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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 April 1, 2025
In recognition of Second Chance Month, The Last Prisoner Project (LPP) reaffirms our commitment to ensuring that individuals impacted by the criminal legal system receive the support they need to successfully reenter society. At LPP, reentry is at the core of our mission—providing resources, advocacy, and direct financial assistance to those returning home after incarceration for cannabis-related offenses. We would like to honor the amazing advocates and lawmakers who tirelessly working to offer second chances to our constituents who have been experienced injustice due to the war on drugs. Through strategic policy efforts, LPP has contributed to the clearing or pardoning of over 200,000 cannabis-related records, including Governor Wes Moore’s historic clemency action in Maryland, which impacted more than 150,000 people. LPP is proud to support key pieces of upcoming legislation that could propel this movement forward like the Reentry Act of 2025, which would allow states to provide Medicaid coverage to incarcerated individuals 30 days before their release, ensuring they have access to critical healthcare services. Additionally, we endorse the reauthorization of the Second Chance Act, which has provided essential funding for reentry services nationwide since 2008. We are grateful for the efforts of groups like Just Leadership USA and the Council for State Governments for leading advocacy on these bills. LPP's Executive Director, Sarah Gersten said, “At Last Prisoner Project, we believe that no one should be denied a second chance—especially those who were unjustly criminalized for cannabis. True justice means not just release, but real opportunities to rebuild. We call on lawmakers, businesses, and communities to join us in ensuring that every person impacted by cannabis prohibition has the resources and support they need to thrive.” In 2024 alone, LPP provided over $340,000 in reentry grants, contributing to over $3.5 million in direct financial assistance distributed since 2019. These funds play a critical role in easing the transition for those leaving incarceration, helping them cover essential expenses as they rebuild their lives. LPP has also assisted over 400 constituents directly through legal and constituent service programs, helping to eliminate more than 300 years of excessive sentences. Behind these numbers are real people—like Richard Delisi, Michael Thompson, and Kyle Page—who have turned their experiences into platforms for advocacy and entrepreneurship. The Michael Thompson Clemency Project continues to push for justice for those still incarcerated. Entrepreneurs like Kyle Page, Mario Ramos, Donte West, and Alicia Deals are building businesses that create opportunities for others affected by cannabis criminalization. Leaders like Stephanie Shepard, LPP’s Director of Advocacy, use their platforms to fight for lasting policy change. This Second Chance Month, we celebrate the resilience of our constituents and reaffirm our commitment to ensuring that every person impacted by cannabis prohibition has the opportunity to rebuild and thrive. Join us in advocating for policies like the Reentry Act of 2025 and the Second Chance Act reauthorization to create real pathways to justice and opportunity. By joining forces and advocating for meaningful change, we can pave the way for a society where everyone benefits from the opportunities and benefits of legal cannabis without fear of discrimination or injustice. Together, we can create a brighter future for all. Donate here to help support second chances for our constituents.
By Adrian Rocha March 31, 2025
At the Last Prisoner Project (LPP), we believe that no one should remain behind bars or face the lifelong burden of a criminal record for cannabis-related offenses. That is why we have been working since 2021 to ensure that retroactive relief is provided for individuals in Hawai’i who have been criminalized by outdated cannabis prohibition laws. And this week, we got one step closer to justice. Last year, we helped write HB 1595 (now Act 62), which created a pilot project for state-initiated expungement of non-conviction marijuana possession records on Hawai‘i Island and identified over 2,200 records for relief in Hawai’i. Now, HB 132—which just passed the legislature last week—would help speed up their expungement if signed by the Governor. Unlike traditional expungement processes, which require individuals to apply and pay fees, this project shifts the burden to the state, ensuring that those eligible for relief receive it without unnecessary barriers. After just one month of implementation, the pilot project identified 2,268 records potentially eligible for expungement. As of December 13, 2024, the Hawai‘i Criminal Justice Data Center (HCJDC) had reviewed 640 of those cases, leading to 81 expungements, 112 cases pending expungement, and 33 denials, with 414 cases still under review. These numbers demonstrate both the necessity and the challenges of state-initiated expungement, particularly in cases where arrest records lack clear substance classification. While Act 62 was a major step forward, a technical issue in the Hawai‘i Criminal Justice Information System (CJIS) has made implementation far more burdensome than anticipated. Currently, the system does not consistently specify whether a charge under section 712-1249, Hawai‘i Revised Statutes (HRS), was for marijuana or another Schedule V substance. This lack of detail forces HCJDC staff to manually search through arrest and court records, significantly slowing the process. House Bill 132 (HB 132) seeks to resolve this issue with a simple but impactful amendment, making it easier for the state to verify eligibility for expungement. If passed, HB 132 will eliminate the need for extensive manual searches and ensure that more people receive the relief they deserve without unnecessary delays. Expunging non-conviction cannabis-related arrest records is not just about clearing data from government databases—it’s about removing barriers to employment, housing, and other opportunities that so many individuals struggle with due to the collateral consequences of their records. The pilot project and HB 132 are part of a broader movement towards automatic expungement. Twelve other states have already implemented some form of state-initiated expungement, recognizing that justice should not come with a price tag or bureaucratic hurdles. As a member of the Hawaiian Clean Slate Expungement Task Force , LPP will continue to explore expanding eligibility to include conviction records, and HB 132 will serve as an important foundation for further progress. "We are grateful to the Hawai‘i Legislature for recognizing the urgency of this issue and urge Governor Green to swiftly sign HB 132 into law. Together, we are making real progress in dismantling the harmful legacy of cannabis prohibition.,” said Adrian Rocha, LPP's Director of Policy. "We also extend our appreciation to Representatives Tarnas, Belatti, Grandinetti, Iwamoto, Kapela, Kusch, Lee, Marten, Perruso Poepoe, and Matayoshi for their support, the Hawai‘i Criminal Justice Data Center, the Attorney General’s office, the ACLU Hawai’i, Health Harm Reduction, Drug Policy Forum of Hawai'i, Doctors for Drug Policy Reform, Hawai'i Chamber of Sustainable Commerce, Council for Native Hawaiian Advancement, Hawaii Cannabis Industry Solutions, Marijuana Policy Project, and all stakeholders who have worked to ensure the success of this initiative." Let’s ensure that Hawai‘i remains at the forefront of meaningful cannabis justice reform. Tell Governor Green to sign HB 132.
By Stephen Post March 25, 2025
It is with a heavy heart that we share the news that Governor Youngkin has once again vetoed a critical cannabis justice bill. Despite overwhelming support from Virginia’s General Assembly, the governor has chosen to deny relief to thousands of individuals who remain incarcerated or under state supervision for cannabis-related offenses—convictions tied to laws that have since changed. Last year, Youngkin vetoed a similar bill designed by Last Prisoner Project (LPP), denying potential freedom to more than 1,844 people. This year, the legislature advanced two key bills aimed at providing relief. HB 2555 would have created a sentence modification process for individuals still impacted by outdated cannabis laws. Instead of signing this measure into law, Youngkin has once again chosen to uphold the injustices of the past. Luckily, the other bill, SB 1466, which will streamline state-initiated expungements for cannabis offenses, sealing ancillary records such as probation violations and failures to appear related to past cannabis charges, was approved by Gov. Youngkin, but will be sent back to the legislature with amendments. The Commonwealth should be concerned that the Governor admits cannabis is both the cause of and contribution to thousands of individual's criminal sentences but it is unwilling to adopt a solution to prioritize relief while preserving a commitment to public safety by vesting oversight throughout the process. The governor's office ultimately approved record relief for certain cannabis convictions, but for those behind bars, this administration has once again failed to deliver lasting change. LPP has been at the forefront of the fight for justice in Virginia. Our Director of Policy, Adrian Rocha, provided testimony in support of these bills, underscoring the urgent need to right the wrongs of cannabis prohibition. Additionally, LPP's Director of Advocacy, Stephanie Shepard, who herself served time for a cannabis offense, penned a powerful op-ed in Virginia emphasizing the necessity of these reforms and the human toll of continued incarceration. Virginia ended cannabis prohibition in 2021, yet many remain incarcerated for offenses that are no longer crimes. The Virginia Department of Corrections reports an average annual cost of $33,994 per incarcerated individual, while Virginia has generated over $8 million in tax revenue from medical marijuana as of 2023. HB 2555 was a crucial step toward justice—one the Governor has now denied. The governor’s decision ignores the will of the people and the reality that cannabis reform is not only necessary but overwhelmingly popular. Polling shows that 84% of registered voters support releasing individuals incarcerated for offenses that are no longer illegal. With each veto, Youngkin chooses to leave families separated and lives needlessly disrupted, all while Virginia’s legal cannabis industry continues to grow and generate revenue. We want to extend our deepest gratitude to the advocates and organizations who have fought tirelessly for justice, including Marijuana Justice Virginia, Nolef Turns, the Virginia NAACP, NORML, the Virginia Student Power Network, The New Majority Virginia, and Rise for Youth. While this veto is a setback, it is not the end. The fight for cannabis justice continues, and LPP remains committed to ensuring that no one is left behind. We will not stop until every cannabis prisoner is free.
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