The $300 Roll
By the mid-seventies, the dust from the Hazelton commune days had settled, and I had moved on to a new chapter: running my own after-hours club. It was around this time that a mysterious, beautiful woman began appearing in the local orbit—haunting Club 22, The Pilot, and Grossman’s Tavern. I didn't recognize her at first, but it was Cayle Chernin, the actress who played Selina in Going Down the Road. She had just returned from a wild stint in Hollywood, having lived in the orbit of Dennis Hopper.
One night, she walked into my bar with a guy I took an instant dislike to. We ended up hunched over a table playing poker dice, and by the time the early hours rolled around, I had cleaned him out for about $300. We were both deep in our cups when he admitted he was flat broke.
"One more game," I said, half-joking through the booze. "You win, you get your three hundred back. I win, I get your girlfriend."
To my surprise—and Cayle's visible disbelief—he agreed. We rolled the dice, the sound clicking sharply against the wood i When the dice settled, I had won.
Cayle didn’t hold back. She went into a legendary tirade, laying into the guy for his arrogance and the sheer stupidity of putting her up as a stake. She told him to get lost right then and there. Then she laughed and grabbed my arm, she decided to "pay off" the debt.
We dated for a while, but what began as a drunken gamble evolved into one of the most significant relationships of my life. Beyond the romance, we became the best of buddies. Cayle was a powerhouse—an extremely brilliant writer, actor, and producer who never lost her spark. We stayed close friends until the very end; I was Skyping with her just a few days before she passed away. I miss her dearly. She was more than just a girl in a movie; she was a lifelong friend I won on a roll of the dice.

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