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The Season for Second Chances

Second chances, redemption, and renewal are important themes of the holiday season (especially in so many made-for-TV holiday movies!). I have my own story of second chances and renewal that I’d like to share with you.

In the late 90’s as a teenager in Florida I created a lot of financial trouble for myself. This is a lengthy story for another time, but in short I wrote many bad checks and handled credit cards poorly as a teenager. Eventually this resulted in multiple warrants for my arrest.

Facing the Music

Finally deciding to try to recover my life and mend my ways, one evening in early December of 1999 I voluntarily turned myself in to the county Sheriff’s Office in my hometown of Tallahassee, Florida. After being checked in, my possessions inventoried, showering with a complete lack of privacy, and given a set of itchy cotton clothes, I was now inmate #120336.

As a non-violent offender, I was soon placed in a relaxed area of the jail laid out in a single large room with dozens of bunks beds around a central common area. Although I was pleading guilty I couldn’t make the $10,000 cash bail, so I spent my time awaiting trial and sentencing there. An early breakfast by 6am, card games in the morning, then lots of reading in the afternoon in the same plastic green chair became my daily routine. The biggest shock I had to overcome was using the showers and toilets without any privacy – everything was out in the open with no doors, walls, or even curtains.

While incarcerated I met some interesting people – including a guy who had a prior arrest for blowing up public golf course equipment with homemade explosives and another guy who was an encyclopedia of jokes who had been arrested for selling gasoline out of cannisters on the side of the road.

Lessons Learned

One surprising issue was I had to pay for medical procedures while incarcerated. Even requesting a visit by the medical staff cost money that came out of one’s “Canteen”, which was also how an inmate paid for extra food, additional clothing, and amenities. Technically any “true emergency” would be free. However, considering that during my time I once ran a fever that caused hallucinations, and at a later point developed an infected tooth that had to be removed and was charged from my Canteen both times, I learned “true emergency” was an awfully high bar.

My public defender was obviously overworked, but they were always prompt and managed to process my cases in a timely manner. I also received deposited Canteen money and mail easily. But I noticed that many fellow inmates were having very different experiences. Others frequently had their court paperwork lost, were never informed of key dates, or had incoming money go missing. They were also often charged and sentenced with maximum punishments for non-violent crimes far more benign than mine, whereas I was quickly offered a plea deal to remove my felony charge and was granted “time served” for a quick release. I saw that the vast majority of the inmates experiencing issues were people of color. This was when I first realized the severity of racial disparities that exist in most judicial systems across the country and it led me to become an advocate for police and criminal legal reform.

My Recovery

I don’t regret my few months in jail. I had an easy time there and it gave me the much-needed time for introspection and to contemplate how to become a better person. After fully co-operating, pleading guilty to all charges, and not causing any disciplinary problems while in jail I was released with a little under four months of time served, probation, and a court mandate of full restitution (paying back all debts and fees to companies, banks, and the government).

I then spent the next many years of my life with a newfound work ethic, dedicating myself to paying back the more than $50,000 in debts and fees on minimum wage jobs – at one point having five part-time jobs at one time (!!) with 68 days of continuous working without any time off.

I hope you’ve appreciated this personal story of a formative time in my life. If you do, then please give some appreciation to your local Public Defenders office – they do incredibly hard work that is critical for our society. Also take a moment to learn about “Restorative Justice”, which can go a long way to improving our criminal justice system and community.

This is an early-access story from Theo that was exclusive to subscribers of the campaign’s email list a few days before it went up on the website.