Did a side bet lead to horse racing’s first American Triple Crown winner?

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HORSE RACING LEGEND: A side bet inadvertently led to the first American Triple Crown winner in horse racing history.

Due to his being a character on the popular HBO program, Boardwalk Empire, early 20th Century mobster Arnold Rothstein has become a well-known name again (not that he ever was obscure, of course). However known or unknown he was by the general public, though, he has always been a bit of a legend in the world of sports gambling. For decades (nearly a century now!) people have debated over exactly what role he played in the infamous 1919 Black Sox scandal. At the very least, he knew that a group of Chicago White Sox players had been paid to throw the 1919 World Series against the Cincinnati Reds and he profited greatly from that information. At most, he financed the entire operation. I tend to believe that the latter assertion is closer to the truth of the matter. In any event, while his involvement in baseball gambling will likely be his sports gambling legacy, Rothstein was actually far more interested in horse racing.

Not just gambling on horse racing, though (which he did plenty of) or fixing horse races (which he also did plenty of), but Rothstein just plain ol’ enjoyed horse racing period. He would often attend races with his wife, Carolyn, especially at Belmont Park (as Rothstein ‘worked’ in New YorK). While he would bet remotely if he couldn’t be at the track, he preferred being there for the live events. Over time, he began to fancy himself a bit of an expert on horses. And what better way to express this expertise than by gambling? This led an amazing bet between Rothstein and a horse owner, John Kenneth Leveson (JKL) Ross, which inadvertently set the stage for the first horse to win the American Triple Crown.

How did it happen and is the story actually true? Read on to find out!

JKL Ross was born to one of the co-founders of the Canadian Pacific Railway, so when Ross’ father passed away in 1913, Ross inherited sixteen million dollars! Two years later, Ross entered the world of Thoroughbred ownership and breeding. He hired jockeys Earl Sande, Carroll Shilling and John Loftus as well as trainer H. Guy Bedwell. All four of those men are currently enshrined in the United States Racing Hall of Fame, so Ross definitely knew how to pick his employees. He also seemed to know how to pick horses, as one of the first horses he ever bought, Damrosch, won the 1916 Preakness Stakes!

Thus we come to early 1919 and the months leading up to the forty-fifth running of the Kentucky Derby in May of that year. Ross was eating dinner in a Manhattan restaurant one day when he was approached by another gentleman. He wanted to make a bet with Ross on the upcoming Derby. Ross later recalled that he expected the bet to be for $100 or something like that. Instead, the bet was for $50,000 (I’ve seen the story told differently - some say $20,000 and some say $50,000 - the $50,000 version appears to be more common - it’s hard to say which one is more accurate). It was right around this point that Ross realized that he was dealing with Arnold Rothstein.

The bet was this - Rothstein would bet that Eternal, a horse owned by James W. McClelland, would finish higher than Ross’ horse, Billy Kelly. The catch was that the winning horse would have to place in the race (finish first, second or third). So, entering the race, Ross had a clear strategy. He had two horses running in the race. Jockey Earl Sande was given the choice of which one to ride. He chose Billy Kelly, leaving the other horse, Sir Barton, for fellow Ross jockey Johnny Loftus. The strategy was that Sir Barton would be the ‘rabbit’ - he would run strong early to dictate a fast pace, wearing out the other horses and then fall back at the end to allow his fellow horse, Billy Kelly, to win the race.

However, all Ross really needed was for Billy Kelly to finish ahead of Eternal and to place. Eternal had a tough go at it that day (some folks believe that the wet track was his undoing) so he was quickly out of it. So it soon became apparent that it was going to be either Sir Barton or Billy Kelly. Interestingly, Sir Barton’s trainer, the aforementioned Bedwell, had bet on Sir Barton to win. Whether that was just an informed guess or whether he knew what was about to happen, Bedwell’s bet proved prescient, as Sir Barton did not slow down as originally planned. Loftus would later recall, ‘I stood up in the stirrups and looked around to see where Sande and Billy Kelly were’ and that ‘[s]seeing nothing of Billy Kelly, I gave Sir Barton a cut of the whip and he jumped off as if it were the start. Then I rode him the rest of the way, figuring to hell with Bedwell, Sande and Billy Kelly.’ Since Billy Kelly was close behind Sir Barton most of the way, Loftus’ story seems a bit suspicious, as it seems he more likely just decided ‘to hell with them’ and went to win it. Of course, little did he know that Bedwell had bet on his horse to win (maybe Bedwell knew Loftus’ personality that well?).

In any event, Billy Kelly placed second (the first time the same stable had the top two finishing horses) and Ross collected $20,825 for Sir Barton winning the race, $2,500 for Billy Kelly finishing second and $50,000 for Billy Kelly defeating Eternal.

This story is, in and of itself, pretty cool, but what makes it even cooler is that Sir Barton then went on to win the Preakness Stakes, the Withers Stakes and, to complete the first American Triple Crown (before the term even existed), the Belmont Stakes. Had he not served as a rabbit in the Kentucky Derby, there is a very good chance that the horse would not have won the Derby and thus, would not have won the Triple Crown. So his success really did appear to be owed to, of all things, a side bet between his owner and a mobster.

So as for the truth of the legend....

STATUS: True.

Thanks to Jim Bolus’ Remembering the Derby and Kentucky Derby Stories, Dorothy Oars’ Man o’ War: A Legend Like Lightning and David Pietrusza’s Rothstein: The Life, Times, and Murder of the Criminal Genius Who Fixed the 1919 World Series for the information on this story!

Thanks to reader Terry Crow for suggesting that I feature this legend!

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