How A Mobster’s Bet Led To Horse Racing’s First Triple Crown Winner

Sir Barton at the 1919 Preakness

Photo: Wikimedia Commons

Sir Barton would have never became America’s first Triple Crown winning horse if it hadn’t been for a bet between the horse’s owner and mobster Arnold Rothstein.In an LA Times blog post today, Brian Cronin reveals that before the 1919 Kentucky Derby, Rothstein bet JKL Ross that Eternal would finish ahead of Ross’ horse Billy Kelly.

The loser would pay the winner $2,500 so long as one of the horses came in the top-three.

But Ross had an advantage. He owned a second horse, Sir Barton, that was scheduled run in the Derby.

Ross instructed Sir Barton’s jockey to run the horse as hard as he could out of the gate in order to set a fast pace. Ross thought Eternal would get caught up in the pace, lose his energy, and eventually fade as a waiting Billy Kelly finally made his charge.

However, things didn’t go as planned.

Sir Barton fired out of the gate, but instead of getting worn out and falling back, the horse kept up the pace and eventually won the race going away.

At the end of the day, Ross was the big winner. He won his bet with Rothstein when Billy Kelly came in second place. And he discovered that Sir Barton was much stronger than he previously imagined.

The horse went on to win both the Preakness and the Belmont.

If Ross doesn’t make the bet, he never tells Sir Barton’s jockey to fly out of the gate, the horse doesn’t win the Derby, and the entire course of American horse racing is changed.

Check out Cronin’s full version over at

Business Insider Emails & Alerts

Site highlights each day to your inbox.

Follow Business Insider Australia on Facebook, Twitter, LinkedIn, and Instagram.