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A Journalist on the Inside Upends Good vs. Evil Criminal Stereotypes

September 23, 2025
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A Journalist on the Inside Upends Good vs. Evil Criminal Stereotypes
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THE TRAGEDY OF TRUE CRIME: Four Guilty Men and the Stories That Define Us, by John J. Lennon


America’s true-crime obsession is so inescapable, John J. Lennon writes in “The Tragedy of True Crime,” that even in prison, everything is filtered through its lens. Prisoners learn about one another’s crimes by watching episodes of “Dateline” and “48 Hours.”

Lennon, who is incarcerated himself, tells the story of when his then-wife came to see him at Sing Sing in 2018. In the visitation room, she spotted a man she immediately recognized from an episode of “20/20,” who had been convicted of orchestrating his wife’s murder. She couldn’t turn away. “His eyes are so blue,” she marveled.

“The Tragedy of True Crime,” Lennon’s impressive first book, combines personal history with profiles of other men with whom he has done time. Currently serving the 24th year of a 28-years-to-life sentence for murder, drug sales and gun possession, Lennon has spent the past decade developing a successful career as a jailhouse journalist. Here, he writes with rare authority about prison and the uneasy space where journalism meets entertainment. He recounts his experience watching an episode of “Inside Evil With Chris Cuomo,” in which his own crime was re-enacted in slow motion, a faceless stand-in for his 24-year-old self pulling the trigger. The lurid scene — moody lighting, somber voice-over — replayed again and again.

Proud of the more reflective man he’d become in midlife, and of the recognition his prison reporting had earned him, Lennon had agreed to be interviewed. But when the camera cut to his victim’s sister, visibly anguished, he understood, too late, what the show was really after. “I watched her cry on the television inside my cell, still carrying the pain I caused her,” he writes. “Why were we reliving the trauma — so personal, so private — on a true-crime television show?”

Lennon’s ambition is not to turn human suffering into spectacle, but to restore complexity to his own story and those of the men around him. “The good-versus-evil binary is lazy storytelling,” he writes. “It’s also an inaccurate depiction of why violence occurs.”

He threads an account of his troubled early life and how he came to shoot a man in Brooklyn in 2001 into his reporting on three other men, each of whom has committed a shocking crime. There’s Robert Chambers — dubbed “the Preppy Killer” by New York tabloids after he strangled a fellow teenager, Jennifer Levin, in Central Park in 1986 — whom Lennon met while Chambers was serving time on a subsequent drug charge. There’s Milton E. Jones, who, at 17, took part in the fatal stabbings of two Buffalo priests in 1987. And, finally, there’s Michael Shane Hale, who kidnapped and dismembered his Brooklyn lover in 1995. (Hale’s crime, another prisoner tells Lennon, is like “some [expletive] you’d see on ‘Snapped.’”)

Though each man has faced intense media scrutiny, Lennon demonstrates with his own reporting just how superficial that coverage has been, and how it has done more to obscure than illuminate. His richest portrait is of Hale, whom he shows stripped of sensationalism. Lennon traces the path from Hale’s earliest years as a love-starved child in Kentucky who endures physical and sexual abuse to his time as an unmoored young man in New York City, trading sex for money, to the moment when, at 23, he was so overcome by rage at his controlling and abusive lover that he smashed the man’s head against the ground again and again. Lennon describes Hale laying a plastic bag over his victim’s face. “I, too, covered the face of the man I killed,” he writes. “I didn’t want to see what I’d done.”

Lennon does not absolve or sanitize. He does not soft-pedal the violence that he and his subjects carried out, or offer satisfying answers when there are none. Instead, he shows the middle-aged men he and his subjects have become, their volatility tempered decades after their crimes. Hale, in his 50s, works as a re-entry facilitator, preparing men to leave the prison where he will most likely spend the rest of his life. Jones, though gripped by mental illness, pursues a master’s degree in theology.

Their evolutions take place outside public view. Most true-crime narratives end with a punishment being handed down. But, Lennon writes, “that’s only half the story. I contend that the lives lived in prison after a crime are just as fascinating, and important, as those that were spiraling before it.”

Lennon’s proximity to his subjects leads to some astonishing moments, including a scene he relates of Chambers’s efforts to connect with some of the prison’s most marginalized occupants. “I’d see him from the mezzanine view of my cell on the second tier as he talked with the hearing-impaired men in the cellblock, signing with his hands in the air, his face expressive and sincere,” Lennon writes.

I’ll confess that I balked at the suggestion that there was a tender side to Chambers (who was released on parole in 2023). Having also been a teen in 1980s New York, I could not let go of my certainty that he was the embodiment of casual cruelty and remorselessness — a satisfyingly two-dimensional villain. Did I really have to consider his humanity? But Lennon, who reserves some of his toughest questions for Chambers, is not asking us to render final moral verdicts on these men, but rather to sit with their complexity and contradictions.


THE TRAGEDY OF TRUE CRIME: Four Guilty Men and the Stories That Define Us | By John J. Lennon | Celadon | 356 pp. | $29.99

Pamela Colloff writes about the American criminal justice system for ProPublica and The New York Times Magazine.

The post A Journalist on the Inside Upends Good vs. Evil Criminal Stereotypes appeared first on New York Times.

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