John J. Lennon was a privileged kid in New York, but something inside him couldn't resist the lure of the gangster lifestyle.

The walls were closing in on John J. Lennon — a drug deal gone bad, his own habit spiralling out of control and untrustworthy people everywhere he looked.

He sensed that he needed to take decisive action against the next person who crossed him.

When he realised his associate Alex was extorting one of his sellers in December 2001, Lennon lured him into a car on the streets of Brooklyn, New York.

Lennon, pictured around 1980 with his mother Laura O'Connell, left, and aunt Mary Ann, grew up in the projects of Brooklyn. Photo / Supplied
Lennon, pictured around 1980 with his mother Laura O'Connell, left, and aunt Mary Ann, grew up in the projects of Brooklyn. Photo / Supplied

He took an AR-15 out of the boot and shot his friend dead through the passenger window.

"I took his life, I shot him, several times," Lennon tells when we meet at the notorious Sing Sing prison, an hour out of the city up the Hudson River.

"And then I tried to get away with it, I tried to put him in an ocean, I tried to dispose of his body."

The 41-year-old, who is eloquent and confident throughout the interview, changes when he talks about his crime, um-ing and ah-ing, the room filling with long silences as his gaze flits from one spot on the floor to another.

"You know, it's difficult for me to talk about because I'm ashamed of that, I'm sorry that I hurt his family."

It's a crime he's had plenty of time to think about in the 17 years he's been behind bars, and he's not up for parole until 2029.

Lennon grew up in the projects and was just 11 when his father killed himself — but he had many advantages over some of friends, whose fathers had been jailed or murdered.

His mother, Laura O'Connell, was a "hustler" who made good money from a hotdog stand and got him into a prestigious boarding school — not far from the institution where he's now locked away.

"We lived in the projects butI was always the richest kid in the projects," Lennon says. "Everyone seemed to make it out all right but me, so there was a little something I had to be accountable for.

"I went looking for this lifestyle and even my friends acknowledged that, like, 'Yeah, you were a little much, you were dying to be like a gangster, like you really went looking for this life.' And I got everything that had to offer."


It was when Laura remarried and the family moved from Brooklyn to Hell's Kitchen, Manhattan, with its Irish mob origins, that Lennon's criminal career started to flourish.

The 41-year-old speaks several times of a "void" inside him. He was irresistibly attracted to the gangster culture woven through the fabric of his new neighbourhood.

Lennon was expelled from his private school at 14 and his mother — who now has Parkinson's and cannot visit — enrolled him in ninth grade at a city high school. He never went.

When he was 17, Lennon was caught carrying a gun, and spent a year in youth detention on the infamous Rikers Island, before "migrating back to Brooklyn", taking his new knowledge with him.

"I just sort of started sort of bringing my criminal mentality to that neighbourhood and eventually I started selling a lot of cocaine and heroin," he says.

"With drugs comes a lot of other things … people try to rob you, people try to get one over on you and with me, I already (was in) this void where I wanted to prove myself, and with the mystique of the lifestyle — as sick as it sounds — murder was something that was thought of as an accomplishment, and I know that's hard to hear, but that's how that lifestyle is."

Lennon didn't really have views on the drawbacks or merits of guns. "I was a criminal and I needed guns and I would buy them illegally," he says. "I've had 9mms, 45s, I've had tech nines, I've had several different guns."

As a young man, he was drawn to gangster culture and began dealing drugs and carrying a gun. Photo /
As a young man, he was drawn to gangster culture and began dealing drugs and carrying a gun. Photo /

While there are relatively strict laws on firearms in New York State, they were easy to obtain. Crack dealers who went down south to sell drugs would order white addicts with no record to buy guns, then bring them back to the city in the car boot, selling them on the black market at double the price — a process called "straw purchasing".

At the time he began considering murder, Lennon had been forced to throw away his last gun after another altercation in which he had shot at some people. "It was a chaotic time," he says. "I didn't hit anybody or kill anybody, it was just more of a situation."

The AR-15 "was the only gun that was available when I decided to kill Alex," he adds. "It wasn't like, 'give me the biggest gun', it was sort of convenient."


Lennon was sent down for 28 years to life, cycling through some of New York State's most mythologised prisons — Rikers again, Clinton Correctional Centre in Dannemora, Green Haven, Attica and today, Sing Sing.

In the early years, Lennon suppressed his dark thoughts with weed, heroin and cocaine, hardening even more as he observed vicious corrections officers pulverise fellow inmates and survived a revenge attack in which another prisoner stabbed him repeatedly in the side.

"It's almost a comfortable place when you rationalise, you know, 'That's what that lifestyle is, you get involved with that lifestyle, you either wind up dead or in prison'," he says. "That's a pretty straightforward narrative and, frankly, that's a narrative that helps you sleep at night.

"You come to prison and you talk to other guys and they want to know, what's your resume, like what did you do? And I — when I sort of show them the dopey clippings of the (New York) Daily News and the (New York) Post, the tabloids, whatever, 'White Boy Johnny', 'the killer', and all this kind of stuff, it's almost like an accomplishment, like, 'oh wow, yeah you're welcome, come hang out,' so it's an easy place to get lost in rationalisation, prison."

More than six years into his sentence at a series of maximum security prisons, Lennon began getting sober and facing up to the reality of what he did.

"It took me many years, yeah," he says. "Regret was what I felt at first.

"I got involved in a 12-step program and you start unpacking things like remorse, and amends, you start getting to those steps, doing an inventory, cleaning house, you start saying, 'Look', talking to your sponsor, 'What do I do with this, how do I get right with this?'

"It took me a while to get to remorse, that's not something that came to me right away."


Lennon had always had a talent for writing. In seventh grade, he won a $75 saving bond for his writing at private school — which he cashed and spent on drugs two years later.

At Attica, he took a creative writing course with a literature professor from a liberal arts college, and began spending time in his cell, tapping away on a clear plastic typewriter.

The notorious Sing Sing was home to many infamous criminals, and is where famous prison phrases originated. Photo /
The notorious Sing Sing was home to many infamous criminals, and is where famous prison phrases originated. Photo /

In 2013, his first article was published in The Atlantic — "A Convicted Murderer's Case for Gun Control". His writings have now appeared in the New York Times, Vice and New York Magazine.

Lennon began mailing typewritten pages or dictating to editors over the phone, after asking friends and family to connect him, as he does when we talk. Friends on the outside answer his emails.

Two years before his first piece was published, Lennon's brother Eugene died alone in a "quasi-rooming house" in 2011 after an opiate overdose. It was the smell that led them to him.

Like many inmates, Eugene was bipolar and a drug addict, bouncing in and out of jail. In June 2018, Lennon wrote about the "bugout" — prison speak for mentally ill inmates — in Esquire, and how 10 in every 11 psychiatric patients housed by the US government are behind bars.

"I would see some of these guys in prison and it would always remind me of my brother," he says.

Lennon has twice married and twice separated from women he met on a prison dating website. Inmates who are married are allowed conjugal visits — but making a relationship work has proved hard.

Today, Lennon rises before the loudspeakers and spends time reading, writing, working out and studying for a Bachelor's degree in behavioural science, the only one offered at the prison. His work has helped him to avoid the despair that grips many of his fellow inmates.

"I was always haunted by suicide, even when I saw the first person across from me hang himself in 2009," he says. "It was bizarre, he had just asked me for a cigarette and I was like man, maybe if I gave him a cigarette he wouldn't have hanged himself.

"I had a window in my cell in Attica and saw him playing football with these guys.

"It always rattles you … you see somebody before they do it, it's like, how did they go from playing football?

"It's this internal thing that's going on with someone and you really don't know, they really don't show it … It exemplifies the torture that goes on within."

Lennon and his mother in Attica, where he served time before moving to Sing Sing. Photo / Supplied
Lennon and his mother in Attica, where he served time before moving to Sing Sing. Photo / Supplied


When Lennon was first thrown in jail, he smuggled in weed, pills and heroin — "You name it, I did it."

The only substances not on the menu were cocaine and party drugs. "Those aren't big in prison, but you know the downers, that make you not feel, that's the thing to do in prison," he says.

"You gotta get the s**t out of your system. I came to prison, I did drugs, I sniffed dope, I smoked weed, I talked about people, that's the s**t you do, that's that prison s**t, you know, and some people just, you get stuck in that longer than others.

"I got stabbed up, I gave some, I took some, and then it's just like, enough of this already."

It's a journey many inmates take in jail, he explains. One friend is serving a 20-year sentence after a days-long cocaine and ecstasy binge ended with him picking up a gun to rob a store and killing the assistant behind the counter.

"The first time he touched a gun, he killed a man," says Lennon.

The friend, who was stabbed in the eye early in his incarceration, recently completed a degree in theology — a rare Master's program at a maximum-security prison. "For the next five years, he'll be doing nothing," says Lennon. "They've gotta walk down these huge sentences. There's some punishment that comes with prison that was not meted out by the judge."

When he arrived at Attica, it was known for dealing with the prison population with an iron first. "Beatdowns were all the time, you know, you'd be in your cell hearing screams through the hallways, just and it was very calculated, it was done almost sadistically," Lennon says.

"You suck your teeth at the wrong officer and they'll let the whole line file into the cellblock and then 'You, step out, get on the wall', and you know what's going down.

"It's a pretty sick scene … sometimes, you're going to hear screams.

"When prisoners would get assaulted, they would get charged with assault on staff, to justify the use of force … not only are you all bruised up, you're sent to solitary confinement."

In 2014, criminal justice non-profit the Marshall Project was launched, a New York Times article exposed the violence and thousands of cameras and microphones were installed. "The whole culture changed," says Lennon. "It was this prison with absolutely no oversight, and the guards could do whatever they wanted to instil their reign if you will, and now they were being watched by Big Brother."

The screams stopped, mostly.

The 41-year-old has come a long way, from a world of turmoil to Sing Sing — a prison known for its storied inmates and electric chair executions, but now one of the most progressive in the state.

"To thine own self be true," reads the Hamlet quotation inked on his arm, and it's an adage he lives by, despite the challenges of this tightly controlled environment.

It's beautiful outside this prison in Ossining, beside the village of Sleepy Hollow, all lush green trees and a dramatic vista of the wide, grey Hudson River, with the prison built right on the banks.

The electric chair in which Soviet spies Julius and Ethel Rosenberg were executed at Sing Sing prison in June 1953. Photo / News Corp Australia
The electric chair in which Soviet spies Julius and Ethel Rosenberg were executed at Sing Sing prison in June 1953. Photo / News Corp Australia

But the militant security at the gates, the intimidating watchtowers and Lennon's bowed head in prison greens as we walk in, are a reminder of what he did.

"It's something I'll always have to live with," he says of his crime. "That's the conflict of the writer, the murderer, that's the dichotomy that I will always grapple with."