Stephanie Gregg Shares the Hardships of Being a Single Parent of Two While Their Father Serves 15-years for Cannabis

Stephanie Shepard • September 6, 2023

Last Prisoner Project's Stephanie Shepard and Stephanie Gregg discuss her experiences as a single co-parent of two children, Presley, 11, and Patron, 14, whose father, Jason, has been in prison for cannabis for nine years. Jason was indicted by the federal government and sentenced to a 15-year sentence for cannabis distribution. Stephanie shares her experience of trying to live a normal life while her husband serves his sentence. Stephanie discusses her children, community involvement, and the challenges she and Jason have faced during his time in prison. Last Prisoner Project emphasizes the need for reform of the prison system for drug offenders.


LPP: 

Tell me a little bit about yourself, Stephanie. How did you come to be speaking with me today?


SG: 

Jason was my childhood crush. I moved back to Mendocino County from Southern California to be with him. We had our 2 sons, Patron and Presley, within the next four years. Patron is going to high school, and Presley to middle school.


LPP:
 

How old was Presley when the feds indicted Jason for cannabis charges?


SG:

Presley was three weeks old.


LPP:
 

You live in the Emerald Triangle, the heart of California cannabis. Did you think, nine years later, you would still be experiencing the collateral consequences of a cannabis charge? 


SG:

It's what I've grown up seeing here. It's what I know. It's normal here. Different from the rest of the world. I had never seen anyone get more than like five years. Very few people got long sentences. I really thought he would get out. I didn't think he would do as much time as he has, but they did give him 15 years in federal prison.


LPP:

As a new wife and mother of two young boys, what did Jason's incarceration do to your relationship? As a couple and as a family?


SG:

Sadly, the system is not set up to keep families together. Jason is still one of my best friends, but after the first couple of years, we had our ups and downs and eventually ended up separating. It's already such a lonely road, that when you put that pressure on someone else, and you're trying to make a relationship work, we realized that we got along so much better as friends. Even if Jason didn't understand what it was like for me out here, I understood what it was like for him in there, so when we come together as friends and support each other, it’s healthy for the kids because they feel when we’re strong, and friends and he's involved. They're solid. We still talk every day, and he's a really good co-parent. He still helps with the boys. Last night, I had to take the kids back-to-school shopping, and teenagers can be tough sometimes. And so I had to get Jason on the phone with his son, and he just gave them the “respect mom” talk, and “she does a lot for you” talk, so he's still very much a part of their lives, as much as he can under the circumstances.


LPP:

How important is that continued connection for both Jason and your sons?


SG:

It’s very important! It keeps Jason grounded. There is not a lot in the way of mental health services available in prison. There were times when he would have benefited from some assistance, but he had to get through it on his own. He’s great today, but the kids have surely been his anchor. The boys have a lightness about them that neither Jason nor I had as a kid. I've done a lot of work to make sure that they don't carry this trauma.


LPP:
 

What kind of father was Jason before being taken away?


SG: 

Jason was a super hands-on dad. Jason was that guy that changed diapers and did the grocery shopping, and he loved it. We contributed a lot to our community. We were super involved. He was at every school function. We weren't just out living some crazy life. That's one thing we had in common. Neither of us had the easiest childhood, and that's what we both really wanted was a family of our own. He was a really good dad, and he is today as well, the best that he can be.


LPP:
When you found yourself a single mother, having to take care of your children, did you have a lot of support?


SG:

I don't. This isn't anything negative to the community or to family, I just don't think people know what to do. There's actually a lot of judgment. I did have love and support, but not where I needed it. People don't know what to do. But I'm also a very prideful person that made it always look like I was good, so I think that probably put a wall up from anyone who may have tried to support me differently.  Some people will say straight to your face, “Well, there are consequences.” When people can be so harsh, you put up those walls. So to answer your question, yes and no. Some wonderful people reached out at first, but the years continue to go by and they disappear. I suffered silently. I would not know what I was made of today if I hadn’t gone through that. And my relationship with God is everything.


LPP:

Becoming a single mother almost instantly, you not only suffered emotionally but also financially. What were the hardest of times that you experienced?


SG:

There were times I could barely afford really important things that were necessary. We were just in survival mode. It just felt like it was us against the world. I saw what government assistance did to my mom, so I didn't want to utilize the government. I didn't get on any kind of welfare, or any of the things that I probably should have put my pride down at times and accepted it.

But I made it. It forced me to figure it out. It’s very difficult for families who lose their provider.

Strangely enough, It's not the people that you're closest with that try to help you. It's not the people you’ve helped make money. It's not the people that you helped with their bills. Jason was very generous. He really believed that when you let money go, it comes back to you. So it's funny. It's not the people you think that will be there, but some wonderful people do come out of the woodwork. LPP gifted me a Family Support Grant, which paid for half of the kids' school tuition for that year because I've put them in private school. I want them to have every opportunity that Jason and I didn't. We were really grateful for that. People think prison is free, and it's not free. That's why I put money on his books every single month, no matter what, no matter what my month looks like. I was lucky to have some childhood friends that just loved me through all the stages. But for Jason, he didn’t have that support. I feel like he got treated like he’d died. This is one of the reasons I'm so protective when it comes to him, he deserves better.

LPP:

How have you cared for yourself during such a trying time? Has Jason shared with you how he gets through his days?


SG:

I had an amazing priest, Father Damien, up at the monastery. I would go up there and just cry, and I would go talk to him about everything that I was going through. He was like a dad to me. Jason works out, and he loves the Constituent Newsletters that he gets. All of that means a lot.



LPP:
 

If you could send President Biden a message, what would you tell him? What change would you like to see?


SG:

First, free Jason Gregg! He has served his time. Let him out so he can experience what's left of his sons' childhoods, they need him. His son's going into high school, his youngest is going into middle school. He's missed all of it. It's time.


As for change, starting with the freeing of every person incarcerated for cannabis. There are also not many educational opportunities or adequate mental health support systems available. Things that can assist in rehabilitating someone are not a priority. Jason will have a lot of work to do when he gets out just to try to get re-established. He has taken every program that he has been offered, and I’m proud of him for that. He's such an amazing human that he doesn't put any negativity on us. He's always positive in the way he talks to the kids, and he asks about them, their day, their sports, it's never about himself. Jason's the strongest person I've ever met. I just have so much respect for him.


LPP:

If you can give our readers one final glimpse into who Jason is, how would you describe him?


SG:

Jason is just a good-hearted country boy from Willits who loves his sons, his community, and his family.


Take Action
By Stephen Post June 13, 2025
As families across the country come together this Father’s Day, thousands of children are spending the day without their dads—not because of violence or harm, but because their fathers remain locked away for cannabis-related convictions. In many cases, these men are serving long sentences for conduct that is now legal in much of the United States. Despite cannabis being decriminalized or fully legalized in the majority of states, the human cost of prohibition continues to devastate families—especially those in historically marginalized communities. These are fathers raising their children through prison phone calls and video visits, relying on letters and photographs to stay connected while missing birthdays, report cards, and everyday moments. Behind every sentence is a story. And behind every prison wall is a child wondering why their dad can’t come home. Daniel Longoria is one of those fathers. A U.S.-born, Hispanic man serving a 30-year sentence for a nonviolent cannabis offense, Daniel has not seen or held his children in years. The pain of distance, separation, and injustice weighs heavily on him. He shared the following: “When a Dad has not seen his kids, held his kids and who's son no longer speaks to him because I am over 1,000 miles away from home without a good cause puts such a heaviness in my heart that if I did not have God to turn to, I might have probably already ended my life. My son has now been diagnosed with Mental Behavior Disorder and has attempted suicide three different times. These things as a Father kill me inside because I was a great Dad and my kids loved me, and so Father’s Day is really hard to celebrate anymore. How can I celebrate this day, when I know my kids are struggling out there because of a plant that many states are now making millions, if not billions, of dollars off of it? I have also become a grandfather of two and have yet to meet them. I keep the faith and remain strong in the Lord. One day, I pray to be home and this nightmare be over.” Daniel’s experience is not an isolated one. At Last Prisoner Project, we work with dozens of fathers currently incarcerated for cannabis convictions—men who are missing milestones, parenting through prison walls, and holding on to hope for freedom. These dads include: Terrence Pittman – Father of five, serving a 30-year sentence Rollie Lamar – Father of six, serving an 18-year sentence Antoine Turner – Father of three, serving a 13-year sentence Malik Martin – Father of six, serving a 10-year sentence J’lyne Caldwell – Father of four, serving a 5-year sentence Vinh Nguyen – Father of two, serving a 6-year sentence Rendy Le – Father of two, serving a 5.5-year sentence Sean Scott – Father of one, serving a 5-year sentence Sean Scott’s story is particularly heartbreaking. A former Division I football player and successful real estate entrepreneur, Sean is serving over half a decade for a nonviolent marijuana offense involving nine kilograms and a legally owned firearm. While he remains proud of his past and hopeful for the future, he’s devastated to be missing out on his two-year-old son’s life. “This is my third time away,” Sean said. “And it’s extremely difficult to just watch my son grow and miss another holiday with him.” His fiancée is raising their son alone while also caring for Sean’s elderly mother. Sean is one of many fathers who should be home—not behind bars for something legal in so many parts of the country. Then there’s Rendy Le, a father of two, who reminds us what’s at stake. “You can always make money—but you can’t always make memories,” he said. “Cherish the good times.” It’s a sentiment echoed by every man we work with: time is the most precious thing they’re losing. Despite all this injustice, we also see the other side—stories of reunion, resilience, and redemption. Bryan Reid is one such example. After serving six years of a 12-year cannabis sentence, Bryan is now home and rebuilding his life with his children. “When I went in, my son was just one and my daughter was three,” Bryan told us. “I missed every first and last day of school. But now? Now I’m their sports dad, Santa, and biggest fan.” In the 15 months since his release, Bryan has made new memories—picking his kids up from school for the first time, visiting trampoline parks, and watching his oldest daughters graduate college. “Watching them grow into strong, independent women and seeing how hard they’ve worked for everything they have is nothing short of incredible,” he said. “It was an honor to stand beside them.” Bryan’s return to fatherhood, though hard-earned, is a reminder of why we fight. No one should be separated from their children over cannabis. No child should grow up wondering why their father is in prison for something now sold legally in dispensaries across the country. This Father’s Day, let’s do more than celebrate. Let’s commit to changing the laws, freeing the fathers, and reuniting families. Join us in advocating for clemency, resentencing, and restorative justice—for Daniel, Sean, Rendy, and the thousands of others still waiting to come home. Want to help this Father’s Day? Share their stories and donate to support our work! Bryan Reid Enjoying Freedom
June 12, 2025
Wednesday, October 15 at Sony Hall in New York City Notable Guests Include Carmelo Anthony, Calvin “Megatron” Johnson, Dr. Wendy & Eddie Osefo, Fab 5 Freddy, Keith Shocklee and Studdah Man of Public Enemy, and Guy Torry with a Performance by Joy Oladokun PURCHASE TICKETS & MORE INFORMATION
By Stephanie Shepard May 14, 2025
When Alexander Kirk walked out of prison on December 10th, he stepped into a world that had shifted beneath his feet. But the shift wasn’t universal. In Iowa, where he lives, cannabis is still fully illegal. Drive two minutes across the bridge into Illinois, and that same plant, once the root of his decade-long incarceration, is not only legal but a booming, billion-dollar industry. That contradiction sits at the center of Alex’s story. He’s a father, a mechanic, a reader, and a deep thinker. He’s also someone who spent more than ten years of his life behind bars for the same substance that dispensaries now sell with flashy packaging and tax revenue incentives. “It’s crazy,” he says. “One side of the bridge is legal, the other side isn’t. It’s hard to believe.” A Life Interrupted Alex’s most recent sentence—ten years in federal prison—started with a bust that was as much about timing and proximity as anything else. He was on federal probation for a previous cannabis offense. A raid at a residence he didn’t live in, but where his truck was parked, ended with a federal indictment. A tip from his child’s mother, who was angry about a disagreement over vacation plans, helped open the door for the investigation. “She made a call, gave them a tip,” Alex recalls, without bitterness, just clarity. “And that’s all it took.” The charges? Conspiracy to distribute less than 50 kilograms of marijuana—a charge that, while less than the quantities tied to large-scale trafficking operations, still carried weight under federal law. He received 80 months for the new charge and another 40 months for violating parole. The math added up to a lost decade. “I had already done ten and a half years the first time,” Alex says. “I was institutionalized. Prison became familiar. It’s where I knew how to move.” But even when you know the rules, prison isn’t easy. The hardest part for Alex wasn’t the food, the routines, or the guards—it was missing his children growing up. “I got five kids. Three of the older ones talked to me after and explained how I chose the streets over them. That was hard. But it was true.” He reflects on it now with a kind of painful honesty: “I didn’t want to pay for weed, so I started selling it. I smoked, and I hustled. Eventually, it got out of hand.” Knowledge Behind Bars Alex didn’t spend his time in prison passively. He worked in the prison garage, learning to fix cars—something he’d loved as a kid. He dove into books and self-help titles. One that stuck with him was The Voice of Knowledge by Don Miguel Ruiz. “That one changed things,” he says. “It helped me realize everyone’s got their own story they’re telling themselves. That helped me stop taking things so personally.” He also began thinking about the world beyond prison. He drafted a business plan for a youth program designed to keep teens from ending up like him. “I wanted to show them they had options,” he says. “You don’t always get that when you grow up in survival mode.” The Politics of Legalization What’s jarring about Alex’s story is not just the sentence—it’s the fact that it happened while the national conversation around cannabis was changing rapidly. By the time Alex was halfway through his sentence, multiple states had legalized recreational marijuana. Billion-dollar brands were being built. Politicians were posing for ribbon-cuttings at dispensaries. Celebrities were launching product lines. And people like Alex were still behind bars. “It’s unjust,” he says bluntly. “There’s no reason someone should be locked up for weed while companies are out here getting rich off it. The little guy got crushed. They legalized it after locking us up, but didn’t let us out.” The irony was never lost on him: that he was doing hard time for something that was now a tax revenue stream in neighboring Illinois. A Second Chance and Real Support Alex’s sentence was reduced under the First Step Act—a federal law aimed at correcting some of the harshest penalties in the justice system. Thanks to that and a longer placement in a halfway house, he was released earlier than expected. Through a friend, he reconnected with a woman from his past who introduced him to the Last Prisoner Project (LPP) . At first, he was skeptical. “We never heard about people helping folks like us. I didn’t think it was real.” But he gave it a chance—and found not just advocacy, but consistency. “Even getting emails, updates, hearing from people… that helped. It made me feel like someone gave a damn.” Through LPP, he learned that he qualifies as a social equity candidate in states with legalization programs. That means access to business licenses and support that could help him transition into the legal cannabis industry. He also learned he might qualify for early termination of his probation—a process he’s now pursuing. “I want to get into the legal side,” he says. “I know the game. I lived it. Now I want to do it right.” Life After Prison Alex is currently working in the halfway house kitchen. He’s trying to stay grounded, focused, and patient. Reentry is never easy. “You come out and everything is fast. You feel like you’re behind. But I remind myself: it’s not a race.” He’s rebuilding relationships with his kids. He’s focused on starting a business—maybe something in cannabis or something with cars. He hasn’t fully decided, but he knows he wants to help others, too.  “There’s still a lot of people inside,” he says. “And they shouldn’t be. Not for weed. If we’re really gonna legalize it, let’s legalize it for everybody. That means letting people go.” “Get to Know Their Story” Alex doesn’t want pity. He’s not asking for a handout. What he wants is what most people want: a chance to live free, to work, to be with his family. To matter. “Just because someone’s been to prison doesn’t make them violent. Doesn’t make them a bad person. Get to know their story.” Alex’s story is one of transformation, not because the system rehabilitated him, but because he did the work on his own. Now he wants to use his experience to change the system itself. He’s already started.