Queer Life at Sing Sing Correctional Facility
I first read about Hale, who goes by his middle name Shane, in the new book, The Tragedy of True Crime: Four Guilty Men and the Stories That Define Us (2025), by prison journalist John J. Lennon. One of the featured men, Shane’s story leapt off the page with the aid of Lennon’s masterful prose as an example of someone whose gentle spirit shines through decades of near-constant adversity.
To say that Shane had a tough childhood in rural Kentucky in the 1970s and ‘80s is an understatement. He was molested by a friend of his father’s, viciously bullied at school, and chased out of the house by his mother with a butcher knife when she found his stash of Playgirl magazines. He moved in with his grandparents until the end of high school, when he enrolled in the Army.
As a young gay man in his early 20s — like so many LGBT people before him — Shane moved to New York City. Arriving with a suitcase and a lifetime’s worth of unprocessed trauma, Shane soon started dating Stefan, a client-turned-boyfriend almost 40 years his senior. Over the course of two and a half years, the relationship grew increasingly abusive. Stefan used his financial leverage as a method of manipulation. He socially isolated Shane, pimped him out, and sexually assaulted him.
Shane decided to return home to Kentucky, where Stefan soon tracked him down and convinced him to come back to New York. A month after his return to New York, Shane was ready to leave again. His situation was unlivable. Cops came and went. One October night in 1995, Stefan refused to let Shane pack his clothes. They got into a heated argument. Feeling backed into a corner with no way out, Shane killed his abuser.
He was sentenced to 50 years to life in a New York state prison in 1999, where he’s currently incarcerated. In the 30 years he’s been behind bars, Shane has learned a lot about himself. He’s had an awful lot of time to think, reflect, and introspect. His story in Lennon’s book can help us all better understand the complexities that can drive someone to commit a horrific crime.
Now in his 50s, I spoke with Shane over the phone about prison life, personal growth, and redemption.
In the early ‘80s, Shane grew up thinking he “was the only queer person in the world.” Today, by contrast, even gay, bi, and trans youth in deeply conservative or rural areas often have built-in community networks online. But Shane still remains cut off. At Sing Sing Correctional Facility, prisoners have no access to the Internet.
“To be an effeminate male, trans, queer in any way [at Sing Sing] […] those things other you really fast. No one wants anything to do with you.”
Back in the mid-‘90s, New York Governor George Pataki reinstated capital punishment. Charles J. Hynes — the Kings County District Attorney at the time — chose Shane as the first person slated for execution. In response, the city’s LGBT community rallied behind Shane. Articles about the case appeared in Out magazine, Lesbian Gay New York (LGNY, now Gay City News), and The Advocate. The New York City Gay and Lesbian Anti-Violence Project (AVP) organized a demonstration outside Hynes’s home.
In the end, the motion was successfully overturned. But while Shane was free from the death penalty, he was still facing a 50-year-to-life sentence.
Instead of despair and despondency, Shane has been a positive, active member of the incarcerated community. He’s earned two associate’s degrees, a bachelor’s in behavioral science, and a master’s in professional studies. He’s been a part of the Rehabilitation Through Arts program, has facilitated over a thousand hours of the Alternative to Violence program, written for The Marshall Project, and co-founded the Phoenix Players Theater Group.
“Those spaces are transformative,” he said. “They allow people to be okay with how people are different. We are always stepping over thresholds. You go into a space where there’s a community agreement, and you work hard to create a community. Doing that softens the edges [when] you step out of that and back into this other reality [of prison life].”
Shane is also highly involved in Sing Sing’s Buddhist group. Recently, he was struck by how his friend, a trans woman named Genesis, was treated by other members of the community.
“Some of the guys made an issue about her being there. As though just her existing in the world would bring them grief.”
It hardly needs stating that life as an LGBT person — especially a trans woman — inside a men’s maximum-security prison is a daily exercise in state violence.
“One of the first things you’re told in prison is ‘don’t hang around homos.’ It’s weird because you're automatically excluded. I often hear ‘you are so cool for a faggot.’”
Shane’s earlier threshold metaphor has its shadow side, too. For example, although he looks forward to weekend visitors, there’s also a part of him that doesn’t want to go: “After the visit, you get strip-searched.” Shane describes these strip searches as “so degrading. You’re stripping for someone and they're able to tell you to open your mouth, spread your ass cheeks, pull up your nuts.”
Strip searches also aren’t effective. A recent study showed that out of 23,000 prisoners in a California facility, strip searches found no weapons and only detected drug-related contraband a mere five times.
Even on Shane’s graduation day — a shining moment for any student — he felt the threshold.
"You're learning about yourself and about history. Then you graduate and feel you’re being witnessed in a new way. Then, of course, they strip-search it out of you. You cross a threshold where you are completely dehumanized.”
Michael Shane Hale (pictured left) meeting with composer Jake Heggie (center) and singer Joyce DiDonato (right) while working on the opera Dead Man Walking in 2023. Source: New York Times
Since Shane’s original sentencing, the New York State Legislature passed the Domestic Violence Survivors Justice Act (DVSJA), which requires a judge to consider the abuse a defendant has undergone and how it might relate to their crime. It took Shane years to realize that his relationship was, in fact, abusive. When abuse is all you’ve ever known, it becomes surprisingly difficult to recognize. Shane told me it happened at a domestic violence workshop at Sing Sing: “I was like, wait a minute, ‘did this happen to me?’ I asked, ‘Does this apply to same-sex couples?’”
Shane appealed for resentencing under the DVSJA. An official at the Brooklyn District Attorney General’s office asked him how they could know for certain he’d never commit such a heinous crime again.
“I was flabbergasted,” he told me, “because I thought, ‘damn you really don't know anything about me.’”
The Brooklyn DA's office signaled that it will oppose Shane’s motion for resentencing. None of his circumstances seemed to matter. Not the fact that he was a first-time violent offender, nor the crucial context of his background and intimate partner abuse, nor the 30 years he’s already served with exemplary behavior.
After that conversation with the Brooklyn DA’s office, all of Shane’s coping mechanisms broke down.
“Staying super busy, being involved in community projects […] all that stopped working. I was feeling very suicidal.”
Shane reached out to the Veterans’ Crisis Suicide Hotline (which he has access to from his time in the military) and they connected him with a therapist. He told me that getting more support for his mental health has been “life-changing.”
As Lennon’s book, The Tragedy of True Crime, hits shelves in September 2025, hopefully, people will gravitate toward Michael Shane Hale’s story and identify with the fraught complexities involved in his case. If LGBT people today can rally together like they did in the 1990s, perhaps the Brooklyn DA’s office will take notice and grant Shane’s resentencing request under the DVSJA.
After reading his story, researching his case, and talking to the man himself, it’s hard to imagine only seeing Shane for the worst thing he ever did. He’s so clearly an expansive, thoughtful, remorseful, multitalented person with one of the most preternaturally grounded and positive attitudes I’ve ever come across. He’s someone I’d love to hang out with.
More than anything, Shane has shown himself to be a person with so much more to contribute. Some may say he has not yet finished paying his debt to society, but every year Michael Shane Hale languishes behind bars is another year that the broader community is deprived of a person who has made it his life’s mission to grow and help others.
Published Sep 23, 2025
