‘If I Die, It Was Greg’: Chilling Texts Just Revealed in Pregnant Teen’s Murder

Miss Monto texted a sister. that he threw me on the ground and. pulled my hair and strangled and. strangled me. My phone is at 4% and if I. die, it was Greg. A grim and shilling. turn in the disappearance of 18-year-old. Kylie Montero. Her boyfriend, 22-year-old Gregory Groom, has been. arrested and charged 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. [Music]. 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 Taton. 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. This. tragic and sad development comes after. nearly two weeks of intensive searches. across Raobith, a small town in Bristol. County, Massachusetts, about 50 miles.

from Boston. Now, the search efforts. involved drones, cadaavver 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 6. According to Kylie's family, she. reportedly had some sort of altercation. with Groom at his home. And at the time, there were 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 groom.

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 Tik. Tok, and eerily, her last post was on. August 6, a photo caption in abbreviated. form, "I don't care what people think. about me." For more than a week, Rahobit. police and the Massachusetts State. Police conducted tireless searches for. her. Again, deploying K-9 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. Attabboroough High School graduate had. just celebrated receiving her diploma. She was roughly 11 weeks pregnant. And. they also share 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.

or 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 a 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, Rahobit Police Chief Lewis. Tabico and investigators addressed the. just tragic development at a press.

conference. Uh 18-year-old Tylie. Monttero was reported missing but 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 Rahobath. uh which is the residence of Gregory. Groom. There's also learned that Kylie. Monttero 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 Rahobit that was executed. starting this afternoon. As a result of the search of the. property, human remains consistent with those of. Kylie Monttero 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 Selar, a retired. detective commander from the Chicago. Police Department. Uh Will, thank you so. much for coming on. Um this is a really. really sad uh development. From your. experience, what are the challenges for. investigators? What do they face when. searching for a missing person um on. private property, especially when you're. dealing with human remains uh being.

involved? Well, >> it's a terrible story. It's a terrible. story with uh you know, your updates. today with the with the charges 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 Broom 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 cadaavver dogs, the dive teams, the back hose. Is that. typical in an investigation like this? How extensive is that? >> It's pretty extensive. It's u but you're. also dealing with a large property. I. think it was like 25 acres of property. that they were dealing with. So, if you. have whatever resource you have, you use. it. especially you got an 18-year-old. who's pregnant, obviously high risk, uh,

living in a shelter, not the best. support system that you could think of, you 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, um, 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. This is America's. largest injury law firm. This is a firm.

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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 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. or keep a better eye on uh the girl. who's pregnant, especially when she's 18. years old. She's in a relationship with. a man who may or may not want the. pregnancy. And there may probably have.

been mentions, some kind of mentioning. of uh domestic violence in the past to. her friends. So there there's a lot of. red flags. Obviously, physical. condition. if you see any kind of. bruises or or scrapes, uh, you got to. pay attention to that. But I think the. key factor in this one's going to be the. pregnancy. >> Yeah. And 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 uh. apparent social media post um from Kylie. as well. Um, 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 times about how. you can't really believe anything on. social media. People put one image on. there, but um but in but truth be told, it can really help with investigations, particularly missing persons. investigations, right? >> Oh, massive. It it's 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. someone 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 the phone myself all the. time. So, u having these units for. social media, they're huge. It's it's a. vital point uh piece of investigative uh. technique. Now, >> let's get a little bit more into what. came from groom's arraignment, okay? Okay. And then we're going to break it. all down. So Groom appeared in the Taton.

County District Court and this is where. he was read his charges. >> Gregory Groom. [Music]. on 25 1816 honorable the date of August. 6, 2025 in the town of Rehovven.

with murder, assault and battery at a. pregnant victim, aggravated intimidation. of a witness. >> Now, a public defender was appointed to. represent him and a not-uilty 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 a body last evening. Uh the. incident uh started on.

August 8th when this defendant, Gregory. Groom, contacted the Rahobit Police. Department to indicate that his. ex-girlfriend, identified as 18-year-old. Kylie Montero, uh was missing. Mr. Groom. reported that Miss Montero was at his. house, that she was looking for a place. to stay. they got into an argument and. that uh she ultimately left his. residence walking down the driveway and. she hadn't been seen or heard from. since. Miss 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 uh in the. following days. >> Investigators say they then comb through. her social media activity. They. interviewed Groom. They interviewed. Kylie's family members and this. uncovered a more alleged troubling. picture. >> Mr. room reported that uh Miss Montero. was approximately 11 weeks pregnant and. she told him that he was the father of. the baby that on August 7th she on. August 6th, excuse me, uh she had left a.

uh 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 on his property. when uh the police began to question him. and other family members, they learned. from uh Miss Monto's sister that on. August 6th when she had arrived at his. house uh 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 and. strangled me. My phone is at 4% and if I. die, it was Greg. Family members then. tried to communicate with Miss 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. altercation with Miss Montero where he. pushed her. She fell backwards and she. hit her head. When she attempted to. contact uh an individual, Mr. Groom. admitted that he knocked her cell phone. out of her hand, at which time he was. going to be charged with a three. offenses for assault and battery on uh. 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 Miss.

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 not only. cadaavver 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. believed Miss Montero was dead. Uh, Mr. Groom ultimately drew a rudimentary map. indicating that he got into an argument. uh behind a shed on the property where. he was known to stay and where Miss. Montero stayed. That during that. altercation, Mr. Groom admitted that he. stabbed Miss Montero, 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. uh to commit the stabbing and based on. that stabbing, Miss Montero was. deceased. Mr. Groom indicated to police. that he then spent several hours digging. a hole in the woods approximately 20. yards from where he killed Miss Montero. and uh 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 Miss Montero's remains. Officers who.

were conducting the search warrant then. went to the shed. They noticed there was. a large uh pile of brush uh right next. to the shed. That was what Mr. uh groom. used to cover up the sight of the murder. uh 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 uh 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 uh ultimately called in medical. examiners to uh uncover that hole, uh a. body consistent with Kylie Montero was. discovered approximately five feet uh. underground. Miss 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. Will, 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 then 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 the 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 and how significant was it that he. apparently drew a map uh for. investigators? You know, how does that. impact building the case? And just his. statements overall or his alleged. statements overall are I mean, if you're. a prosecutor, this is what you're. looking for. or 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 a defense, when you start to. make a defense into something like that,

or even when you're doing questioning 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 have them 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 and. the details about the stabbing, the. attempt to conceal the body. Um, this. obviously investigators have to confirm. a lot of the 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 from a suspect and, you. know, making sure that no rights are. violated, that it can be used in a court. of law. Um, 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 happened so. you don't look like an a monster or an. animal. You got to give your side of the. story. A lot of times that technique. will work because, you know, a. cold-blooded murderer is going to lawyer. up and say nothing. Someone who may have. had something happen out of a sudden and.

intense passion is going to want to tell. you, "Yeah, listen. I did this, but but. here are the factors. Here's what. happened that led to it.". >> Yeah. 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. >> Timeline's everything. Uh, and and we. talked about social media posting. You. talk about cell phones, uh tracking of a.

cell phone, last whereabouts, last. contact she makes with her family when. she leaves the uh 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 u the post-mortem time. of death, cause and manner of death. And. you kind of pair that with his. statements and all of it has to follow. in a timeline for it to make sense and. to be provable to make it a good case, a.

good prosecutable case. What is this uh alleged, you know, murder and what is the the location of. where the remains were found? What does. that tell you about what may have. happened here? Um, 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. it it 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 um and what does where. the remains were found and what. condition they were in. What does that. tell you? >> Well, it's going to it's basically going. to tell the story. It's going to say. obviously he took us to the body but he. put it there. Uh 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 it's sudden and intense passion, something that he didn't mean to happen, and you're going to try to plead this. down off of first-degree murder based on. his cooperation, based on the fact that. um 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 investigator, especially when you. get a statement that can be cooperated. 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, um, I talked about this. 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 a goal. you. can spare a jury from grotesque autopsy. photos and really disturbing content. Obviously, I think there's an advantage. there. Sames time and expense of a.

trial. But from an investigative point. of view, you put in the work. Um, 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. Um, 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, um, 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. >> Yeah. >> Because it's gruesome. This guy should. never see the light of day again if he's. in fact guilty. Um, but sometimes they.

do make sense if you if you do, like you. said, spare the family the details, spare everybody the details, and, you. know, get rid of a long drawn out trial. if 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. Um, 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 she'd 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 Rahobit Police, and. Massachusetts State Police for their. diligence, dedication, and non-stop 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 uh for. September 10th. But will you think about. this if there wasn't such a quick. discovery of her remains? Let let me. think about it like this. You have those remains in that specific.

location. Um, 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 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 her based. on, you know, DNA, familial DNA. Um, 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 I believe I. read that the 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. 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 to the grave. because it's 20 yards away from the.

where all of it happened. Weather comes. in, you lose a ton of physical evidence. because of the weather, the rain or. whatever and wash away all your blood. evidence. So, the time is crucial. The. further you go out, the more physical. evidence you're going to lose. So, the. the time frame in this was crucial. And. what a wonderful u heartfelt statement u. 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 we're 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 grief and trying to make sense of. all this. Now they have to go through. the legal process and if uh 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 him. 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.

um 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. So, you have to get. the elements of all the both of 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, you talk about. closure, not sure what that means. Um, it's not gonna it's it's not going to. get easy for this family. Might get. easier, but it'll never be easy. And uh, as law enforcement officials, if you're. worth your salt as a as an investigator, you're going to help the family get. through this process. >> Well, Sar, thank you so much for taking. the time. Uh, really difficult update,

really difficult t, 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 Podcast, Spotify, wherever you. should get your podcasts. I'm Jesse. Weber. I'll speak to you next time. [Music].