Legal Weed, Unequal Justice: Mary Bailey’s Fight to Free Cannabis Prisoners

The Last Prisoner Project co-founder and 2025 DOPE Award winner’s fight for freedom

Mary Bailey stays in motion.

The event organizer, activist, and managing director of Last Prisoner Project runs a relentless schedule. From picking up newly released cannabis prisoners to producing the Hawaii Cannabis Conference in Honolulu, Bailey is constantly on the go—and that’s exactly where she wants to be.

Bailey has spent much of her life bringing people together around a greater purpose. A former concert promoter and community organizer, she’s always focused on creating spaces where people can gather and build something meaningful.

“I’m a humanitarian at heart. Kindness feels like the right thing to do, and helping others comes naturally to me. We all need support at different points in our lives.”

Mary Bailey, Managing Director and Co-Founder, Last Prisoner Project

A yoga and reggae fanatic, Bailey developed a deep connection to cannabis early on. Growing up in Florida during the height of prohibition, Bailey became “immediately fascinated” by the intersection of music and weed culture upon her first introduction.

In her twenties, that passion led Bailey to Hawaii and, eventually, inspired the launch of the Maui Cannabis Conference. By that point, she was already producing events through her company, Alpha Agency, including the Maui Yoga Festival and community block parties for the County of Maui Office of Economic Development.

“Stepping into the conference space felt like a natural next move. The goal was to create a space where local entrepreneurs could learn directly from leaders in the industry and build something meaningful of their own,” she explained.

That momentum put Bailey on a path that would ultimately change her life—and the lives of countless others.

The Birth of Last Prisoner Project

After hosting the second Maui Cannabis Conference, a social media video about a cannabis prisoner stopped Bailey in her tracks.

“It hit me like a ton of bricks. I realized it could have been me. I could have been the one locked up. I could have been separated from my daughter.”

Mary Bailey

Bailey’s friend, Maui-based activist Jeremy Jarvis, encouraged her to take action. Searching for a way in, she reached out to Andrew DeAngelo—who was already thinking along the same lines. He told Bailey he had been discussing the launch of a nonprofit dedicated to helping cannabis prisoners.

Bailey traveled to SXSW in 2019 to meet with DeAngelo, his brother Steve, and Dean Raise, manager of the reggae band Rebelution. That meeting became the spark for the Last Prisoner Project (LPP).

The group later sought guidance from Norm Reimer of the National Association of Criminal Defense Lawyers, with Harvard law graduate Sarah Gersten stepping in as executive director.

The newly minted team had a clear mission: support people serving time for non-violent cannabis offenses, help secure their release, and ensure a smooth return to society. The nonprofit began by building legal and reentry programs that connect prisoners with the resources they need to win their freedom and thrive once they’re home.

LPP quickly gained traction, earning support from industry leaders and cannabis-friendly celebrities.

The Greatest Reward of All

Asked about defining moments in her advocacy work, Bailey points to the people whose lives LPP has helped change. One that still stands out is the phone call with Michael Thompson, when he learned he had been granted an executive commutation from Michigan Governor Gretchen Whitmer.

“He had spent 25 years in prison serving a 40–60-year sentence and had nearly lost hope of ever being reunited with his family,” Bailey said.

Bailey also points to her connection with Stephanie Shepard, who served 10 years for cannabis-related charges. Shepard was eventually hired by LPP and worked her way up to acting executive director, a role she currently holds.

Yet one of the biggest moments was seeing Richard DeLisi walk out of a Florida prison. Once the longest serving nonviolent cannabis prisoner, DeLisi was eventually released thanks in part to the pro bono legal services he received through LPP.

“I will never forget standing alongside the DeLisi family and Richard’s legal team—Mariah Daly, Elizabeth Buchanan, and Chiara Juster—watching Richard walk out of the prison gates after serving 32 years of a 98-year sentence from one of the earliest RICO cases. One of my favorite moments that day was when Richard looked at us and said, ‘I’ve got the most lit legal team ever!’”

Mary Bailey

It’s these moments, and countless others, that led to Bailey being named the first recipient of the 2025 DOPE Award.

The announcement, part of High Times’ relaunch of DOPE Magazine, caught Bailey off guard. She said she was deeply honored by the recognition, but was quick to downplay it. Awards are nice, she insisted, but freeing someone who has spent years locked in a cell, separated from their family, is the only reward that really matters.

“Seeing a former cannabis prisoner truly thrive in their freedom is, without question, the greatest reward of all.”

Mary Bailey

The War on Drugs Isn’t Over

While Bailey and LPP have achieved many wins over the years, the work is far from over. She urged everyone in the cannabis space to take action, arguing that anyone benefiting from legalization has a responsibility to help those left behind.

“I feel strongly that anybody who has been in prison for cannabis or is currently incarcerated for cannabis is a true pioneer of the industry,” Bailey expressed. “It means that all of us in the legal industry should feel a moral obligation to join the mission to fight for their freedom.”

Bailey is clear that anyone can be an advocate, whether that means signing petitions or writing letters to people still behind bars. She urges readers to visit LPP’s Take Action page to find ways to get involved. The work won’t be finished until families torn apart by the war on drugs are brought back together.

Bailey leaves no room for complacency: “It will take all of us working together to achieve our mission of freeing every last cannabis prisoner.”