Search Captions & Ask AI

An online love triangle leads to a deadly crime

November 11, 2023 / 51:26

This episode covers the online relationship between Tom Montgomery, a 46-year-old man posing as an 18-year-old Marine named Tommy, and Jesse, an 18-year-old girl. It discusses themes of deception, manipulation, and the tragic consequences of their interactions, including the murder of Brian Barrett, a young man caught in the middle.

Tom Montgomery, using the alias Tommy, created a false identity to engage with Jesse on the gaming platform Pogo. He shared fabricated stories about his life, including his upcoming deployment to Iraq, which led to a romantic relationship filled with cyber intimacy.

As the relationship progressed, Montgomery's wife, Cindy, discovered the deception and wrote to Jesse, revealing that Tommy was actually her husband. This revelation led to a fallout between Jesse and Montgomery, who became increasingly jealous and threatening, particularly towards Jesse's new friend, Brian Barrett.

Brian was ultimately murdered by Montgomery, who was charged with first-degree manslaughter. The episode highlights the dangers of online relationships and the impact of fantasy on real-life actions.

The story concludes with the aftermath of the murder, the consequences for both Montgomery and Jesse, and the ongoing discussions about accountability in online interactions.

TLDR

Tom Montgomery, posing as a teen, deceives Jesse, leading to a tragic love triangle and the murder of Brian Barrett.

Episode

51:26
00:00:09
[Music] our episodes deal with serious and often distressing incidents if you feel at any
00:00:18
time you need support please contact your local crisis center for suggested phone numbers for confidential support
00:00:26
and for a more detailed list of content warnings please the show notes for this episode on your app or on our
00:00:39
website pogo.com is an online gaming site that provides a platform for strangers and friends to gather together
00:00:46
to play a variety of card and board games users enter particular rooms to play the game of their choice and as
00:00:54
they play they can also chat by typing messages to other users in April 2005 a user with the name
00:01:03
marine sniper was playing blackjack in one of pogo's rooms when he received a message from another player going by the
00:01:10
name tall hot blonde big 50 tall hot blonde introduced herself as 18-year-old Jesse she then informed
00:01:19
marine sniper that he was in the wrong place the room they were in was for teenagers and marine sniper profile
00:01:27
clearly stated that he was 46 6 years old marine sniper reassured Jesse that he wasn't in the wrong room he was
00:01:37
actually 18 like her but he was using his father's account to play That's why his profile had him as
00:01:46
46 with that issue addressed and out of the way tall hot blonde and marine sniper were free to keep messaging one
00:01:58
another [Music] it didn't take long for marine sniper to start sharing more information about
00:02:25
himself with the Jesse his real name was Tommy and he lived in Upstate New York near the City
00:02:32
of Buffalo Tommy had Big Dreams he was set to join the Marines like his father and
00:02:39
wanted to become the best and toughest version of himself he could be Tommy hadn't always felt this way he
00:02:48
told Jesse that when he was 12 his mother died of cancer and after this he never felt love from another person
00:02:56
again after being betrayed by a couple of different people Tommy gradually began to switch off his feelings and
00:03:03
became a loner he sometimes thought about taking his own life but directed his pain and
00:03:09
self-hatred outwards instead when he was 17 he raped a cheerleader from his high
00:03:17
school Tommy explained that he'd reached rock bottom and experienced a sense of total
00:03:23
hopelessness he'd found Purpose By enlisting in the Marines and was getting ready to attend boot camp in two months
00:03:31
time Tommy would head to Paris Island in South Carolina to undertake his training Jesse wasn't totally horrified
00:03:40
by Tommy's admission that he was a rapist instead she felt compassion for what he'd been through and told him she
00:03:46
was proud that he'd worked to better himself she knew what it was like to feel a lack of
00:03:54
Direction Jesse lived in the state of West Virginia in a small town called Oak Hill
00:04:00
her life was fairly typical she lived with her parents and younger brother but often fought with her
00:04:07
mom Jesse loved Sports and played softball and basketball for extra money she worked part-time as a
00:04:15
lifeguard Jesse was in her final year of high school and getting ready to graduate she was set to go to college
00:04:22
but didn't really know what she wanted to do with her life in Tommy Jesse saw the chance for
00:04:29
exciting future during their very first conversation Jesse sent Tommy some bikini clad photos of
00:04:42
herself just as her Pogo username implied she was tall and athletic with tanned skin and a long blonde
00:04:49
hair more pictures soon followed there were glamour shots that had been taken by professional
00:04:56
photographers as well as more relaxed candid photos of Jesse playing sports Jesse began making photo
00:05:04
slideshows for Tommy set to backgrounds of romantic power ballads such as Aeros Smiths I Don't Want to Miss a
00:05:12
Thing Jesse was curious to know what Tommy looked like he described himself as 6 tall and muscular with big
00:05:21
shoulders Jesse was pleased by this she liked big shoulders eventually Tommy sent Jesse a
00:05:29
photo of himself wearing his Cadet uniform and a Stern expression Jesse thought he looked
00:05:37
handsome as the days went by Jesse and Tommy chatted more and more they communicated by instant message on Pogo
00:05:46
as well as via email and Yahoo eventually the two exchanged phone numbers and began talking over the phone
00:05:54
as well when Tommy headed to South Carolina for boot camp his time time became somewhat limited but he always made time
00:06:02
to talk with the Jesse it wasn't long before the two teenagers declared their love for each
00:06:11
other their conversations became raer and they engaged in cyber sex Tommy told Jesse that he'd gotten a
00:06:20
tattooo on his arm in honor of their relationship it featured the words always and forever alongside a heart
00:06:28
with the Jesse's name inside always and forever was both a nod to the Marines motto simpa Fidelis and a
00:06:36
special saying that Tommy and Jesse used to refer to their love after Tommy's boot camp training
00:06:44
was complete he received a word that he was being deployed to fight in the Iraq War which the United States had
00:06:50
initiated more than 2 years earlier he told Jesse that his internet access would be restricted during this
00:06:57
time if she need needed to reach him urgently while he was out on a Dangerous Mission or wanted to send him a care
00:07:04
package she could do so via his father Tom Senor Tom senior's Marine contacts meant
00:07:11
he could get packages delivered to Iraq faster than the US Postal Service Jesse sent Tom Senor letters and
00:07:19
photographs which he forwarded to his son but being far away from Jesse and unable to see her in person ignited
00:07:28
Tommy's jealous streak he accused her of flirting with other men from their Gaming Community and
00:07:34
sending them pictures this led to the young couple's first argument eager for them to make up Jesse
00:07:42
sent Tommy a special parcel that included a necklace with a pendant in the shape of half a heart she kept the
00:07:50
other half for herself Jesse also included a pair of her underwear Tommy got over there brief
00:07:59
argument but his father didn't Tom senior didn't agree with Tommy and Jesse's relationship he discouraged Jesse from
00:08:08
pursuing his son any further telling her he would no longer relay any messages between the
00:08:14
couple he thought the relationship should end and told Jesse quote you will hurt him and he's an
00:08:22
idiot and will believe your lying ass Jesse wasn't dissuaded she continued contacting Tommy telling him she was
00:08:35
worried about his safety while he was fighting in Iraq in one message she wrote I know you're being careful honey
00:08:44
and you have the best with you but I also know anything can happen Tommy kept replying to Jesse
00:08:52
reassuring her and saying she was the best thing that ever happened to him he also told her about the battles he was
00:08:59
fighting in the Iraqi city of fuah as December rolled around the couple had been in contact for roughly 8
00:09:09
months at Christmas Tommy surprised Jesse by proposing to her she accepted to mark their engagement Tommy
00:09:20
sent Jesse some red Point sanas flowers that are popular at Christmas time Jesse mailed Tommy another care
00:09:28
package with more of her underwear as well as dog tags engraved with the words Tom and Jesse always and
00:09:38
forever the couple agreed to marry when Tommy returned home from Iraq Jesse wrote excitedly about how she
00:09:46
would take Tommy's last name which was Montgomery she also imagined what their wedding night would be
00:09:53
like in their Communications to each other they talked about how their future together would be incredibly
00:10:02
bright 2 months later in February 2006 Jesse received an envelope in the mail inside was what appeared to be a
00:10:12
family photograph taken in a professional studio a middle-aged woman with shoulder
00:10:18
length of dark blonde hair stood in the center sitting behind her was a middle-aged boarding man wearing
00:10:25
glasses on either side of the couple stood two girls who looked to be in their early to mid
00:10:31
[Music] teens along with the photo was a handwritten letter it opened with the words Jesse in closed you will find a
00:10:43
picture of my family let me introduce you to these people the man in the center is Tom my
00:10:53
husband the writer explained that her name was Cindy Montgomery and she was the woman in the
00:10:59
picture the two girls were their daughters who were aged 12 and 14 Cindy explained that she and Tom
00:11:08
didn't have any sons Tommy the young Cadet Jesse had been having a relationship with for almost a year
00:11:16
didn't exist Jesse had been speaking to 46-year-old Tom the entire time Cindy had uncovered the ruse when
00:11:27
she stumbled across some of Jesse's letters to Tommy which Tom had stashed away Cindy was concerned for the young
00:11:36
woman and decided to let her know what had been going on she closed her letter with the
00:11:41
following message from what I am pulling from your letters you are much closer to my
00:11:48
daughter's age than mine let alone Tom's are you over the age of 18 in this alone he can be prosecuted as
00:11:57
a child predator he is taking advantage of you you need to be much more cautious
00:12:03
with your safety you will only be hurt by a man who has mastered the art of manipulation and lies do not trust words
00:12:11
on a [Music] computer as a young man in the 1970s Tom Montgomery had enlisted in the Marines
00:12:24
but he never saw active combat by the time he was discharged he developed a drinking
00:12:30
problem when he married Cindy and had his first daughter Montgomery found the motivation he needed to address his
00:12:37
addiction a few years later he and Cindy welcomed their second child Tom Montgomery became a dedicated
00:12:45
father who volunteered with his daughter's swimming club and taught Sunday school at the family's
00:12:51
church he provided for his family by working as a machinist at Diner a power tool company with headquarters in the
00:12:58
New York town of Clarence the job didn't engage him in the same way that the military did but
00:13:05
he made a go of it and became friends with some of his co-workers over the years Montgomery
00:13:12
began to struggle again he had difficulties with erectile dysfunction and his marriage suffered both
00:13:19
physically and emotionally communication between him and Cindy dropped to an alltime low and
00:13:25
Montgomery sought refuge on the internet he spent countless hours in online gaming rooms playing games and chatting
00:13:34
with strangers as it was easier confiding in people he didn't know via words on a
00:13:40
screen Montgomery was careful not to share any information about his wife and daughters but he opened up about some of
00:13:47
his problems with the other Gamers he met the first time Jesse reached out to him in pogo's blackjack room Montgomery
00:13:57
was enticed by the thought thought of an attractive young woman but when Jesse asked why he was in
00:14:03
a room for kids when his profile listed him as 46 Montgomery panicked he'd heard about sting
00:14:11
operations where undercover agents infiltrated online spaces looking for sexual predators acting on impulse Montgomery
00:14:19
lied to Jesse telling her he was 18 and using his dad's account when Jesse sent him photos of
00:14:28
herself wearing swimsuits he was entranced he began concocting the character of Tommy so he could keep
00:14:35
talking with her Montgomery made up stories about Tommy's past and gave his altero a troubled background to help win
00:14:43
Jesse's sympathy the photo he'd sent her was actually a 30-year-old photo of Montgomery in his own Marine's
00:14:53
uniform as time passed Montgomery battled with whether or not he should put a stop to these Antics he created
00:15:01
the personality of Tommy's father to maintain contact with the Jesse even when Tommy was supposedly on dangerous
00:15:07
missions with the Marines but he also used this Persona to try to break things off between the
00:15:15
teenages ultimately it didn't work his obsession with his Fantasy Life was too strong Cindy Montgomery noticed her
00:15:27
husband's fixation with the internet he would kick their daughters off the computer so he could use it himself and
00:15:33
then stay up typing well into the night the truth was exposed in February 2006 when Cindy stumbled across a parcel
00:15:43
Jesse had sent her husband inside was a letter and some red underwear that clearly belonged to a
00:15:50
teenage girl Cindy was disgusted and horrified to learn what Montgomery had done Not
00:15:58
only was he lying to her and their children he was also manipulating an 18-year-old Cindy confronted her husband
00:16:06
and the couple agreed to divorce in the meantime Montgomery would move into the basement Cindy was disturbed by the
00:16:16
thought that Jesse was blissfully unaware that her young fiance was actually a middle-aged
00:16:22
man as a mother to young girls herself she felt she had to do something Cindy wrote a letter to Jesse and posted it to
00:16:31
the return address listed on the parcel exposing all of Tom Montgomery's lies after Jesse read the letter she
00:16:43
immediately sent Montgomery an angry text message telling him he should be in jail the pair then met in a private chat
00:16:52
room Jesse was Furious and hurt she asked Montgomery why he'd done what he did Montgomery couldn't provide a
00:17:01
satisfactory answer he said he wished he could explain it but he didn't have any
00:17:07
answers he'd planned to kill Tommy off by saying he'd had died during combat in Iraq but Cindy had discovered his secret
00:17:15
before he had the chance Jesse didn't know what to think she decided to reach out to a third
00:17:23
party who might be able to shed some light on the situation recalled that Montgomery had
00:17:30
mentioned a friend of his named Brian who was also active on Pogo she even remembered Brian's
00:17:36
username Beefcake 1572 22-year-old Brian Barrett was a college student who worked part-time
00:17:47
with Tom Montgomery at Diner braid to pay for his tuition he still lived at home with his
00:17:53
parents and 15-year-old brother every weekday Brian got up at at 6:30 a.m. spent the day at college and
00:18:01
then headed straight to diner braid for an evening shift that finished at 10:00 p.m. Jesse sent Brian a message telling
00:18:10
him what Montgomery had done Brian was shocked by his co-workers actions and provided Jesse with a
00:18:17
sympathetic ear the two began messaging each other often growing closer and closer Jesse was just Brian's type Not
00:18:28
only was he attracted to blondes he'd played football and baseball in school and he found Jesse's athleticism very
00:18:36
appealing just as she'd done with Tommy Jesse sent Brian photos of herself and handwritten cards telling him how much
00:18:43
he meant to her it wasn't long before the two declared their love for one another the pair also bounded over their
00:18:55
disgust at Tom Montgomery they went to into the online chat rooms he frequented and told others
00:19:01
what he'd done calling him a loser and a predator as a result Montgomery was temporarily suspended from playing on
00:19:10
Pogo Jesse also shared her login details with Brian so that he could use her account to pose as her and send
00:19:18
Montgomery mocking messages Jesse and Brian decided that Montgomery's colleagues needed to know
00:19:25
about this inidan as well they debated how Brian should tell them with Brian asking
00:19:32
Jesse what should I say up to you baby she replied I have to [ __ ] with him Brian typed to back you are so bad Jesse
00:19:45
answered Brian told people at Diner braid what Montgomery had been up to and left printouts of Montgomery into
00:19:52
Jesse's conversations lying around the factory Montgomery's colleagues were were aware he'd been flirting with a
00:19:59
much younger woman as he'd been bragging about his relationship with the Jesse for months but they didn't know that
00:20:05
he'd been lying and posing as a teenager The Fallout was Swift a furious Montgomery sent Jesse a
00:20:15
private message letting her know that because of her and Brian's actions many of his co-workers thought he was a
00:20:21
sexual predator people no longer trusted him to be around their kids as far as Tom Montgomery was
00:20:30
concerned his life had been [Music] destroyed Montgomery told both Brian and Jesse to leave him alone he would no
00:20:43
longer talk to Brian online or when they crossed paths at work when Brian told other colleagues
00:20:50
that he hoped to drive down to West Virginia to meet up with the Jesse the news made its way back to
00:20:57
Montgomery this upset him even more he knew that Jesse was a virgin and he was fixated with the idea of being
00:21:05
her first now it sounded like she was planning to have sex with Brian but Jesse wasn't done with Tom
00:21:16
Montgomery after two weeks of Silence she began messaging him again saying that she missed the Tommy Alter
00:21:24
Ego Jesse explained that she had truly fallen in love with the 18-year-old marine sniper she'd believed was
00:21:32
real she'd never felt the same way about Brian and had only really flirted with him to get revenge against
00:21:40
Montgomery the Revelation that Tommy never existed had left her in Despair and unable to believe in true love she
00:21:48
believed quote if he existed I would still be holding him every night and sharing dreams with him every
00:21:57
night Tom Montgomery found himself drawn back in he alternated between making hostile
00:22:05
digs about Jesse's relationship with Brian and apologizing for having lied to her Jesse asked if they could be
00:22:14
friends Montgomery was her only connection to Tommy whom she still loved Montgomery admitted he missed
00:22:23
Tommy too typing I still feel Tommy in my heart he added that he had never stopped
00:22:31
caring for Jesse the two agreed to start over as friends the new friendship was fragile
00:22:40
and fraught with issues from the GetGo for starters it was clear that Montgomery still wanted a romantic
00:22:47
relationship with the Jesse during their long late night chat sessions he sent her self-pitying
00:22:54
messages about how he wanted more than she could give whenever he caught wind of Jesse's
00:23:00
online friendships with other men Montgomery's sweet tone switched in an instant he'd send Jesse a barrage of
00:23:08
angry messages calling her a [ __ ] and using racial slurs as he described how he hoped she would be raped by black
00:23:16
men Montgomery stalked Jesse's account on the social media networking site Myspace and grilled her about who she'd
00:23:24
been talking to he reserved a l portion of his rage for his colleague Brian Barrett Montgomery told
00:23:34
Jesse I hate him with a passion and for 10 cents I would eliminate him Jesse replied that's a little drastic isn't
00:23:44
it Montgomery responded payback is a [ __ ] Jesse I am the Ultimate Weapon I am a
00:23:53
marine Brian will pay him blood Montgomery also had a confession for Jesse after Brian outed his catfishing
00:24:04
of Jesse to their colleagues Montgomery had seriously considered shooting him despite these threats and admissions
00:24:13
Jesse said nothing to Brian or the police instead she merely promised Montgomery that she wouldn't talk to
00:24:20
Brian again over the following few months Jesse and Montgomery's relationship fell
00:24:29
into a toxic pattern sometimes they'd get along and even engage in roleplay where Montgomery
00:24:36
pretended to be Tommy again during which they'd engage in cyber sex at the same time Jesse continued to
00:24:44
message other men Montgomery found out about this through their online community and was
00:24:50
riddled with a jealousy he sent Jesse abusive messages threatening to publish her address online
00:24:59
eventually Montgomery told Jesse that if she didn't leave him alone he traveled to West Virginia and physically heard
00:25:06
her he also made a Veiled Threat against Jesse's mother Jesse backed off but only for a
00:25:16
while she soon reached out again explaining to Montgomery that her mother Mary wanted to speak to him Mary then
00:25:24
contacted Montgomery and demanded he stay away from her daughter Montgomery agreed but told Mary
00:25:32
he also wanted Jesse to stay away from him a couple of weeks went by before Jesse sent Montgomery another
00:25:42
message he pointed out that her mother had forbidden her from speaking to him but Jesse Shrugged it off writing well
00:25:51
she'll never know Jesse had promised mon Montgomery she was no longer speaking to Brian
00:26:00
Barrett but in September 2006 Montgomery was looking at Jesse's Myspace page when
00:26:06
he noticed something enraging Brian Barrett was listed as one of her friends and the two had been
00:26:13
messaging each other there Montgomery confronted Jesse asking if she and Brian were back
00:26:21
together I can handle you with anyone but him he messaged Jess he insisted that the two
00:26:28
weren't together but had just talked but there was someone else Jesse had met a new guy who went by
00:26:37
the nickname shake and she thought the two of them had something special Montgomery didn't believe her he
00:26:46
was convinced that shake was actually Brian and that the two were in a romantic relationship Montgomery also believed
00:26:54
that Brian had plans to drive down to West Virginia in 2 months time to spend Thanksgiving with the
00:27:01
Jesse you better be very afraid now he warned I told you what would happen if you and Brian got
00:27:09
together at around midnight on Wednesday September 133 2006 Jesse and Montgomery
00:27:16
began chatting online Jesse repeatedly insisted that shake and Brian were not the same person
00:27:23
and asked Montgomery to leave her alone she told him I'm asking you to love me enough to let me
00:27:33
go Jesse announced that she was going to delete her accounts on Pogo and Yahoo before signing off with one final
00:27:42
message I love you and will miss you Tom goodbye baby I'm leaving now at 1:36 a.m. Montgomery replied
00:27:53
quote run to Brian you coor he is waiting for you 4 hours later Montgomery checked
00:28:03
back online to see if Jesse had indeed deleted her profiles she hadn't he sent her several
00:28:11
abusive messages calling her a liar then he messaged Brian stating your girlfriend is just like you
00:28:20
nothing but lies keep her the [ __ ] away from me you wanted her you got her [Music]
00:28:36
on the morning of Sunday September 17 2006 Brian Barrett's parents and younger brother walked through the door of their
00:28:43
home in Lockport New York and immediately knew something was wrong the trio had spent the weekend
00:28:50
camping with some family friends while 22-year-old Brian stayed at home but there was no no sign of Brian
00:28:58
anywhere and it was clear that the family's cats hadn't been fed in a couple of days this was completely unlike Brian
00:29:06
who was typically reliable and responsible even if he'd planned to go out he would have made sure to feed the
00:29:15
pets roughly an hour later there was a knock at the front door when Brian's father Daniel Barrett went to answer it
00:29:23
he saw officers from the local police department standing there realizing something must have happened
00:29:29
to his son Daniel immediately began to scream about 36 hours earlier at 10:16 p.m. on Friday September 15 Brian
00:29:43
Barrett finished his shift at Diner braak he punched out and headed towards his white Ford Ranger truck which was
00:29:50
parked near the back of the employee parking lot he climbed behind the wheel and Was
00:29:56
preparing to leave when the sharp sound of gunshots pierced the night air the driver's side window was shot at
00:30:04
three times shattering the glass one of the bullets landed in Brian's upper left arm while the other
00:30:10
two went into his neck he slumped over towards the passenger seat dead because Brian's family was away and
00:30:22
no one was at the diner bra Factory over the weekend it took 2 days before he body was
00:30:29
discovered detectives found Witnesses who'd heard the gunshots and seen an individual dressed in camouflage and a
00:30:36
ski mask lurking in the area this along with Brian's time card helped to narrow down the time of the
00:30:44
murder the killer had used a 30 caliber carbine rifle but there was no sign of the spent shell casings the only Clues
00:30:53
recovered were a gun clip with what appeared to be dog hairs on it and a Peach Pit which was found lying
00:31:00
nearby to police the crime looked like a sniper style shooting Brian's family members couldn't
00:31:09
imagine who would want to harm the 22-year-old Brian was a happy go-lucky well-liked young man with no known
00:31:18
enemies but his co-workers told police about the bizarre online love triangle involving Brian Tom Montgomery and an
00:31:26
18-year-old girl they said that not only had Montgomery been badmouthing Brian for
00:31:32
months he'd recently made some disturbing comments according to one colleague Montgomery said that if he ever killed
00:31:41
someone he'd use an M1 A1 military rifle and wouldn't be stupid enough to leave any showc casings lying
00:31:49
around this was significant given that the bullets found in Brian's Body matched this type of
00:31:56
rifle a according to the colleague Montgomery had also made inquiries about what time Brian's shifts
00:32:04
ended investigators were eager to speak to Tom Montgomery for themselves but they couldn't track him
00:32:11
down they began to worry that perhaps Montgomery had left the state to take revenge against Jesse as
00:32:22
well using a number saved in Brian's cell phone officers were able to reach Jesse she was safe and
00:32:30
well Jesse confirmed that she'd been involved with both Brian Barrett and Tom Montgomery and that she'd been
00:32:37
increasingly concerned about Montgomery's erratic Behavior according to Jesse Brian told
00:32:44
her that Montgomery had tried to hit him with his car in their work parking lot on several
00:32:50
occasions he never spoke or made eye contact just sat behind the wheel with a Stony expression on his
00:32:58
face when Jesse warned Brian that Montgomery was making violent threats against him Brian asked if he should
00:33:05
report this to his boss or another coworker Jesse didn't directly reply instead saying she was very scared of
00:33:15
Montgomery Brian replied yeah me too he's crazy the last that Jesse had heard from
00:33:25
Tom Montgomery was on Friday's September 15 having finally cut ties with him 2 days prior Montgomery had continued to
00:33:33
message her saying things like hey [ __ ] you suck your boyfriend Brian's [ __ ]
00:33:41
today Jesse never replied early on Friday morning she awoke to the sound of her cell phone
00:33:48
ringing Tom Montgomery was on the other line screaming obscenities in a wild rage Jesse hung up on him but he'd
00:33:57
reached out again later that night about an hour and a half after Brian Barrett was
00:34:03
killed Jesse received an online message from Montgomery asking you waiting for your
00:34:10
boyfriend just over 2 hours later he tried again typing come on Brian won't mind you
00:34:18
talking to me or are you talking to your boyfriend here officers in New York were worried
00:34:27
that Jesse might be in danger they contacted the police in West Virginia and asked them to visit Jesse at
00:34:36
home at around 6:00 a.m. officer Lee Kirk and his partner arrived at the address Jesse
00:34:44
provided it was a white house with peeling paint in the small town of Oak Hill a short middle-aged woman with a
00:34:52
bobbed haircut answered the door she identified herself as is 45-year-old Mary Sheila the officers asked if anyone
00:35:02
named to Jesse lived at the home Mary replied that her daughter Jesse no longer resided there as she was away at
00:35:10
College officer Kirk reported this back to the police in New York who told him they'd spoken with the Jesse just hours
00:35:18
earlier and she'd told them she wasn't home officer Kirk returned to the house and asked Mary if Jesse had had been
00:35:27
home recently Mary said no she didn't have a phone number for Jesse either officer Kirk found this hard to
00:35:38
believe he told Mary they were concerned that her daughter could be in danger and
00:35:43
they needed to talk to her right away Mary looked nervous officer Kirk could tell
00:35:51
something was bothering her as he continued to press her for information Mary began to
00:35:59
cry I'm Jesse she said I've been using my daughter's name on the internet as Mary Sheila would later
00:36:11
explain in an interview with Wired Magazine she claimed to have signed up for an account on Pogo to play games as
00:36:18
a way of relaxing it was only after paying a fee for a premium service that she realized
00:36:24
she'd inadvertently used the Gest name and details and was therefore directed to the sight's room for
00:36:32
teenagers Mary said she was happily married to her husband and had no romantic feelings for anyone
00:36:38
else she'd only started talking to Tom Montgomery's Alter Ego of Tommy because Tommy seemed troubled and in need of
00:36:46
care Mary offered no explanation for why she'd sent him photos of her daughter wearing a bikini engaged in cyber sex
00:36:54
with him or agreed to marry him after learning from Cindy Montgomery that Tommy wasn't real Mary said she
00:37:03
became concerned that Montgomery might be talking to other young women online she therefore decided to keep
00:37:10
communicating with him as a way to distract him from other girls as his temper flared and he became
00:37:18
increasingly jealous Mary continued speaking to him out of fear he might harm himself or others if she
00:37:25
didn't Mary said she'd never had feelings for Brian Barrett either he was simply a sweet kid who started flirting
00:37:34
with her and she hadn't known what to do without exposing her true identity the investigators in New York
00:37:44
who had been communicating with the Jesse were stunned to learn about this Revelation Mary shiler had sounded just
00:37:52
like a teenage girl during their phone conversations one day detective was so disbelieving that he drove down to West
00:37:59
Virginia to meet Mary for himself there Mary Sheila's computer was confiscated by this point she had been
00:38:09
communicating with Tom Montgomery for roughly a year and a half on the computer investigators found
00:38:16
hundreds of images of Mary's daughter Jesse many which were clearly taken without Jesse's
00:38:23
knowledge some photos focused on particular body parts and were taken from behind in a video that Mary had clearly
00:38:31
filmed without her daughter's knowledge or consent she aimed the camera up at Jesse's
00:38:37
skirt she then sent the footage to several individuals asking do you like it it turned out that Mary had been
00:38:47
talking to more men than just Tom Montgomery and Brian Barrett she had sent photos of her
00:38:53
daughter and pairs of Jesse's underwear to multip M online admirers Jesse's Myspace page had
00:39:01
actually been a fake maintained by Mary investigators also gained access to the chat logs between her Tom Montgomery
00:39:10
and Brian Barrett hundreds and hundreds of pages documented the countless hours Mary had
00:39:17
spent talking with the two men Montgomery's messages made it clear how much he'd hated Brian Barrett for
00:39:24
becoming involved with the Jesse he'd made repeated threats against both Brian and Jesse's lives and it was clear
00:39:32
he fantasized about committing violent ax he talked about how he was a former Marine and knew how to assassinate
00:39:45
people investigators finally managed to track Tom Montgomery down he hadn't gone down to seek revenge
00:39:53
against Jesse after all but was still in the Buffalo area and showed up for a shift at Diner as
00:40:00
normal detectives visited him at work and asked if he could accompany them for questioning Montgomery agreed but asked
00:40:08
if he could go to his car to retrieve his lunch first he explained that he'd brought
00:40:14
peaches and didn't want them to spoil while left in the car detectives took note of this fully
00:40:21
aware that a peach pit had been found at the scene of Brian Barrett's murder [Music]
00:40:28
Tom Montgomery denied any involvement in the crime he said that on the night in question he'd gone out to eat at a local
00:40:36
restaurant he'd arrived home sometime between 10: p.m. and 10 at least 6 minutes before Brian was
00:40:44
killed Montgomery's wife refuted this saying he'd arrived home at least half an hour later than he
00:40:52
claimed cell phone records also confirmed that Montgomery was in the vicinity of Diner braid at this
00:41:00
time testing of the Peach Pit left next to Brian's truck was tested for DNA it came back a positive match for
00:41:09
Tom Montgomery a search warrant was obtained for the Montgomery family home on the
00:41:17
computer investigators recovered hundreds of pages of conversations between Jesse and Montgomery as well as
00:41:24
photos of Jesse lingerie that Mary Sheila had sent him while pretending to be Jesse was found stashed amongst
00:41:31
Montgomery's belongings investigators also noted that the Montgomery family had a pet dog with
00:41:39
fur that looked to match the dog hairs found on the gun clip recovered at the crime
00:41:45
scene Montgomery owned several Firearms but there was no M1 A1 rifle in his gun cabinet however investigators did find
00:41:55
an interesting picture in one of the family albums in one old photo of Cindy Montgomery the gun cabinet was visible
00:42:03
in the background and there it was in the photograph an M1 A1 rifle Montgomery's work items were also
00:42:15
seized tucked away in a toolbox investigators found a note that he'd scribbled on Diner braid
00:42:21
stationary it read on January 2 2006 Tom Montgomery 46 years old ceases to exist and is replaced by an
00:42:33
18-year-old battle scarred Marine he is moving to West Virginia to be with the love of his
00:42:42
life the note described how 18-year-old Tommy had a black belt in karate $2.5 million in the bank and looked like a
00:42:51
red-headed Harrison Ford it appeared to be some kind of attempt by Montgomery to manifest
00:42:58
himself into an entirely different [Music] person as detectives sat Tom Montgomery
00:43:09
down for an interview they revealed that the woman he' killed Brian Barett over wasn't who Montgomery thought she
00:43:16
was she was a woman around his age who had been posing as her 18-year-old daughter the blood drained from
00:43:25
Montgomery face it was obvious that he was completely shocked on November 27 2006 Tom
00:43:36
Montgomery was charged with the murder of Brian Barrett and held in remand in a recorded phone conversation
00:43:44
to his wife Cindy from jail Montgomery seemingly admitted that the gun clip found near Brian's truck was
00:43:52
his he explained that the case had been covered in their dogs fur because his car was
00:43:58
filthy yet he also maintained that he hadn't killed Brian according to Montgomery Brian had
00:44:06
been receiving phone calls at work from people who disliked him and he believed one of these individuals must be
00:44:14
responsible Montgomery claimed he didn't mind when Jesse became involved with Brian he was just happy that she'd found
00:44:21
someone closer to her own age as Montgomery's trial date loomed both Cindy and the couple's daughters cut all
00:44:32
ties with him Montgomery attempted to take his own life as a result and his weight
00:44:39
plummeted eventually he agreed to plead guilty to first-degree manslaughter wanting to spare his daughters from the
00:44:45
ordeal of a criminal trial during sentencing the judge described the crime as quote a totally sens killing the result
00:44:57
of a non-existent relationship a love triangle between three people who did not even know each
00:45:05
other Tom Montgomery was sentenced to 20 years in prison making him eligible for
00:45:11
parole in 2024 at the age of 65 in 2009 director Barbara Schroeder made a documentary about Brian Barrett's
00:45:23
Murder She called the film tall hot blonde after Mary Sheila's online username during an interview for the
00:45:32
documentary Tom Montgomery didn't Express remorse for Brian's murder or even discussed the crime
00:45:38
directly instead he focused on his State of Mind at the time and his relationship
00:45:44
with Jesse Montgomery said he never doubted that Jesse was anyone other than who she
00:45:51
said she was this was partly because of the enormous number of photographs Mary Sheila had sent of her
00:45:59
daughter Montgomery believes his problem stemmed from seeking Solus online instead of talking to his family about
00:46:07
his issues Rex Bieber a clinical psychologist who appears in the documentary has speculated that a part
00:46:15
of Tom Montgomery truly believed in his Fantasy Life as Tommy this was evidenced by the note he
00:46:22
wrote to himself about his imagined transformation into the 18-year-old Marine when that fantasy was shattered
00:46:30
Montgomery saw himself as victimized in an interview with The Daily Beast Rex bber
00:46:38
stated by breaking the fantasy and his ability to live in it Mary was killing any hope he had to save himself from a
00:46:47
psychological perspective she engaged in cyber homicide Mary shiler also spoke to Barbara
00:47:00
Schroeder but refused to be filmed or recorded she told Barbara that all she ever wanted was to be a good
00:47:07
mother after her children grew up she became bored and lonely leading her to seek Company
00:47:14
online she maintained that she'd only spoken to Tom Montgomery to prevent him from talking to real
00:47:21
teenagers Mary intended to write a book about the dangers of the internet Mary never apologized to her
00:47:30
daughter Jesse or acknowledged that she'd done anything wrong she never told her family about
00:47:36
what she'd been doing not even after police came to speak with her about Brian Barrett's
00:47:42
murder when she had to fly to New York to testify in front of Tom Montgomery's grand jury she finally told her husband
00:47:50
that she'd done something bad she said she'd been chatting online to two different men who worked together
00:47:57
and one had become jealous and killed the other Mary insisted there was nothing sexual or romantic to these
00:48:06
conversations it had just been chitchat about online games and the weather the truth came out when some of
00:48:15
Jesse's friends heard about the case and Jesse decided to Google her mother's name the search returned news stories
00:48:22
about Brian Barrett's murder roughly 400 mil miles away in Upstate New York Jesse was horrified to discover
00:48:31
exactly what had happened and how her mother had used her identity not only had Jesse's photos
00:48:38
been shared with numerous men they were also splashed all over the internet in coverage of the
00:48:44
case Jesse told her father who was equally distraught he divorced Mary and Jesse
00:48:52
cut off all communication with her mother despite Mary Sheila's actions she didn't
00:48:59
technically commit any crimes and therefore cannot be charged in relation to Brian's
00:49:05
murder Tom Montgomery feels that Mary should be incarcerated for the role she played as du Brian Barrett's
00:49:13
parents the barretts have also advocated for laws requiring greater accountability
00:49:19
online they remember their son as being shy and quiet despite his tall stature athletic
00:49:27
build at the time of his death Brian was gaining confidence and discovering who he wanted to
00:49:33
be on weekends he spent his time volunteering as a coach for a little league baseball
00:49:40
team Brian loved working with kids so much that he decided to become an industrial arts teacher teaching
00:49:47
students to work with the wood and medal Brian's father Daniel has occasionally blamed himself for his
00:49:56
son's death it was Daniel who had found the advertisement for the job at Diner and encouraged his son to
00:50:04
apply Daniel also worked in it and was the reason the family had a computer and the internet at
00:50:12
home but ultimately the barretts know that those responsible for Brian's murder are the two middle-aged
00:50:19
individuals who took their fantasies too far they believe that what might have saved their son was
00:50:28
communication if Mary Sheila or their son's co-workers had reported Tom Montgomery's death threats then Brian
00:50:36
might still be alive [Music] [Music] today

Badges

This episode stands out for the following:

  • 90
    Most shocking
  • 90
    Biggest twist
  • 85
    Most heartbreaking
  • 85
    Most surprising

Episode Highlights

  • The Truth Unveiled
    Cindy Montgomery reveals to Jesse that Tommy is actually her husband Tom, a 46-year-old man.
    “You need to be much more cautious with your safety.”
    @ 12m 00s
    November 11, 2023
  • A Toxic Relationship
    Jesse and Montgomery's relationship devolves into a toxic cycle of jealousy and threats.
    “I am the Ultimate Weapon, I am a marine.”
    @ 23m 53s
    November 11, 2023
  • Mary's Deception Unveiled
    Mary Sheila's use of her daughter's identity leads to shocking revelations and consequences.
    “I've been using my daughter's name on the internet.”
    @ 36m 03s
    November 11, 2023
  • The Online Love Triangle
    A bizarre love triangle involving Tom Montgomery, Brian Barrett, and Jesse escalates dangerously.
    “This was a totally senseless killing.”
    @ 44m 53s
    November 11, 2023
  • Brian's Passion for Teaching
    Brian dedicated his weekends to coaching little league baseball, inspiring young minds.
    “Brian loved working with kids so much that he decided to become an industrial arts teacher.”
    @ 49m 40s
    November 11, 2023
  • A Father's Regret
    Daniel Barrett occasionally blames himself for his son's death, reflecting on missed warnings.
    “They believe that what might have saved their son was communication.”
    @ 50m 22s
    November 11, 2023

Episode Quotes

  • I know you're being careful honey, but anything can happen.
    An online love triangle leads to a deadly crime
  • If he existed, I would still be holding him every night.
    An online love triangle leads to a deadly crime
  • I still feel Tommy in my heart.
    An online love triangle leads to a deadly crime
  • I'm asking you to love me enough to let me go.
    An online love triangle leads to a deadly crime
  • A totally senseless killing.
    An online love triangle leads to a deadly crime
  • They believe that what might have saved their son was communication.
    An online love triangle leads to a deadly crime

Key Moments

  • Online Gaming00:39
  • False Identity01:08
  • Love and Betrayal21:45
  • Veiled Threats25:06
  • Police Involvement34:27
  • Trial and Sentencing44:42
  • Documentary Release45:21
  • Coaching Kids49:36

Words per Minute Over Time

Vibes Breakdown