Conning the Con Men of Kentucky

Two college boys hitchhiked 1,000 miles to Louisville, drank freely (and free), sneaked into the Derby—and even got to see the race.

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  1. First I made a sign. I bought a roll of red tape that was supposed to glow in the dark. I cut the tape into strips and made letters on a white cardboard square: KEN. DERBY.

    “That’s not how you abbreviate Kentucky.”

    “Sure it is.”

    “No, it’s k-y period; not k-e-n.”

    “People will know what I mean.”

    I left Worcester, Mass. at 1 o’clock the next afternoon, a Thursday. It was cold and there was rain. I got a quick ride the four miles to the entrance of the turnpike. Then I stood for a long time in the rain, holding the sign across my chest.

    A car stopped. The driver leaned across the seat.

    “Who’s Ken Derby?”

    “Nobody. This means Kentucky Derby. That’s where I’m going.”

    “Oh. I thought you were promoting some politician.” (There was a primary in Massachusetts that year.)

    The car pulled away. I threw the sign into the weeds. Five cars later I had a ride to Hartford.

    * * *

    The first track Larry and I ever snuck into was Yonkers, when we were 15 years old. It was easy because the guards were old men and we outran them. Larry’s father was a $2 place cashier in the grandstand. He would give us the horse early, and we would hop over another fence into the clubhouse and run around begging quarters and dimes until we had enough to bet it. Once we asked Jackie Robinson for a quarter. He said no. Occasionally the horse would win and we could bet our own money for a while. We snuck into Yonkers so much that the next summer they put a sign on the barbed wire that said, “Dang...