top of page
  • Writer's pictureStuart Sheldon

I Enjoyed My time In Jail

A person who is nice to you, but rude to the waiter, is not a nice person.                                                                                             Dave Barry

I enjoyed my time in jail.

I was the only guy in tennis whites of the 50 burly thugs in my cell. Clearly not the best jail look.

I’d been arrested with my brother Eric for scalping tickets at a tennis match we were about to attend with my mother on Key Biscayne. When we didn’t show up, she thought we were bonding with a long walk on the beach. Next thing I know I’m wriggling to get comfy in the back of a sweltering squad car with hands cuffed behind me. No luck there. Down at the station, I got the whole shebang: fingerprints, mug shots, then a holding cell with a life-sentenced murderer waiting for his 4th parole hearing. “Can I have your address? I’d really like to write to you?” my pen pal killer asked. “Um, let me think about it.”

Cell doors have that unmistakable clank we all know from TV. So now we’re officially “inside.” Curiously, the 1st thing we were ordered to do was take a shower in an open wash area. Not sure why I needed a shower, but as I lathered up, decades of “don’t drop the soap” quips rang in my head. Next, they fed us cafeteria food on pale yellow kindergarten cardboard trays. I later learned the food had saltpeter in it to tamp down our sex drive, which was quite necessary given how horny the scene was making me.

The cell was large with a long row of bunk beds. Ours stood smack in the middle of a cluster of petty criminals trading war stories. “When my old lady got a restraining order on me, I hired my friend to beat her ass,” one nice fella bragged. Another spoke about getting shot in the leg. “Well, I was at the tennis matches with my mom, and there was a bit of a misunderstanding with the police officer…” Nooo, I kept my mouth shut tight and just listened.

As a fairly coddled middle class kid from the burbs, I learned from my short stay in the pokey (it was just one night and the charges were dropped). Frankly, I cherish the experience. I’ll never forget laying in my bunk staring at the bent springs of my brother’s bed above and listening intently to a slew of ass-kickers take turns elaborating on breaking and enterings, DUI, assaults and scams. It made crystal clear how privileged my tennis tournament reality is.

Those who know me, understand that my life is devoted to finding utopia. Seeking the brightness in people. Eavesdropping on those disenfranchised dudes in the Dade County Jail 20 years ago enhanced my quest. Some of those gentlemen were downright articulate. Poetry in their story telling, even if the stories were grotesque. For some, the steady three hots and a cot jail provides is a helluva lot more than they get on the street.

Share this:

2 views0 comments

Recent Posts

See All


Rated 0 out of 5 stars.
No ratings yet

Add a rating
bottom of page