Web's Killer Love Triangle

Talhotblond, a documentary released on DVD this week, tells the story of a chat-room flirtation that left one man dead, another imprisoned, and three families torn to shreds.

Thomas Montgomery, 46, a machinist, Sunday School teacher, and former Marine from Clarence, New York, received a message in a gaming site chat room in spring 2005 from someone with the handle "talhotblond," who informed him that he was in the kids section. Concerned about the appearance of an older man mingling online with minors, Montgomery told talhotblond that he was on his father's account–and that he was really a buff, 18-year-old Marine named Tommy.

The documentary talhotblond, directed by journalist Barbara Schroeder, was released this week on DVD, and tells the remarkable year-and-a-half-long saga of infatuation, deceit, and violence that followed, leaving one man dead, another imprisoned, and three families torn to shreds.

"He was clearly vulnerable, clearly a little off," said Schroeder. "For the entire year and a half they communicated, he exhibited rage issues, and she continued to egg him on."

Montgomery, using the handle "marinesniper," sent talhotblond–a lithe, fresh-faced 18-year-old West Virginia girl named Jessi–a 30-year-old picture of himself in military dress. The pair then seduced each other for months, as "Tommy" shared tales of combat in Fallujah, which Montgomery learned about by watching the news, while Jessi sent sizzling bikini photos and a split heart pendent that said "Jessi and Tommy forever." There was even serious talk of marriage.

At one point, Montgomery wrote a bizarre note to himself that read, in part, "On January 2nd, 2006, Tom Montgomery (46 years old) ceases to exist and is replaced by a 18 year old battle scarred marine…" The note went on to say that this new 18-year-old resembled a red-headed Harrison Ford, and had $2.5 million in the bank and a 9-inch penis.

But then the fantasy, which Montgomery later described as "a drug," hit a snag. Montgomery's wife, Cindy, found a package Jessi had sent to Tommy, and Cindy mailed Jessi a letter with their family photo, explaining that her "Tommy" didn't exist, and showing her that the real Tommy was a balding middle-aged pudgeball with two kids.

The heartbroken Jessi sought revenge by befriending, in the same chat room, a 22-year-old co-worker of Montgomery's named Brian Barrett (IM handle: beefcake), for whom Montgomery had been a mentor. Jessi flirted with Barrett, whom she goaded into humiliating Montgomery at work and online. Passions intensified, and Montgomery began making threats against both Barrett and Jessi's mother.

Schroeder includes several of the thousands of IMs that revealed the love, lust and scorn among the three in her film. At one point, Montgomery told Jessi that Barrett had "made a very deadly enemy," and that by continuing contact with him, "u have done what I feared most...turned my heart ice cold." He also wrote that "brian will pay in blood."

Jessi, meanwhile, seemed to feed off Montgomery's aggression.

"He was clearly vulnerable, clearly a little off," said Schroeder. "For the entire year and a half they communicated, he exhibited rage issues, and she continued to egg him on."

While Jessi and Montgomery engaged in a creepy erotic relationship online, with the machinist typing to his barely legal cybertoy how he'd "slide all the snake slowly into his lady," Jessi continued playing Barrett against Montgomery. One night, in a jealous rage, Montgomery fired three fatal bullets into Barrett, killing him, in their factory parking lot.

Throughout all this, neither Barrett nor Montgomery ever actually met the object of their mutual desire.

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While a fatal feud for a mystery woman seems remarkable, Rex Beaber, a clinical psychologist and attorney who's quoted in the film, notes that the Jessi/Montgomery relationship could only have prospered as fantasy–and that breaking that fantasy made tragedy almost inevitable.

"When word got out about the sniper identity not being real, what [Jessi] did from Montgomery's point of view was a kind of homicide," Beaber told The Daily Beast. "By breaking the fantasy and his ability to live in it, she was killing any hope he had to save himself. That's why his impulse toward her was murderous–from a psychological perspective, she engaged in cyber homicide."

Co-workers led the police to Montgomery. Investigators then learned of Jessi through his computer, and dispatched officers to her Oak Hill, West Virginia home to make sure she was safe. Once there, a policeman asked Jessi's mother, Mary Shieler, where Jessi was. Shieler hemmed and hawed, and began to cry. Then she made a startling confession.

Her daughter had never communicated with either of the men. It was her–dumpy 45-year-old housewife Mary Shieler–who used sexy photos of her own daughter to seduce both men, including having cybersex with them using her daughter's name and image, and eventually driving one to murder the other.

It was later learned that Shieler had flirted online, as Jessi, with other men as well, even once having pointed a videocamera up her daughter's skirt for a video she sent to several men with the question, "guys, do you like it?"

While talhotblond features excerpts of a prison interview with Montgomery, Shieler refused to be interviewed, although Schroeder spoke to her for twenty minutes off-camera.

Shieler, according to Schroeder, has never apologized to her daughter, shown any remorse, or acknowledged wrongdoing of any sort.

"She [said she] felt like she was doing [Montgomery] a favor," said Schroeder. "I said, 'But why did you keep talking to him, because he threatened you,' and she said, 'I was afraid if I didn't talk to him, he would talk to real teenagers.' I just thought, oh god."

Montgomery pled guilty to first degree manslaughter and was sentenced to 20 years, although he's now appealing, claiming that his plea was coerced. While Mary Shieler's husband divorced her and Jessi cut off contact (Shieler approached Jessi at the divorce hearing, according to Schroeder, and said, "why don't you get over this?"), there has been no legal recourse to try Shieler, who has said she plans to write a book about the dangers of the Internet.

Brian Barrett's parents started a petition to enact laws to protect against future Mary Shielers. But there's no clear indication of what such laws would look like. In 2008, Missouri mother Lori Drew was initially convicted of three misdemeanor counts of computer fraud for posing as a teenage boy to send harsh messages, including one that said "the world would be a better place without you," to a 13-year-old girl named Megan Meier, who then committed suicide. Given that there were no specific laws to address what Drew had done, prosecutors based their case on Drew having violated MySpace's terms of service. But that verdict was overturned in 2009 by a federal judge, who said that the verdict "criminalizes what would be a breach of contract."

"It's rare that a new law is the solution to social problems," said Beaber, who suggested specific injunctions from "being deceptive on the Internet," similar to orders of protection, as a possible solution.

"Maybe more people have to get killed before people pay attention to this problem," said Schroeder. "Something like this will happen again. Free speech is one thing, but when you use it as a drug and a weapon, we need laws for that."

The final irony to this case and talhotblond is that behind the well-matched youthful sizzle of the Jessi and Tommy personas lay another, equally well-matched pair: the two malcontented strangers who created them. Montgomery and Shieler were both lonely people who reached their mid-forties with their best days behind them, who then created deadly deceptions in the hopes of recapturing the glory of youth, and of finding real intimacy by fervently denying their true selves.

Had they ever met in real life, Thomas Montgomery and Mary Shieler might just have been the perfect couple.

Plus: Check out more of the latest entertainment, fashion, and culture coverage on Sexy Beast—photos, videos, features, and Tweets.

Larry Getlen is a regular contributor to the New York Post, and has also written for Radar, Maxim, Variety, and Esquire. Follow him on Twitter.