. And what happens leading up to the trial, the various motions.

There's going to be, they listen to what the complaint was today in court. They listen to what the basis they used for the charges were. You have to get the elements of all your charges. So they heard that. If this goes to trial and further, they're going to see photographs like you spoke of. And then there's going to be testimony from medical examiners and investigators and what they saw. And that's brutal. And people and families, and you talk about closure, I'm not sure what that means.

It's not going to get easy for this family. It might get easier, but it'll never be easy. And as law enforcement officials, if you're worth your salt as an investigator, you're going to help the family get through this process. Well, Sveilar, thank you so much for taking the time. Really difficult to update, really difficult case, but really appreciate it. Thank you. You're welcome.

Anytime. All right, everybody. that's all we have for you right now here on Sidebar. Thank you so much for joining us. And as always, please subscribe on YouTube, Apple Podcasts, Spotify, wherever you should get your podcasts. I'm Jesse Weber. I'll speak to you next time. Wondery Plus in the Wondery app, Apple Podcasts, or Spotify.