News, Views, Happiness Pursued

Shining Light on Humanity

by | Oct 2, 2020

By this time next year, I could be dead. Never again to see the ocean or feel the coarse bark on a maple tree, smell the crisp scent of pine needles as they cushion my steps in the woods, or curl up on the couch with my lady and a movie of her choice. These are some simple pleasures, the quiet moments I miss as I ponder my inevitable demise.

Some may think it morbid that I live comfortably with the end of my life. Yet, it was only when I began to think beyond death that I began to truly appreciate life, to be thankful and purposeful with each day that God chooses to wake me up. It began when my mentor, E, challenged me with the question: “What kind of legacy do you want to leave?”

I was 22 years old, and he was asking me, “How do you want people to remember you when you die?”

“What?!” I couldn’t comprehend the necessity of the question. But, as time passed, I came to realize that I have a say in how people will remember me. The media coverage of my crime and imprisonment does not need to be my legacy. With God’s help and guidance, I can infuse my immediate surroundings with life and hope every single day.

I didn’t reach this conclusion once and for all. There were many times I came very close to succumbing to the sweet siren song of complacency. Just giving up, falling in line, and letting this prison become my entire existence. Oh, how easy that is to do! I didn’t understand that if I gave in to that temptation I would be dooming myself to a life in prison — even after my eventual release. Because that is what prison does to the unsuspecting lawbreaker. That is what prison is designed to do.

As Robert “Bobby” Dellelo, a co-author of When The Prisoners Ran Walpole: A True Story in the Movement for Prison Abolition, says in that book’s closing chapter, “For the most part, individuals leave the [prison] system less able to maintain their lives with dignity than when they came in.” The few like me, who have rehabilitated ourselves, are the exception to this rule. So many more hear that sweet melody and fall right in line. They follow the rules — either those established by the prison or those instituted by the prisoners — and effectively hand over their lives to the System.

What many hardworking taxpayers in Maine and throughout the country don’t know is that they’re paying to keep the recidivism rate high and the prisons full, while also keeping communities unsafe. That’s because most people who come to prison buy into the belief that this is it for them — they will be forever trapped in the System. Even before their release, they start preparing for their next prison bid. Sadly, this belief (based largely on society’s unwillingness to forgive and accept them back into the fold) becomes a self-fulfilling prophecy.

This is why we need taxpaying citizens to demand their money be spent on rehabilitation and the safe reentry of incarcerated people to society. We need business owners to learn about the Federal Bonding Program and other incentives to hire people who wear the brand felon (check out Bob Pelshaw’s fact-based “Ten Bottom-Line Reasons to Hire Ex-Felons” and other work at We need state lawmakers to stop fighting against reform initiatives and voters to support the legislators who introduce them, like Reps. Rachel Talbot-Ross, Jeffrey Evangelos, Pinny Beebe-Center and William Pluecker (among others). We also need more bold, progressive elected officials like District Attorney Natasha Irving.


My eldest nephew has now turned 22. I challenged him with the same question E posed to me: “What kind of legacy do you want to leave?” And now I present you with the same challenge. No matter your age, it is never too early, or too late, to start building your level of comfort with death. It’s OK to acknowledge your mortality and embrace it. Once you do, you’ll find life more fulfilling. This isn’t some clichéd exhortation to live each day as if it were your last. This is a call to purpose.

As the events of the past several months have taught us (if we’ve cared enough to learn), the time for living on the sidelines is over. Now is a time of engagement. If you’re living a life that doesn’t line up with that purpose, it’s time to make a change — study more, ask more questions, switch jobs or even careers if necessary.

No, it probably won’t be easy. No, it may not be popular. But yes, it is necessary. Please, kick complacency in the backside and get moving with life!


Leo Hylton’s sister, Rosie, is organizing a fundraising campaign to cover tuition expenses for Leo’s pursuit of a Master’s degree via George Mason University. Click here for more info and to contribute

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