Completing My First Life Sentence: Why Does it Matter?
This July marks the completion of my first life sentence. After 18 years and 10 weeks, I’ve lived my entire life over again behind prison walls — year for year, month for month, day for day. More than a figuratively new creature, I am literally a whole new human being. If all the cells in a human body are replaced every seven years, I have been remade more than twice since my freedom was relinquished to the State of Maine.
So what, though? Back then, as a newly incarcerated teenager, I devised this grim milestone to replace the rites of passage my peers outside the barbed wire were anticipating, like attending and graduating from college, renting an apartment, starting a career, getting married, buying a home, having a child. I’ve been anxiously awaiting this day for years, expecting some new feeling, some shift in consciousness, some revelation. But its arrival now feels anticlimactic, if not wholly disappointing.
Now that my time on this earth has doubled, I want to openly reflect on the world I left and who I was at that time; the world of today and who I’ve become; how I became this new person; why my story matters; and what readers of this column can do if you’re inspired to use my story to make a difference.
I was a deeply wounded child masquerading as an implacable man when I entered prison in 2008. Maine’s minimum wage was $7.25 and the Motorola RAZR was all the rage. The U.S. hadn’t yet experienced a Black president, and Black lives wouldn’t start to matter for another dozen years.
I had just reached the legal age to smoke and vote, but I only believed one of those things was worth doing. It took me less than an hour to make enough money to buy a pack of Newport shorts, which then cost just over $5, and politics was the business of old white folks who didn’t have to struggle to survive. My worldview was small and twisted up by many and varied childhood traumas, so I was both unsafe in how I navigated my surroundings and ignorant of how little I could actually control. I didn’t know how quickly or easily I could lose control over my own actions.
Today, I watch the news, talk with my family, and learn from outside colleagues that this country is more polarized and prepared for impromptu eruptions of interpersonal and intergroup violence than during almost any other period since the Civil War. Politics are so deeply divided that family members and best friends lose their ability to be kind and empathetic upon the first mention of certain topics or elected officials.
Maine’s minimum wage has more than doubled since 2008, to $15.10 an hour. Smartphones are in the hands of small children, cigarettes cost more than $15 a pack, and the legal age to smoke is now 21, as state lawmakers have since determined that youth ages 18 to 20 are not mature and responsible enough to make rational decisions regarding tobacco use.
I have zero interest in ever smoking again, but I now vote consistently and have been involved in writing and advocacy around legislative bills for almost 10 years. I navigate fraught political conversations with care and respect, and I work daily to build peace inside, outside, and across prison walls. I am safe in how I navigate the world, I remain acutely aware of how little of it I can control, and I am vigilant about the intent and impact of my behavior — both in speech and action. Transforming from a fragile and unsafe young person into a steady and safe adult has been a long, painful, beautiful, messy process.
That process began with the words of those I harmed. I lost everything when I went to prison, but I never let go of the victim impact statements from my sentencing hearing.
It’s true that, in the interest of self-preservation, I buried those papers for years after first reading them, but I kept them. Every few years I’d take them out and try to read them again, but most times I failed. It hurt too much. I was still too ashamed. I lacked the full mental, emotional and spiritual wherewithal to allow my mind, heart and spirit to be penetrated by their words without shattering. I was too weak to see their faces and feel their pain and rightful rage. I wasn’t ready to honor them in the ways I am obligated to honor them by my harmful actions.
It took almost 12 years to heal enough to again be able to read the statements of the people I harmed and their family. Over that time, I had relinquished my fate to a loving Gd by withdrawing my petition for any post-conviction review of my sentence, and instead settled in to either live or die in prison.
I received loving support, guidance, mentorship, and formal and informal education from incarcerated elders, outside volunteers, college professors, and prison staff and administrators. I journeyed inward to understand why I’d caused the grievous harm I did. I have become a tutor, mentor, confidant, caregiver, program facilitator, barber, professor, and leader in my inside and outside communities. I have grown into an adult who carries himself with dignity and respect for others and for himself.
It was during this past year of personal loss and constant upheaval — the last year of my first life sentence — that I became truly still in the knowledge that HaShem is Gd (Psalm 46:10). I sat again with those victim-impact letters, helpless to change the past, incapable of easing the suffering or mending the broken hearts or bodies of those I hurt. Finally, I did not flinch or shy away from the truth. With tears in my eyes and heart, I bowed my head in repentant reverence before the strength of their survivorship. With new ears I heard them, with a new heart (Ezekiel 36:26) I honored them, and I vowed to continue working to repair the world around them and prevent others from being harmed like they were.
Why does my journey matter? What good purpose does it serve for me to share my story in a public forum?
As I wrote here six years ago in “The Awesome Power of Forgiveness” (May 2020), I’m not a good person. I do not write for my own vain pursuits, nor for praise. If that were the case, I would have stopped shortly after I began. For, while I am deeply grateful for the affirmations and encouragement I have received from a handful of readers over the years, I have tasted far more venom than honey for my efforts. This is true from both sides of the walls, and from the lowest to the highest levels of institutional and social hierarchies.
My story and the lessons I share from it matter only insofar as they help reduce the amount of harm that happens all around us every day. Part of this work is asking people to see incarcerated individuals as whole human beings worthy of dignity and respect, and worthy of the support and opportunity to repair the tears we made in the social fabric of our communities. I ask that you see our humanity, our ability to grow, and our potential to add value and safety to your town.
The good I’ve done, the growth I have attained, the accountability for my actions I hold — none of this is unique to me. I am not special. With the right care, support and guidance, many safe, steady, accountable people can be welcomed back into society to make it stronger, less fearful, less divided.
How can you use my story for the good of others? Pause here for a moment. What comes to mind? Write down that thought.
Some other avenues I suggest include:
• Write, e-mail and/or call your state and federal lawmakers to tell them you believe in second chances; ask them to support Second Chance and Fair Chance legislation; and encourage them to visit their local jail and prison to see the conditions and talk to both the incarcerated people and facility staff.
• Vote! Vote for lawmakers and political leaders whose actions support rehabilitation and second chances.
• Reach into your local jail and/or prison and ask administrators for permission to tour the facility; ask what volunteer opportunities exist (e.g., tutoring, reading and discussion groups, etc).
• Become a pen pal — join a reputable pen-pal site or reach out to Parole-4-Maine or the Maine Prisoner Advocacy Coalition to ask about connecting with people on the inside.
• Help reinstate parole in Maine. Visit parole4me.com for ways to get involved, and read my December 2025 column, “Addressing Parole Concerns for Maine Lawmakers,” for more background on where the movement currently stands.
• Share this column. Send it to at least two people you know; leave a copy in a public place; mail or e-mail it to a lawmaker or gubernatorial candidate.
As Fannie Lou Hamer famously said, “No one is free until we are all free.” I genuinely believe we have the collective power to envision and co-create a future that is both free and safe. Let’s take action together.
Leo Hylton is a PhD student at George Mason University’s Jimmy and Rosalynn Carter School for Peace and Conflict Resolution, currently incarcerated at Maine State Prison. His education and work are focused on Social Justice Advocacy and Activism, with a vision toward an abolitionist future. You can reach him at: Leo Hylton #70199, 807 Cushing Rd., Warren, ME 04864, or leoshininglightonhumanity@gmail.com.
