2026 Kentucky Derby Betting

My First Kentucky Derby Bet

By the US Racing Team

I remember placing my first bet at the Kentucky Derby online.

It was in 2005, and I decided to bet on a horse called Giacomo being ridden by Hall of Fame jockey, Mike Smith. Giacomo was certainly not a favorite.

What were the odds? 50-1. Yes, the same Kentucky Derby Odds as Mine that Bird who won in 2009!

The only horse with worse odds who won the derby was Donerail who started at 91-1! So, odds don’t tell the full story with the horse and jockey who end up winning the garland of red roses in Lousiville.

Anyway, Giacomo was named after the singer Sting’s son. Jerry Moss was the owner - Jerry Moss and Herb Albert (yes, of the Whipped Cream and Other Delights!) were the founders of A&M Records. Sting performed and recorded under that label as a solo act and also when he was in the rock group The Police.

Giacomo is Italian for James. Ironically, Giacomo has a half-brother named Tiago which in Portugese means James!

But, I digress. . .

So, why did I bet on Giacomo at that year’s Derby?

Let’s put it this way: I’m a sucker for the underdog. If there was a horse called Rocky, I would have bet on him based on principle.

I didn’t bet on Charismatic at the 1999 Kentucky Derby (I would have if I was there- he was a long shot, too—31-1 odds) but I bet on Lemon Drop Kid at the 1999 Belmont Stakes.

It’s not that I wasn’t on the Charismatic bandwagon—I wasn’t a Triple Crown hater.

I bet Lemon Drop Kid because my sister loved lemon drops (I think it was the Cosmopolitan drink of ’99 before Sex and the City ushered in Cosmos). I wasn’t following racing back then—I didn’t know Chris Antley’s story and Charismatic’s, either.

So, now the Derby is coming close. The first Saturday in May, it’s easy to remember. And it always takes place at Churchill Downs.

I hope that if you are betting on the Kentucky Derby for the first time you will consider a long shot. Bet for the underdog. Sometimes, he may not have fleas. Sometimes, he might just rise to the occasion. And sometimes. . . just sometimes, a 50-1 long shot will put a bankroll in your pocket!

Good luck with your bets and everybody at US Racing hopes you pick a winner! (If you happen to lose, we wish you have an extra mint julep at arm’s length.).