The freelance writer of Sing Sing

August 17, 2018
John J. Lennon, a journalist and inmate at Sing Sing Correctional Facility in Ossining, New York in January 2018. Photo: Karsten Moran for The Marshall Project

When John J. Lennon writes about the criminal justice system, he must first tell his own story. Lennon is Inmate No. 04A0823 in the New York State Department of Corrections, serving 28 years to life for murder and selling drugs. He has been on Rikers Island, in Clinton Dannemora, Green Haven, Attica, and now Sing Sing. He has battled addiction to drugs, smuggled in by fellow inmates, and painkillers, doled out by his jailors. He has spent time in solitary confinement. One afternoon, in a prison yard, he was stabbed in the chest with a shiv and left for dead with a punctured lung. But lately, he has found, his incarceration has given him unparalleled admittance to an always-hot topic in American media. “Who can beat my access?” he says. “I live around an orgy of story.”

Lennon is 41, with a thick chest, tattooed biceps, close-cropped black hair, and blue eyes. For the past five years, he’s worked as a freelance journalist whose pieces have been featured in The Atlantic, The New York Times, Pacific Standard, Esquire, and The Marshall Project. He has no computer and no direct access to the internet or email; he writes on a clear plastic Swintec typewriter. There are two phones on his floor, and Lennon is permitted to make calls only during certain hours of the day, to a pre-approved list of 15 numbers. Each call is prepaid collect (at his expense) and limited to 30 minutes. Prison libraries tend to have sparse collections, mostly law volumes and fantasy pulp, so for research—and to keep up with the literary world—Lennon subscribes to several magazines. He especially likes stories that weave first-person narrative into the reporting. “Whenever I used to read Esquire and GQ—the bang-bang, sexy, pop-your-collar magazines—I thought ‘I could do this shit,’” he says.

Lennon entered the prison system seventeen years ago, and he’s not eligible for parole until 2029. Until then, he has plenty of time to work.


NAMED AFTER HIS FATHER, Sean (Irish for John), whom he never knew, Lennon was raised in Brooklyn by Laura O’Connell, a single mother who ran a fleet of hot dog stands (all cash). They lived in the city’s housing projects. Her business flourished, which left plenty of money to send Lennon to the Malcolm Gordon School for Boys, a private school upstate. In seventh grade, he won second place in a writing contest for a piece of creative historical fiction about Benedict Arnold, as told by his cane. The prize was a $75 savings bond.

Later, O’Connell married a longshoreman, and Lennon loved hearing his stories about the Irish Westies mob, which commanded fear and respect among the working class in an older New York. When Lennon was 11, the family moved to Hell’s Kitchen, on the west side of midtown Manhattan, which in the eighties was a crime-ridden neighborhood; Lennon became more interested in being part of vandals’ tales than in telling them. After attacking a fellow student with a knife, he was expelled from the Malcolm Gordon School. He swiped his savings bond from his mom and cashed it to buy drugs. Soon, he found himself in and out of juvenile detention. At age 17, he was sent to Rikers Island on gun possession. “A white guy on Rikers in 1994?” he says. “That’s a pretty disgusting scene. I got my face punched in for a year. You’d think I’d have had enough after that. But no.”

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O’Connell, who had by then become a real estate agent, would snap freshly printed commission checks in her son’s face and ask him to come work for her when he was released. He refused. “I had plenty of opportunities, and I squandered them all,” Lennon recalls. “I went looking for this lifestyle and unfortunately I got everything it had to offer.”

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In 2001, Lennon was 24, back on the street, and deep in the drug game. He heard about a man who had been shaking down one of his dealers; Lennon decided that he needed to act to uphold his image. One night, he lured the man into a rental car and shot him several times with AR-15 semi-automatic rifle. Then he drove down to a pier and dumped the man’s body, and a couple of cinderblocks, into the bay. Less than a year later, Lennon was back at Rikers on other gang-related charges when the man’s corpse washed up on a beach in Brooklyn. After two jury trials—his mother hired a good attorney—he was convicted of murder.

In prison, Lennon continued his drug use. He was transferred from one maximum-security facility to the next. In 2008, when he was stabbed, it was by an acquaintance from Brooklyn making payback on the murder. Lennon’s lung collapsed; he couldn’t breathe. The guards were oblivious, and his fellow inmates walked the other way as he stumbled across the grounds toward the infirmary.

Later, as he recovered in bed, Lennon made a decision. He was disgusted with his life, and he wasn’t going to die behind bars—at least not without having done something meaningful first.

LENNON WAS TRANSFERRED to Attica, where he completed a 12-step program and enrolled in a creative writing workshop. The teacher, Doran Larson, was a literature professor at Hamilton College, in nearby Clinton. Larson assigned readings from anthologies like Best American Essays and The Art of the Personal Essay. He instructed the inmates in how to put their own stories to paper, and guided them through five or six drafts. From 2010 to 2012, Lennon made it to every session, about once a month, with several other regulars. “He was obviously very smart—cocky,” Larson recalls. He had a lot to learn, but he did have talent. “He had a natural sense of narrative structure,” Larson says. “A lot of people come in knowing what they want to write about, but not knowing how to put it together.”

Lennon had found an ideal mentor. “Larson showed me what good writing looked like,” he says. In class, he workshopped an essay arguing in favor of gun control based, uniquely, on his experience killing someone with an illegally purchased firearm. Satisfied with his work, he mailed it—with a one-page cover letter explaining who he was—to The Times and The Atlantic. “If you know John, he is not going to start at the bottom,” Leann Alspaugh, a friend and editor of the The Hedgehog Review, a literary journal, says. “He’s going to start at the top.”

A few days later, an envelope with “ATTICA CORREC FAC” stamped in red landed on the desk of David A. Graham, an Atlantic editor. The manuscript—an even-handed, almost clinical firsthand recounting of a grisly murder—held the American gun culture and political system to account while taking responsibility for his crime. Even more impressive, Graham recalls, were the clear voice and ease of storytelling:

My first gun was a chrome .25 caliber automatic with a pink, pearl handle. It was beautiful. But it was a killing machine, and at 14 years old I had the same hole in my heart that President Obama, in a Chicago speech, stated other child killers had. I had no business with that gun.

Graham was intrigued, though at a loss as to how to proceed. He checked out Lennon in the New York prisoner database, printed out an edit, and mailed the piece back. For the next few weeks, the two exchanged letters with edits and fact-checking fixes. Lennon tried to make up for any postal lag with extra diligence. “For a guy who’s been a loser his whole life, I’ve failed at the highest level,” says Lennon. “I blew all my opportunities. I was NOT going to blow this.” The piece, “A Convicted Murderer’s Case for Gun Control,” ran on the Atlantic’s website in August 2013. Nicholas Kristof picked it up for his blog, at The Times, and published another story by Lennon soon after. Lennon had started his professional writing career.


TO REALLY MAKE A NAME for himself in journalism, Lennon sensed, he was going to have to branch out beyond personal essays. In Attica’s law library, he studied policy to for op-eds he wanted to write about access to education and New York’s correctional system; the resulting pieces were published by The Times and Albany Times Union. He also tapped into his fellow inmates, like Lenny, a sexagenarian bank robber carrying a colostomy bag and facing his end in prison; Lenny became the subject of “Dying in Attica,” which ran in The Marshall Project.

Packing a pen wherever he went, Lennon found that being a reporter in a prison jumpsuit allowed him to cross otherwise impenetrable lines—of class, of race—that typical journalists couldn’t. He has steered clear of “innocent man” stories, however. As a confessed murderer, he thinks that he lacks the credibility to pull off reporting that exonerates. “When I’m writing about a guilty man, I’m writing about transformation,” he says. “I’m writing about a good man who did a bad thing. There’s ethos there. A guilty man has the better story. The innocent man is just fucked.”

As the scope and subject matter of Lennon’s work expanded, so too did his approach to doing this job from behind bars. All freelance writers try to network with editors and fellow writers, but Lennon has a rolodex of colleagues willing to do a little extra: Graham fields pitches for The Atlantic and helps direct ideas to other publications; Pete Davis, an editor from The Harvard Law Record, accepted a piece from Lennon and then volunteered to build him a website. Alspaugh, of The Hedgehog Review, published a piece about Lennon’s mother in 2016, and soon became a valuable sounding board as he developed other drafts—sending messages on his behalf, reaching out to editors and agents, looking up information online, and even taking dictation of manuscripts over the phone. “I kind of volunteered for it,” she says. “I have a fulltime job; I do most of it off company time. But to me, part of what I do is help writers. He’s a writer.”

Alspaugh set up Lennon with a book editor interested in publishing a memoir. He has also been in touch with a Hollywood producer, who has asked Lennon not only about his own story, but also about using him as a consultant and writer on documentaries to ensure authentic portrayals of life in prison. He wants to someday write for cable dramas and movies, too. “I see myself in a writers’ room telling my co-writers ‘Stop! That’s not how it is. That’s when people change the channel, when you write that corny shit,’” he says. “I want to be the voice to that gritty stuff. I think I’ll be able to be helpful in nailing the specifics and developing stories and characters.”

When Lennon began working on a piece about mental health care in American prisons, Alspaugh sent an early version to Eric Sullivan, an editor at Esquire. “Right off the bat, I knew that, by being incarcerated, he’d have a view of the prison world that any other reporter in the visitation room would not,” Sullivan says. “He had the ability to perceive the culture surrounding him and thoughtfully ingest it.” The first draft was about 5,000 words; Sullivan made notes in track changes and printed out the edit. By this time, Lennon had been transferred to Sing Sing, where prisoners can send as many letters of as many pages as they can afford to stamp, but they can receive only five pages per envelope. Sullivan took five pages at a time, folded them in thirds, stuffed them into a set of No. 10 envelopes, and sent them off.

Upon receiving Sullivan’s edits, Lennon sprawled out across his bunk, typewriter in his lap. If he needed information, he could look around his cell—he’d taped notecard-sized slips of paper, each containing a scene or quote from his reporting, in a patchwork outline across his walls. (If a fact he wanted wasn’t there, he’d have to wait to call someone to look it up.) His Swintec could only save up to 7,000 characters at a time, so he typed in two-to-four-page sections, aiming get them in shape before moving on. It was slow, tedious work. Sullivan, who was waiting the extra days and weeks for revisions, says that he came to see this as a benefit rather than a limitation—a rare editorial grateful response to a late draft. “That time between correspondence allows for thoughtful reflection,” he says.

Lennon added Sullivan to his call list, and would anxiously wait in line for the phone to check in. When the discussions dragged, Lennon would take down notes on requested edits while avoiding dirty looks from fellow inmates, waiting for their turn. Sullivan never knew when to expect a call, and when Lennon missed him, he’d call Alspaugh, who would type out an email. If he missed Alspaugh, he would call O’Connell, now living with Parkinson’s, to check Lennon’s inbox.

Slowly, the piece took shape. To complete the fact-checking process, Sullivan came to Sing Sing’s visitation room and taped an interview with Lennon, in which he verified his personal details from the piece.

The story, “This Place Is Crazy,” ran in the June 2018 issue of Esquire:

“What’s your diagnosis?” I asked.

“Schizoaffective disorder,” Joe said, a form of schizophrenia.

“Bugout” was the label Joe carried, just as “murderer” was mine. Here, where bugs were considered bottom-feeders, I wouldn’t want to switch places.

The byline not only helped raise Lennon’s profile in the journalism world, it also garnered him cred on the inside. “Most of my other stories ran online, and there’s no online in here,” says Lennon. “The Guardian? The Atlantic online? They don’t get the traction. Most inmates don’t get the prestige. But when you get published in Esquire—that’s delivered to every cell.”

So far, there have been no signs of retribution. “My friends all get scared when I go after the administration,” he says. “They’re like, ‘They put you in the box.’ There are pens in the box. There’s a better story in the box. That’s the last thing they should do.”

Instead, the guards seem impressed. Recently, a corrections officer held a copy of Esquire and playfully slapped the page.

“Yo, this is you?” the guard asked. “You wrote this?”

Lennon grinned.

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Correction: A previous version of this article said the Hedgehog Review article was published in 2014—it was published in 2016. It has also been corrected to clarify the guard slapped the magazine, not Lennon himself.

Tony Rehagen has written for Pacific Standard, GQ, Bloomberg, and ESPN The Magazine. He is based in St. Louis and is on Twitter @trehagen.