Fake Teens VI: Online Teens

One of the following two stories ends in tragedy. The other ends somewhat happily for everyone. But both shine a bright light into the depths of online deception. I see these cases not so much as suspense thrillers (like the documentaries made about them), nor cautionary tales (as the media presents them), but as reminders of just how far a few people will go for attention.


Four years ago, two families and two innocent young people fell victim to the fantasy lives of two incredibly manipulative, unbalanced chat addicts.

In 2002, college student Brian Barrett began working at the Dynabrade factory in Clarence, New York, to help pay his tuition. A quiet and good-natured former athlete with wholesome good looks, the 18-year-old wanted to become a shop teacher. By 2006 he was studying industrial arts at Buffalo State.
Brian had an unlikely friendship with one of his co-workers, 45-year-old former Marine Thomas Montgomery. Tom had left the Marines as a young man with a drinking problem. When Brian Barrett met him, though, Tom was a dry, thoroughly reliable family man who taught Sunday school, volunteered on his daughters’ swim team, and had not so much as a speeding ticket on his record. He found his work as a machinist monotonous and uninspiring, but the pay was decent.
The only problem in Tom’s life was that he felt disappointed in himself, and craved more adventure. He started gambling and gaming online, and in mid-2005 he began chatting with a 17-year-old girl from West Virginia who called herself “Talhotblond” [sic]. Jessi sent him a few sexy photos of herself, and she was indeed tall, hot, and blond – perfect in every way.
Tom, who called himself “Marinesniper“, sent Jessi a 30-year-old photo of himself in uniform and told her he was 18-year-old “Tommy”, heading off to boot camp.

Jessi was an intriguing blend of woman and girl. She was an outrageous flirt and sent “Tommy” slideshows of herself posing provocatively in miniskirts and bikinis, but she lived with her parents and brother in the little town of Oakhill, West Virginia, where she played softball and basketball.
She and Tommy had cybersex and talked to each other on the phone daily.
Tom quickly fell in love. Not only with Jessi, but with his own online persona. He had given Tommy the Marine a chequered backstory: He hadn’t felt real love since his mother’s untimely death, and became a Marine to assuage his guilt over raping a girl when he was younger. Sometimes he felt suicidal.
Letters Tom Morgan wrote to himself in early 2006 indicate he was fantasizing about becoming the “good looking, battle hardened” Tommy, with a fake birth certificate and Social Security Number. Tommy would look like a redheaded Harrison Ford, sport a 9-inch penis, and have $2.5 million in the bank. He would have a black belt in karate.
Jessi called him her “sweet, sexy Marine”. On Christmas Day 2005, just six months after they met online, Tommy told her he was shipping off to Iraq and asked her to marry him on his return. She said yes.

Bizarrely, Tom also pretended to be “Tom Senior”, Tommy’s military dad. He chatted with Jessie online when his son was unavailable in Iraq, and shipped Jessi’s snail mail to him via “military contacts”.
When Tommy flipped out over Jessi flirting with other guys online, Tom Sr. was angry with her too, because his son really cared for her and would believe her “lying ass”. He remained angry with Jessi long after his “son” forgave her.

When Tommy, facing death in Iraq, lapsed into suicidal depression, Jessi coaxed him out of it.

By the summer of 2006, the guilt was getting to Tom Montgomery. He had an anxiety attack that he mistook for a heart attack. He tried to stay offline, but that made him even more anxious.
His wife of 17 years, Cindy, had been suspicious for a while, asking questions about who Tom was chatting with for hours. He gave her vague, reassuring answers that comforted neither of them.
Then Cindy discovered one of Jessi’s photos, sent by mail along with a pair of panties, and the jig was up. She was deeply weirded out that her husband was posing as a soldier (and a soldier’s dad) to seduce a girl not much older than their daughters.
She fired off a letter to the girl, explaining that “Tommy” was a 46-year-old married man. She warned Jessi to be more cautious online so she wouldn’t again be hurt by someone who had “mastered the art of manipulation and lies”. She enclosed a Montgomery family photo.

Jessi was just as shocked and wounded as Cindy. She demanded to know why Tom had deceived her. Incredibly, though, their relationship didn’t end. Jessi either wanted to learn more about the real Tom, or she wanted to get even: She turned to one of Tom’s online friends – Brian Barrett (“beefcake”). Soon, she began sending Brian photos of herself and calling him “Sexy”, an instant replay of her romance with Tommy. They fell in love, sort of.
Jessi threw her new “relationship” with his young coworker in Tom’s face, praising Brian’s honesty. Of course he realized she was trying to make him jealous, but as soon as she re-initiated contact, Tom knew he wanted her back. He apologized for his lies again and again, pleading for a second chance.

On the surface, Brian and Jessi were a good match. They both loved playing sports, and he was just a few years older than she was. Best of all, Brian wasn’t a middle-aged dad posing as a suicidal teenager. But Jessi craved drama and risk, just like Tom. She finally agreed to resume her relationship with Tom, on one condition: He had to continue pretending he was the 18-year-old Marine she had agreed to marry. “Don’t let Tommy die,” she begged him. At first, Tom refused. That’s when Jessi and Brian began taunting him in the online game chats, calling him a loser and a predator. The harassment amused Brian for a while, but then he began to feel Jessi was taking it too far. He could see a vindictive, manipulative side to her that didn’t appeal to him at all.

By this time, of course, the camaraderie between Tom and Brian was at an end. Brian was creeped out by Tom’s pursuit of a girl young enough to be his daughter, and Tom was extraordinarily bitter that Brian had chosen Jessi over their friendship. More than that, he was threatened. How could he possibly compete with a single guy in his early twenties? He was anchored to a home and family, while Brian could do pretty much as he pleased.
This hit home hard when Brian accepted Jessi’s invitation to visit her in West Virginia. Tom wrote to him, “tell ur little whore to stay the fuck out of my life.”
Before Brian packed his bags, however, Jessi broke it off. She accused him of only being interested in sex. She drifted back to Tom and tried to woo him, but he was still furious with her. “You mean shit to me these days,” he wrote.
She was finally able to melt him somewhat by writing, “U and only U are my connection to Tommy and I will love him till I die.”
Their renewed friendship was an uneasy one, clouded by Tom’s overwhelming hatred for Brian. In one chilling exchange, Tom claimed he had come very close to actually murdering Brian.

Tom: “I hate him with a passion and for 10 cents I would eliminate him.”
Jessi: “that’s a little drastic isn’t it”
Tom: “payback is a motherfucker, Jessi. I am the ultimate weapon. I am a Marine.”
Jessi: “what are u going to do?”
Tom: “Let’s just say ur piece of shit boyfriend came with a hair of dying… the day after U 2 assholes told me you were fucking with me… had I pulled a little harder he would gone… Brian will pay in blood.”

Now for the average person, declarations like “he will pay in blood” would be alarm bells. Not for Jessi. Tom’s fury and threats of homicide only drew her closer to him. She pledged never to betray him again, and began having cybersex with “Tommy” again.
But Jessi’s promises didn’t last long. Very soon, she was flirting with other guys on the online chats right under Tom’s nose.
Finally, Tom had enough. He ordered Jessi to leave him alone, or he’d physically harm her and her mother. (Earlier, he had threatened to post Jessi’s home address online so “the niggers can find you”.) This is when Jessi’s mom appeared online for the first time. She told Tom to keep away from her daughter. He agreed.
Two weeks later, Jessi was back in his life. “I have totally defied my ma to be with you,” she wrote.

While renewing her ties with Tom, Jessi began writing to Brian again, too. Tom discovered this through Myspace and was enraged. He wrote to her, “U will pay now bitch. U better be very afraid now. I told u what would happen if u and Brian got together.”

Jessi informed Brian that Tom was furious with both of them, and that’s as far as it went. Authorities weren’t notified about the repeated threats against Brian, Jessi, and Jessi’s mother at any time. Privately, though, Jessi and Brian expressed concern about Tom’s anger. Brian mentioned that Tom had tried to hit him with his car in the Dynabrade parking lot.

Jessi: “Brian I am really afraid of him.”
Brian: “Yea me too he’s crazy”

On September 15, 2006, Tom phoned Jessi to scream in an incoherent rage. She hung up on him.

That night, Brian finished work around 10:00 PM and headed out to his truck. When he was in the driver’s seat, Tom snuck up on him from behind and fired three shots from a .38-calibre rifle through the window. Because it was a Friday, Brian’s body remained undiscovered for two days.

When police learned about the sick love triangle and couldn’t locate Tom Montgomery, they feared the worst: He could be on his way to West Virginia to harm Jessi. Erie County Lieutenant Ron Kenyon phoned the girl immediately, informing her of Brian’s death and warning her to be cautious. Then he dispatched West Virginia police to her home.When Officer J. L. Kirk and a partner arrived at the little white house in Oakhill, Jessi’s mother answered the door. Mary Shieler already knew about Brian’s murder and seemed distressed about the situation, yet claimed her daughter wasn’t home.
“She was just here,” Kirk pointed out.
Something about Shieler’s attitude triggered his suspicion. After some fruitless back-and-forth, he asked her bluntly if she was “Jessi”.
The woman explained she did have a teen daughter named Jessi, who really wasn’t at home. But, yes, she was the Jessi known to Tom Montgomery and Brian Barrett.
Later, Mary would claim she never had any intention of disrupting her “happy” marriage for either of these men. With her kids nearly grown and Tim at work, she was lonely and bored. She cast herself in something like a heroic role, telling reporters she played along with Montgomery merely to keep him away from actual teen girls. And Brian Barrett? Well, he just got caught in the middle.

Mary Shieler was a 45-year-old housewife, known in her community as a devoted wife and mom. She went to all of Jessi’s games and volunteered at her daughter’s school. Mother and daughter were reportedly quite close, shopping and getting manicures together. Mary was clearly very proud of her lovely daughter, and spared no expense when it came to Jessi.
No one knew that the photos she continuously took of Jessi were being distributed to strangers over the Internet. Her husband, Tim, was mortified when he learned what she had done. He quickly filed for divorce.
Jessi was equally appalled. Mary never apologized to her, nor attempted to explain her actions. Jessi severed all ties with her mother.

Tom Montgomery, as it turned out, didn’t head for West Virginia. He remained at home, and on September 18 was taken in for questioning by Erie County Sheriff’s Deputy Jason Weiss and Detective Charles Tirone. He was shocked and upset to learn that his beloved, virginal Jessi was really a 45-year-old mother of two.
Tom said he took his two daughters, 12 and 14, out to dinner on the night Brian was murdered, and returned home at 10:15. His daughters supported his alibi, but Lisa Montgomery stated Tom arrived home around 11:00. That left plenty of time for Tom to go to the plant in Clarence and shoot his rival.
Worse yet, Tom’s cell phone records placed him near the plant around 10:00.
He denied owning a .38 rifle, even though a photo of it was discovered in his home along with a .38 handbook.
His DNA was found on a peach pit left near Barrett’s vehicle. He had purchased a bag of peaches shortly before the murder.

Charged with Brian’s murder on September 27, Montgomery pled not guilty. Initially, he said Brian had several other enemies who made threatening phone calls to him at work.
But he had no real defense other than the word of his two young daughters. In July 2007, he took a plea deal: 20 years for manslaughter.
He attempted to change his plea again at his sentencing.

Brian Barrett’s parents, Dan and Deb Barrett, filed a wrongful death lawsuit against Montgomery, Shieler, and Dynabrade. After the suit was dismissed, they campaigned for the development of “Internet accountability laws”.

In 2009 the documentary TalHotBlond, produced and directed by reporter Barbara Schroeder, aired on MSNBC. The instant message excerpts above were taken from that film.
Some of the more disturbing details were left out of the film, including Montgomery’s impersonation of “Tom Senior”, Montgomery’s racist threat to Jessi, and “Tommy’s” confession of raping a cheerleader.

Other Sources:

– “An IM Infatuation Turned to Romance, Then the Truth Came Out” by Nadya Labi. (Wired issue 15.09)
– “Thomas Montgomery: Bizarre Love Triangle” by Kristal Hawkins (TruTV.com Crime Library)

Online Teens Part II

Spoiler warning: Part II of this post contain complete spoilers for the film Catfish.

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