PEE-WEE

Tom Calarco
5 min readNov 27, 2023

How did I get myself into this?

Pee-Wee, AI Art by Tom Calarco, generated thru NightCafe

I was still trembling. I had been holding in my terror for hours. I had left my home in upstate New York about a week earlier, my sights set on Hollywood, where I had lived seven years earlier for two months.

I did dumb things when I was in my 20s. I had so much faith in human nature and assumed everyone had some goodness; even still, though now I am much more guarded.

I had picked up this big black dude, hitchhiking and looking forlorn outside Vegas. He was dressed in a sweatshirt and jeans, and really big, a six-foot version of Shaq, easily over 300 pounds. I’d say he was about 30 years old, maybe a little older. He smiled as he got into the passenger seat, his eyes wide open with gratitude.

He was friendly and cordial. He appeared quite happy that I had picked him up. He said he had been standing there for hours without anyone stopping. He was going to LA, where he was from. I told him I could drop him off in Hollywood, and he said that was cool, that he could get home from there.

It was about 300 miles down the road to LA, so I was going to have a co-pilot on a long ride. I’d been on the road for a long time, so having someone to ride along seemed like a good idea. He told me they called him Pee-Wee. He laughed when he said this, and so did I.

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Tom Calarco

One of the nation’s foremost experts on the Underground Railroad, Tom has written eight books about the legendary network — see undergroundrailroadconductor.com