Gangrey
Vol. I · No. 1Prolonging the Slow Death of NewspapersEst. 2026

The Misadventures Of Tom Sawyer

Lane DeGregory: Tom Sawyer is in jail.

Again.

He's well known at the Hillsborough County lockup: trespassing, drinking in public, resisting arrest. Alkie crimes. It's petty stuff, but the record fills 83 pages. And that's just in Florida, since 1993.

At 77, he's one of the oldest guys in the Falkenburg Road Jail. In his mug shots, he's always wearing overalls. Sometimes his thin chest is bare beneath the dingy denim. Sometimes he wears an undershirt. But always, those overalls — except, for some reason, in the most recent booking photo.

The other day I went to see him.

"You want to talk to me?" he asks, shuffling into a holding room. "Why?"

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