From Teacher to Prisoner to Advocate: The Redemption of Michael Masecchia
Michael Masecchia spent decades shaping young lives as a beloved teacher and coach in Buffalo. Baseball, football, softball, and more, he dedicated himself to mentorship and community. But in 2019, his life was upended in an instant. A federal raid for cannabis, a swarm of law enforcement, and a harsh sentence threatened not just his freedom, but the very identity he had built. This is the story of how Michael survived the injustice, found purpose behind bars, and ultimately returned home, a story of resilience, redemption, and the transformative power of advocacy.
Before 2019, Michael Masecchia was known in his Buffalo community as “Coach.” For decades, he was a teacher, mentor, and youth sports coach, someone who poured his energy into helping kids build confidence and discipline both on and off the field.
But behind that life of service was also a lifelong relationship with a plant. Cannabis had always been part of Michael’s world, a connection that went from youthful curiosity to a quiet summer passion. “One of the reasons I became a teacher,” he shared, “was because I had summers off, and our growing season here is limited to the summer. So that’s what I did in addition to coaching.”
In 2019, that quiet connection would become the basis for the most devastating chapter of his life.
On the morning of the raid, Michael woke up to what felt like a scene out of a movie. Eight different agencies swarmed his home: Homeland Security, DEA, Border Patrol, State Troopers, all for what amounted to a half-ounce of marijuana, a few hunting rifles, and some edibles belonging to his teenage son.
“They had red dots, lasers, on my forehead and my chest,” Michael recalled. “They handcuffed my wife and my kids, dragged my son out of bed. We were treated like terrorists.”
The media headlines didn’t help. Overnight, Michael went from beloved educator to “teacher living a double life.” He described the feeling as “the worst thing you could ever experience.” His 30-year career, his reputation, his legacy, all gone in an instant.
And just when it seemed things couldn’t get worse, he was diagnosed with lymphoma.
Even behind bars, Michael found a way to teach again. At FCI Butner in North Carolina, he began by cutting grass and pushing lawnmowers, until word spread that a former educator was inside. Soon, he was teaching GED courses, helping other incarcerated men earn their high school diplomas.
But Michael, being Michael, he didn’t stop there.
Within months, he became the prison’s events and activities coordinator, organizing sports leagues and recreation for more than 1,200 inmates. “I developed my own leagues, flag football, bocce, darts, billiards,” he said. “I had my own office, three assistants, and I could come and go as I pleased. No one else had that luxury.”
Even in confinement, he found purpose.
Michael’s path to freedom began not in a courtroom, but in an act of kindness.
He stepped in to defend an 80-year-old fellow prisoner named Ralph, who’d been assaulted by another inmate. In gratitude, Ralph, a jailhouse lawyer, promised to “find something” to help Michael get home sooner.
Three months later, Ralph handed him a contraband newsletter from Last Prisoner Project. It included an application for legal assistance. Michael filled it out, skeptical but hopeful. Months passed before a letter arrived confirming his acceptance into LPP’s program.
That single act, standing up for someone else, set off a chain of events that led to his release.
With the help of LPP’s lead counsel, Elizabeth Budnitz, Michael’s team filed a compassionate release petition that, against all odds, was granted in 2025. “When they told me I was going home, I almost had a stroke,” he said. “Fifty guys were in my cell, hugging me, crying. It was unbelievable.”
After nearly three years behind bars, Michael walked out of prison and into the world a free man. His first stop? The airport restaurant. “I told the lady, ‘I was just released from prison today, and this is my lucky day. Can you help me activate this card so I can buy a burger and a beer?’ She said, ‘You know what? My cousin went through the same thing. I can help you out.”
That small moment of kindness meant everything. “I was floating,” he said. “Just seeing people, smiling, blending in, it was unbelievable.” When he finally reunited with his family, the moment was pure chaos and joy. “They were all jumping, screaming, crying. It was unbelievable.”
Now home and in remission from cancer, Michael finds peace in life’s simplest freedoms, driving his Jeep, walking his dogs, cooking with his wife, and tending to his garden. “Being able to call my kids anytime I want, sit on my porch in the sunshine, it’s unbelievable,” he said. “Those are the things that matter.”
But even in peace, there’s a lingering sense of injustice. “I was 41 days short of a full pension,” he shared. “I can’t get my Social Security for another three years. I’ve worked my whole life, but I’m still starting over.”
As cannabis legalization continues to sweep the nation, Michael still struggles to make sense of the contradiction. “What doesn’t our government get?” he asked. “Cannabis is everywhere. I walk my dog and smell it on every corner. People shouldn’t be in prison for this.”
He’s right. Yet thousands still are.
Michael’s story is a reminder that justice delayed is justice denied, and that every name behind bars represents a family, a legacy, a life interrupted.
When asked what he’d say to others still incarcerated for cannabis, Michael didn’t hesitate. “Be good to people. Show humility and grace. That good karma comes back to you. And reach out to Last Prisoner Project. If it wasn’t for Ralph finding them, I’d still be there.” At the end of our conversation, he paused and smiled. “It’s like a miracle that they even exist. Who else fights for people like that?”
Michael’s journey isn’t just about freedom; it’s about faith, humanity, and the power of connection.
His story reminds us that compassion can change lives, that justice requires action, and that even in the darkest places, light finds its way through. Because when one person goes home, we all move one step closer to freedom.
--
Michael’s journey reminds us that justice is not just about laws on paper, it’s about the lives they touch. From the small joys of gardening and walking his dogs to the profound relief of being reunited with his family, Michael has reclaimed his life. But thousands remain behind bars for the very same “crime” that turned his world upside down.
His story is a testament to hope, compassion, and the tireless work of organizations like Last Prisoner Project. It is a call to action: to fight for fairness, to advocate for those still incarcerated, and to never underestimate the human spirit’s ability to endure, to mentor, and to heal, even in the face of profound injustice.
