Sanctuary Spotlight: Stephanie Shepard, Last Prisoner Project

  • By Jake May
  • Feb 25, 2022

Stephanie Shepard: Development Associate & Advisor, Last Prisoner Project

For more information on Stephanie Shepard, check out this insightful, detailed piece about her journey written by our friends at Dutchie, which served as the basis for many of these questions. All 10 Sanctuary locations in MA and FL are currently collecting donations to the Last Prisoner Project in support of the Roll It Up For Justice program referenced below. Be sure to follow their socials listed below and visit their website for more education, action items and opportunities to contribute. The following interview has been lightly edited for length and clarity.

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After being implicated without proof for intent to distribute cannabis in connection with your ex-boyfriend, you mention working and living as normally as one could on pretrial. What do you remember about the day your real estate license renewal was denied, and how did that impact your mindset?

That day, I had so much on my mind because I was on pretrial at the time. I’m still trying to work, abide by the rules and regulations, and I still hadn’t told my parents I was even in trouble. My brothers and sisters knew, but they were sworn to secrecy about it because I didn’t think it would end the way it did. I went into my office, sat down at the computer and began the application process. I had done that several times before, so I never noticed the questions about, “Are you a felon? Do you have a felony pending?” It’s automatic, no, no. This time, I looked at it, and the first question was, “Do you have a felony?” I clicked no. Then, that second question: “Do you have a felony pending?” When I clicked yes, that’s when my application was denied.

That worried me because, once I got out, I thought, “What am I going to do?” I’m starting a whole new life at this point because I can’t sell real estate anymore in New York. When I went on probation in California, it’s a case-by-case basis, so there was an opportunity to continue my real estate career here, but I wasn’t passionate about it anymore. I had a different path that I saw for myself, and that was working to free those incarcerated for cannabis, bring them home humanely and with the knowledge of self-worth that you are stripped of in prison.

How does the pretrial process negatively impact people’s lives even before a verdict is delivered?

It’s a lot to carry, and I was on pretrial for one year. I didn’t want to worry my elderly parents with it, and I thought there was no way that someone without a criminal history is going to go to prison for 10 years; I was just trying to go day-by-day. I also had to drug test during this time, so I would call a number, and if your color came up, that means you had to be down there first thing in the morning. That’s a lot on your head; you’re thinking about it at night and then they want you to come first thing in the morning. Now, you have to rearrange your schedule because it’s random and you don’t know. Now, you’re messing with my money again. 

If I hadn’t been found guilty and was sent back to my life, it would have still been ruined because the feds are coming to your job, going to your clients, going to your neighbors. They’re putting this narrative out that you’re a criminal already. Even if I had been able to go back to my job, you’ve already gone to my broker and told him that I’m a drug dealer. You’ve already gone to my coworkers. It’s a small community; New York’s full of people, but it’s a small real estate community. You’ve already put out to my clients that I’m a drug dealer, so the harm that’s done is done either way the day I was arrested. 

You mention meeting Evelyn La Chapelle (now LPP’s Community Engagement Manager) while in prison. What do you recall about those early interactions? Did you foresee your paths becoming so intertwined? 

No, actually. When I met Evelyn at Victorville, due to prison politics and who I was friends with and who she was friends with, we weren’t meant to be friends; I just saw her in passing. One night, we both stayed up late in the TV room and watched the news because we heard there was a story about the marijuana business; she was in for marijuana charges as well. She and I were sitting there in the dark, and we watched this newscaster ask a woman, “So, the cannabis business, how’s it going for you?” And the lady was like, “Oh, business is booming” and went into how well she was doing in the industry. Evelyn and I looked at each other, and we were just like, “Wow.” Evelyn’s away from her daughter doing a lengthy  sentence and I’m sitting in there away from my family. My father was very sick at the time, and this lady is on TV bragging about how business is booming. It was not lost on us that Evelyn is a Black woman, I’m a Black woman, and the woman on TV had blonde hair and blue eyes. After that, we felt a shared connection in how messed up this system is. 

How does long-term incarceration such as this impact the fabric of a family? How does one cope with the effects of that lost time upon returning home?  

The bad thing about time is it’s fleeting. I carry so much guilt from asking my sisters and brothers to hold this secret from my parents. I hold guilt that I didn’t give my parents the opportunity to support me. I took that away and, with my dad passing away while I was incarcerated, I wasn’t even able to tell him how sorry I was. I told him over the phone, but it’s not the same. When I came home, and because of the way the system is set up, I still needed help and my sister’s assistance. She was already supporting me for those 10 years while I was in prison and I didn’t want for anything–she supported me in that. Then, once I was released, she still supported me; I was living under her roof for the first year of my release. 

The grants we provide to people are so important because having that sense of self-reliance is so important. Starting your own bank account, being responsible for your own money, those things all really matter to your self-esteem. To come out of prison and be given a grant saying, “This is to help you get on your feet” is one of the main things. We give grants to be used for housing, first and last month’s rent, a used car–it can be life-changing for some people. I’m very, very proud of that because having to carry that weight of still being a burden is one of the things that’s hard to get past. 

You briefly mention the negative stigmas around how prisoners speak, look and behave. What are some common misconceptions that people hold in that sense?


First of all, people have an idea of what a felon looks like or a prisoner “looks like.” That’s not the case. The good thing about the normalization of cannabis use with cannabis moms and things like that is you don’t know who it can happen to. I felt like if this could happen to me, it can happen to anyone. I just have a four-to-five percent greater chance of it happening to me because I’m Black.

Even while I was in prison, I flew alone while in custody, going from one prison to another several times. I remember leaving Minnesota and going to Victorville; I was given $14, a prison ID and a letter from the warden. It had my mugshot on it and explained that I was a prisoner, but there’s no system set up for this. I step up to the [TSA] counter. “Can I see your ID?” I hand them my prison ID while everyone else is handing their drivers’ license. The lady looks at it, then looks back at me; I’m in gray sweats, a mesh bag. She says, “Oh, just one moment,” gets on the walkie-talkie, calls for a supervisor and I have to go through extra pat downs. This whole time, I’m feeling like I want to get back to prison and like it’s too uncomfortable for me to be out in the world with this stigma.

To want to get back to prison, to want to get back to your captors, it made me so afraid of how I would feel when I’m out permanently; I’d never had those feelings before. Being a felon and having to fill out a lease application for an apartment, marking down Yes to, ”Have you ever been convicted of distributing a controlled substance?” right beneath, “Are you a sex offender?” Obviously, it’s there as a roadblock between you and getting an apartment. The reason I share my story is because I don’t typically look like someone who would go to prison, but there is no typical “look.”

What do you remember about your first Last Prisoner Project fundraiser in San Francisco? What were some of the first steps toward your larger involvement with the organization? 

[Evelyn and I] went to Phoenix for the drug program, which was the only way I could get time off. We opted to go to a drug program because of our “marijuana addiction,” got through that program and got out with a year taken off our sentences. I was allowed to go to a fundraiser that the Last Prisoner Project was holding, and Evelyn was telling her story. I had gotten permission–I still had my ankle monitor on–to go down and listen to her tell her story. I saw the reaction of the people in the room, and that’s when I decided I wanted to tell my story, especially if my story can help anybody realize that people shouldn’t be doing 10 years as a first-time, non-violent cannabis offender when you can go to any corner in any city where it’s legal and purchase cannabis. I remember videotaping her telling her story and, in listening back, you can hear me crying. Her story, like so many others, is just so wrong. 

That’s when I met Steve DeAngelo, Mary Bailey and Sarah Gersten, and I began utilizing their platform to share my story. As time went on, I was ready to get a new job while moving away from the comfort of the Starbucks job I got two weeks out of prison. My confidence level had grown and I was ready to move on to something more worthy of my background. [Last Prisoner Project] said, “We would like you to work with us full-time.” I started working with them seven months ago and it just feels great to get up every day, be able to do something that I’m passionate about and still take care of myself. 

Is there a particular arm or activity of Last Prisoner Project for which you have a particular affinity? 

One is definitely being able to communicate with our constituents or their families. I speak to many family members of our constituents. I went to Atlanta recently and had dinner with one of our constituent’s daughters. He’s done 14 years in prison for cannabis. He and his daughter are best friends; she’s now 24 years old and in law school. To be able to meet her, sit down to a meal with her, talk to her and let her know that if she needs anything, we’re here, makes me satisfied. She’s received a grant that I’m sure can help out when you’re in law school–that is one of the big things.

Another is when the constituents get to come home. Being there for Corvain Cooper‘s homecoming, when he came home from doing what was supposed to be a life sentence for cannabis, seeing him with his family, seeing these things that I didn’t really have when I came home. When I came home, my father had passed away and a lot of things had happened. It wasn’t the same kind of celebration that a homecoming warranted. 

We have a program called Roll It Up For Justice, and the donations come from the consumers, from the patients, from those people who are coming in and exercising their privilege and right to purchase cannabis, take it home, consume it and not go to prison for it. We work with over 300 dispensaries and brands across the country, and when people go in, they can donate [at point-of-sale stations]. Through that, we were able to give over $600,000 last year in direct grants helping people have money on their accounts in prison, for their kids, caretakers for their children and more just through the grant. Knowing these things are helping with roadblocks I know and knowing how they feel is what drives me. It makes every day worth it. 

From where do you draw the strength to tell your story?


I draw strength from the people who were strong for me. When I was incarcerated, that was my sister. I have to do something great with this for my sister. I’m the youngest of seven, and my father was always supportive and super proud of everything I did. If I had had the opportunity to explain my position, my outlook on cannabis and talk to my dad about those things, I feel like, if he were here right now, he would be cheering me on. He would be so proud of the work that I’m doing. I have to get to that point where I know for a fact that what I’ve done has mattered, that he sees it and that he would be so happy that this is the path that I chose.

As someone with their fingers on the pulse of the cannabis industry, what indicators of meaningful change do you look for? Where are some of the major areas where work toward equity and justice remain incomplete or lacking attention/resources?

Obviously, second-chance hiring is a big thing that needs to be addressed. These are people who, although unlicensed, essentially did what you are now doing. They shouldn’t be shut out of an industry that, for some people, has been their life’s work; people who grew up in families who grew [cannabis]. For there to be no place in the industry for us–it’s a hard pill to swallow. It makes me say, “How much of the culture do you care about, and how much is it the money that you’re making?”

The good part is we work with a lot of great brands who understand, have been impacted in some areas of their life or simply realize how privileged they are to be able to do what they’re doing in this day and age and at the scale that they’re doing it. They could be behind bars for 50 or 60 years. Parker Coleman‘s doing 60 years–he’s a young man. When brands and dispensaries recognize that and want to be involved, that gives me a lot of hope for these people coming home, knowing that there’s a place for them out here and that there’s a community that welcomes them and isn’t going to shun them. I’m seeing that, and we have a lot of great partners. There may be some who don’t see it as their problem, but at the end of the day, it’s everyone’s problem.

For people and companies looking to help create positive change in the space, what are some immediate steps they can take?

On our website, we have a Take Action page. It can be something as simple as signing a petition. We have a petition right now called A Time to Heal that people can sign calling for President Biden to release these prisoners. It’s something as simple as signing that or sharing social media posts; our social media posts are primarily geared towards education, what’s going on, new bills that are being passed, new goals that are being presented. Go there, get educated and take those next steps. We have a newsletter where we do a lot of calls-to-action. People can read it, sign a petition that’s posted, share media posts and have these discussions in rooms where they wouldn’t normally be had. 

Even if someone isn’t into consuming cannabis or doesn’t care about cannabis, there’s another piece. Your tax dollars are at play; it’s upwards of $40,000 per prisoner. I don’t know a lot of people who find me so threatening that they would like to contribute to keeping me behind bars. If you can drive down the street and see someone walk into a dispensary and walk out with a bag, you can have a discussion about the people who are incarcerated for that reason.

What are you looking forward to the most within the cannabis industry? 

In an industry sense, more second-chance hiring. As these people have the chance–and I feel like we’re so close, this day is coming–there’s going to be a lot of people looking for work. For the people who have the opportunity to hire these people, I want to see them take it, and they’ll have one of the best employees ever. A lot of people don’t want to go back. If you’re looking for a good honest employee, hire a felon. 

Who are some of the role models, collaborators or change-makers you value in the space?

Coming out now and seeing how the industry has changed and grown, it’s really a good thing. Seeing so many women-owned brands out there is amazing to see; Miss Grass, for example. Her Highness is another one with two women who have made a brand geared toward women and are dedicated to giving back to women. Josephine & Billie’s is a new dispensary in Los Angeles opened by two really strong women who just made it happen. The fact that they’re women of color just makes it even more personal for me. There are so many women doing great things in this industry; Roz McCarthy, Nichole West, Maisha Behati, Marie Montmarquet come to mind. The women of Supernova are another; there are just a lot of women out there who are standing out to me.

Any final thoughts?

I just want everyone to exercise empathy because, like I said, if it happened to me, it can pretty much happen to anyone. You can’t really be a straighter arrow than me, except for the alleged cannabis dealing. If you are someone who’s going in and purchasing or consuming, it can happen to you as well. Just keep that in mind and give people a chance to come home and continue their life without the stigma.

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