Stephanie Shepard: From Courtroom Shock to Advocacy for Justice

When I talked with Stephanie Shepard, she told me something that stopped me cold. “It took me about five years into my sentence to realize that this actually happened,” she said. “This is no big mistake. I’m really in prison and no one was coming out to save me.”

Five years. Half a decade to accept that a 10-year federal sentence for cannabis conspiracy was real. That her life as a real estate agent in Brooklyn was over. That the suburban kid who never touched weed until she was 28 was now federal prisoner 12345-whatever, teaching ESL classes in a federal prison.

The Courtroom That Changed Everything

Stephanie’s nightmare started with what seemed like simple kindness. Her ex-boyfriend had been arrested for cannabis, was sick in county jail with heart problems. His lawyer called her. Could she give him a place to stay if they got him out on medical bond?

She said yes.

Six months later, she answered one question from a judge in that courtroom. “I find this young lady responsible,” the judge said. “I’m gonna recommend he be released into her custody.”

An hour later, the lawyer texted. They were going to fight it. They said she was involved.

The day she was supposed to pick him up, her buzzer rang in Williamsburg. DEA and ICE agents. Warrant for her arrest.

“Still not believing that it’s going to happen,” Stephanie told me. “I think I’m going to have some issues. I’m gonna have to answer some questions. I never really believed that me would be getting into any serious trouble.”

120 Months

When the judge said “120 months,” Stephanie didn’t even know what that meant. No kids, so she didn’t think in months. Her attorney had to translate: 10 years.

Her sister, who’d flown from California to be there, screamed. Just screamed.

“I just turned to her and I wanted her to feel better,” Stephanie said. “So I smiled. It’s okay. It’s gonna be okay. We’ll work it out. It’s fine, calm down. And I’m smiling. And they take me back behind the doors and that’s when I scream.”

She was 41. A decade meant she’d be 51 when she got out. If she got out.

Learning the World Inside

Prison stripped away everything Stephanie thought she knew about herself. That first night at Danbury, exhausted from processing, she was led to a room with 12 bunk beds around 11 PM. Everyone woke up to see the new arrival.

The first two people who started asking her questions looked like men to her inexperienced eyes. She started crying. “I thought this was a women’s prison,” she said. “I was so green in what I was about to experience.”

But she learned. She found work teaching ESL, refusing the higher-paying factory jobs at Unicor. “I took a job that I felt good about, that filled my soul, which was teaching people English,” she told me. It paid maybe $80 a month, but it came with something more valuable: an office where she could be alone.

“Everywhere else on the compound you’re surrounded by people,” she explained. “There’s very few places that you have access to where you can be alone. But working in a classroom, that was my classroom. So I could go in there anytime I wanted to prepare lessons or just sit at my desk or read. That being alone at that time, having that time and that place to go to be alone, that was the most important thing about the job.”

She bounced between five different prisons. Flew commercially while in custody, alone, with just her prison ID and a note from the warden. When her father was dying, they took a week to approve her hospital visit. He died that morning. She flew to the funeral and back the same day, had to be back by 11 PM.

The Industry Bloomed While She Sat Inside

The cruelest part? While Stephanie served nine years of her sentence, cannabis became a billion-dollar legal industry. State after state legalized it. People on TV talked about the booming business.

“Once I started to see what the industry was turning into outside while I sat inside with other people doing the same thing,” she said, “there’s people on TV talking about how the industry’s booming and it’s legalizing state after state. But I didn’t know of anything like the Last Prisoner Project because they were just getting started. So I didn’t think there was going to be help for me.”

She got out in February 2020, right into the pandemic. The lockdowns didn’t bother her much. “I was used to being locked in a small space,” she said. “This was me locked up in my bedroom with a TV and comfortable bed and a kitchen steps away if I want to make whatever I want to eat. So it felt like the best version of the life I had already been living.”

Fighting for Those Still Inside

Now Stephanie works full-time for the Last Prisoner Project, the organization fighting to free people still serving cannabis sentences. They work for releases, policy change, reentry services, expungements. They give grants to people recently released on cannabis charges, connect them with pro bono attorneys for clemency filings.

“The great thing about what we do now at Last Prisoner Project is letting people know they don’t have to feel like that,” she said. “There are people outside here working for their freedom. And that’s got to feel better than what I experienced.”

She knows the Kevin Allens doing life sentences, the Parker Coldens doing 60 years for the same thing she can now buy legally within two miles of her house.

“After everything that I’ve been through, the biggest takeaway would have to be that it’s not over,” Stephanie told me. “It’s not over until these people who are sitting where I was sitting just three short years ago are home and moving on with their life the way I’m trying to do today. So it’s not over. We’ll win.”

She’s using her nightmare to end others’. That’s what real advocacy looks like.