Exactly 101 years ago, a chestnut colt named Sir Barton pranced to the post at Belmont Park for a chance to make history. Fresh off of his victories in the Kentucky Derby, Preakness Stakes, and Withers Stakes, he was primed for a tremendous performance. Twenty-five thousand racing fans perched on the edge of their seats, squinting at the distant colt and his two competitors, eager to witness a stunning display of speed from the unlikely star. In that moment, what the spectators didn’t know was that it was a miracle that Sir Barton was there at all.

Inauspicious Beginnings

Sir Barton began his life in Kentucky as the son of Star Shoot and Lady Sterling. Bred by John Madden, one of history’s greatest Thoroughbred breeders, Sir Barton spent the majority of his youth in his blind mother’s paddock. There, he had no opportunity to socialize with other foals and was further hampered by tender feet, increasing his notoriously bad temperament. He refused to extend himself in workouts unless challenged and had an intense dislike for most of his handlers.

Becoming a racehorse did nothing to improve his temper. Running greenly in his first race, he finished fifth, thoroughly beaten and outclassed. One month later at Saratoga, the horse now nicknamed “Sammy” came ninth in the Flash Stakes, more than 15 lengths behind the swift Billy Kelly. In the next 13 days, he started twice and lost by a total of 35 lengths. These lacklustre performances quickly convinced Madden to sell his colt.

Surprisingly, he soon had an offer from one of racing’s greatest owners: the Canadian millionaire Commander J.K.L. Ross. At six feet tall and over 200 pounds, Commander Ross had a larger-than-life personality. A football player and avid sailor, Ross had inherited tens of millions from his father in 1913. Following this, he engaged in philanthropy, founded a powerful racing stable, joined the Canadian Navy, and earned the Order of the British Empire for his service.

Hungry for even more success, he pursued the, “great splash of daring in his nature,” on the racetrack. He already owned Billy Kelly, but he saw promise in Sir Barton and purchased him from John Madden for just over $10,000.

Ross introduced the colt to his new trainer, H.G. Bedwell, a harsh horseman known as “Hard Guy.” He may have been rough, but he knew his horses. In an attempt to ease the pain in Sir Barton’s feet, he put piano felt between the horseshoes and Sir Barton’s hooves. However, Sir Barton was no fonder of Bedwell than anybody else – once even chasing Bedwell into a tack room in a fit of rage.

After the move, Sir Barton finished 16th in the Hopeful Stakes, beaten by the precocious Eternal. On his next outing he finally proved himself by running second in the Futurity Stakes. “Though Sir Barton had failed to win,” Ross’s son remembered, “[Commander Ross] seemed more pleased with the result than I had ever seen him.”

Days after this first glimmer of promise, however, Sir Barton contracted blood poisoning, becoming seriously ill. He barely survived.

A Derby Wager

While Commander Ross had been impressed by Sir Barton, he was still depending on Billy Kelly to win the next year’s Kentucky Derby. That winter, an unassuming stranger sidled up to Commander Ross and asked him if he wanted to wager with him on the Kentucky Derby. The stranger asserted that Eternal would finish ahead of Billy Kelly. Ross asked the man how much he was willing to bet and was shocked when the man suggested they wager $50,000 (over $800,000 today!). He was even more stunned to learn the stranger was none other than Arnold Rothstein, an infamous racketeer. Ross agreed to the wager, intending for Sir Barton to push the pace, exhaust Eternal, and hand the win to Billy Kelly.

When the time came, Sir Barton, Billy Kelly, Eternal, and nine others walked to the starting post. Sir Barton burst into the lead with Eternal chasing behind, followed closely by Billy Kelly. In the home stretch, Eternal faded and Billy Kelly overtook him.

Sir Barton after his Kentucky Derby win. While journalists as early as 1923 began using the term ‘Triple Crown’ to refer to the three races, it was not until Gallant Fox won in 1930 that the term became commonly used.
(Keeneland Library Morgan Collection – This image is protected by copyright and may not be reproduced in print or electronically without written permission of the Keeneland Library.)

Aboard Sir Barton, jockey Johnny Loftus realized that his mount was still going strong. He thumped Sir Barton with the whip and the horse exploded, leaving Billy Kelly in his dust. Hurtling under the wire, he had beaten Billy Kelly by five lengths.

Four days and 650 miles later, Sir Barton traveled to Pimlico for the Preakness Stakes. Yet again, he blew past the others and won. Afterwards, Bedwell entered Sir Barton into the Withers Stakes and the colt managed another win. Bedwell knew what his next target was: The Belmont Stakes.

On June 11th, Sir Barton, Natural Bridge, and Sweep On trotted to the post in pursuit of over $10,000 and a shot at immortality. Sir Barton’s energy was palpable. As soon as the bell rang, he surged out of the gate, fighting to gain momentum. Loftus pulled him back and he fell into second, tracking Natural Bridge.

The crowd watched breathlessly as they disappeared behind a clump of trees. Upon reappearing, Natural Bridge led Sir Barton by two lengths. Loftus gave Sir Barton his head and the colt hit his stride. He slashed Natural Bridge’s lead to nothing and thundered past.

Coming into the home stretch, Sweep On overhauled Natural Bridge and tried to hook Sir Barton, but he continued to draw away. Impossibly outmatched, Sweep On fell further and further back while Sir Barton widened the gap. Sir Barton galloped across the line, leading the others by five lengths and pulverizing the American speed record.

As the crowd roared its approval, Commander Ross and Loftus basked in their praise. Loftus turned Sir Barton around and led him to the winner’s circle and into history.

It would be more than a decade until the implications of his feat were known, but the colt had just become the first-ever winner of what would become known as the American Triple Crown.



Andrew Hanna is a high-school student who is currently working on a biography about Citation, the 1948 Triple Crown winner.