Born on the 1st Saturday in May

I didn’t just show up on May 2nd. I arrived with hooves thundering in the background.

The 79th running of the Kentucky Derby at Churchill Downs provided a dramatic soundtrack for my birthday. Between the starting gate and the finish line, I made my entrance into the world. Timing, as I would later learn, is everything, especially if you’re betting on it.

My dad, meanwhile, had money riding on the favorite, Native Dancer. This wasn’t the polished, app-based gambling world we know today. No sleek interfaces or “deposit bonus” nonsense. 

This was Cheyenne, Wyoming, where a guy would stroll into local businesses like he was delivering office supplies, except he was taking bets. Completely illegal but completely trusted.

Dad also dabbled in Irish Sweepstakes tickets, which were as legal as robbing a bank but with better branding. I don’t recall him ever hitting it big, but that never seemed to matter. He was a gambling man in the purest sense, not chasing riches, but the action and the thrill.

Then came the race. On the left is a photo taken on May 2, 1953, of Dark Star in the winner’s circle.

Native Dancer looked like a sure thing. If there’s one thing horse racing stories have, it’s a good plot twist. Dark Star, a longshot with a name that sounds like a rejected Batman villain, surged at the wire and won by a neck.

Just like that, my dad lost his bet, and just like that, I was born into a world where the favorite doesn’t always win.

That’s a fitting origin story.

By the time I turned 19, the legal drinking age at the time, Kentucky Derby Day had officially leapfrogged Christmas as my favorite holiday. Mint juleps replaced the tree and presents.

Back in the day, before gambling went respectable and crossed state lines, I had to work for it. I tracked down off-track betting joints, like the Stampede in Aurora, Colorado,  like a guy following a treasure map. I walked in, placed a bet, grabbed a drink, and for two minutes I was a part of the race action.

These days, I’ve scaled it back. On my birthday this year, the bookie and my upstairs neighbor, Lindy, organized a casual race pool. This year I drew the 22 horse, Ocialia, that showed and won $3. The ritual hits the same. 73 years later. The call to the post, the crowd, the faint hope that I drew the winning horse.

If my Kentucky Derby birthday taught me anything, it’s that favorites are comforting, and longshots are interesting. Life has a funny way of siding with the Dark Stars of the world.