But none before Sir Barton had ever attempted, much less won, the premier stakes for three-year-olds held in the major racing centers of Kentucky, Maryland, and New York.

There was no model for Sir Barton’s success.

There, of course, had been a number of three-year-olds before him which had left a lasting imprint on the history of the turf, and to this day some would objectively be considered finer runners. But none before Sir Barton had ever attempted, much less won, the premier stakes for three-year-olds held in the major racing centers of Kentucky, Maryland, and New York.

Two thousand nineteen marks the centenary of Sir Barton’s entree into American turf lore, but even that wasn’t immediately apparent at the time. As is well known, the linking of the Kentucky Derby, Preakness, and Belmont Stakes into a cohesive series horsemen wanted to win came more than a decade later. The concept of an American Triple Crown was widely attributed to famed turf writer Charles Hatton and Sir Barton’s admittance into its pantheon was strictly retroactive.

In many respects, 1919 was also Year One for the Triple Crown as we know it, minus modifications for dates and distances. While decades old, the Kentucky Derby had only just begun to gain true acceptance from the sport’s Eastern pillars, largely stemming from Harry Payne Whitney’s exultation at his filly Regret’s victory in 1915.

The Preakness, which the Maryland Jockey Club acknowledged at the time only dated to 1909 (the so-called “lost Preaknesses” weren’t “discovered” until much later), was the proverbial new kid on the block, but by 1919 it was the most lucrative race for three-year-olds contested in the east with a purse of $30,000.

The Belmont Stakes, founded in 1867 and closest in equivalency to England’s Derby at the time, had long maintained its prestige despite lean years earlier in the decade when it was blacked out along with the rest of the sport in New York for a short time. However, its supremacy began to be seriously challenged from Kentucky and Maryland, where the existence of pari-mutuel wagering presumably provided an infusion of purse money the then bookmaker-dominated New York circuit could not immediately match.

A most unlikely pioneer

the timing seemed right for American racing to enter a new era

In other words, the timing seemed right for American racing to enter a new era, much like the world in general had following the previous fall’s armistice ending The Great War.

Sir Barton was a most unlikely pioneer. A roguish colt, he was a half-brother to Sir Martin, the beaten favorite in the 1909 Epsom Derby when he lost his rider around Tattenham Corner. Sir Barton raced four times – all in stakes – for co-breeder John E. Madden, who sold the underachieving son of Star Shoot to Commander J. K. L. Ross for $10,000 after Sir Barton failed to earn a penny in the Tremont, Flash, United States Hotel, or Sanford Memorial Stakes.

Ross, heir to the Canadian Pacific Railway, “purchased any likely looking runner he happened to see,” wrote William H. P. Robertson in “The History of Thoroughbred Racing in America.” His private trainer was Guy Bedwell, a seven-time champion trainer who had also been the nation’s leading owner in 1916 before dispersing his stable to work for Ross.

While Sir Barton struggled to prove himself any type of runner, the gelding Billy Kelly was a proven winner when Ross acquired him early in the 1918 Saratoga meet. A six-time winner in his first eight starts, he would win eight of his next nine races for Ross, including the Flash, United States Hotel, and Sanford Memorial that Sir Barton would lose by a combined margin of 50 1/2 lengths.

Sir Barton’s margin of defeat in his debut for Ross in the Hopeful Stakes is unknown, but it was significant. Eternal, who would go on to defeat Billy Kelly in the McLean Memorial at Laurel later in the fall, won by three lengths, with an eight-length gap between the second- and third-place finishers. Sir Barton came home 16th in the field of 20.

The one true sign of life Sir Barton showed as a juvenile came in his season finale when, re-outfitted with blinkers, he finished second in the Futurity Stakes over a straight six furlongs at Belmont Park. He missed the remainder of the season after developing abscesses caused from a kick by a stablemate. Thus, Sir Barton entered his winter quarters still a maiden but having recouped some of Ross’ investment.

Rabbit

The 1919 Kentucky Derby was held on May 10, with Eternal and Billy Kelly the horses to beat. Eternal had won his only prep at Oaklawn Park, while Billy Kelly had racked up two wins at Havre de Grace in Maryland. Strange as it might seem to modern eyes, Eternal, Billy Kelly, and Sir Barton, who did not prep at all, tackled the 1 1/4-mile Derby without having raced beyond six furlongs.

Eternal was the 2.1-1 favorite in the Derby, with the entry of Billy Kelly and Sir Barton at 2.6-1. While the historical consensus over the years has been that Sir Barton was more or less entered as a “rabbit” for the more accomplished Billy Kelly, a race-day news wire preview noted that:

“Billy Kelly is said to be at his best, but many doubt his ability to negotiate the Derby distance at top form. It is understood Sir Barton is the main reliance of the Ross stable.”

In receipt of a significant weight allowance due to his maiden status, Sir Barton broke on top, repelled challenges from both Eternal and Billy Kelly, and drew off late to win by five lengths under Johnny Loftus. The final time over a heavy track was a pedestrian 2:09 4/5. Billy Kelly finished second, making Ross the first person in history to own the top two finishers in a Kentucky Derby. The stable earned $23,325.

The 1 1/8-mile Preakness was scheduled just four days later. Forming an entry with Sir Barton was the filly Milkmaid, but she proved no factor as Sir Barton went to the front end again and won eased up by four lengths over Eternal. The 7-5 favorite, Sir Barton won under scale weight of 126 pounds in a time of 1:53 over a fast track and earned Ross another $24,500.

“Loftus says Sir Barton is the best horse he ever rode and this is a plenty, as Johnny has kicked many a good one in his time,” noted the Thoroughbred Record. That opinion undoubtedly changed months later when Loftus piloted through 10 wins from 11 starts a brilliant juvenile named Man o’ War.

In a move later repeated by Omaha, Whirlaway, Count Fleet, and Citation, Sir Barton made one start in between the Preakness and Belmont Stakes. Again facing his old foe Eternal, Sir Barton won the one-mile Withers Stakes at Belmont Park eased up by 2 1/4 lengths.

In the 1 3/8-mile Belmont Stakes on June 11, Sir Barton faced only two others. Indulging pacesetter Natural Bridge, Sir Barton seized the lead after entering the main course on a much differently configured Belmont track of the day and won comfortably by five lengths. The 7-20 favorite finished in 2:17 2/5, a new American record. The winner’s share was approximately half that of the Kentucky Derby and Preakness at $11,950.

“I only let him run an even eighth of a mile at the top of the stretch,” Loftus was quoted by Daily Racing Form, suggesting Sir Barton could have shattered the distance record by more if given the chance.

Sir Barton proved a very good horse if not an all-time great. He won four of his remaining nine starts at three, and in 1920 won four stakes in 12 starts. His most notable win that season was the Saratoga Handicap, in which he beat the famed gelding Exterminator by two lengths while giving “Old Bones” three pounds in track-record time of 2:01 4/5 for 1 1/4 miles.

Race of the Ages - Sir Barton vs Mano' War
Race of the Ages – Sir Barton vs Man o’ War on Nov. 2, 1920
(Wikimedia Commons / Educational Films Corporation of America / Educational Film Exchanges)

Four

Sir Barton’s most famous appearance as a four-year-old was in the $75,000 Kenilworth Park Gold Cup in Windsor, Ontario, a 1 1/4-mile match race between him and Man o’ War. Wagering reflected the ostensible mismatch as Man o’ War started at 1-20 with Sir Barton at 5.55-1. “Big Red” easily defeated the only older horse he would ever face by seven lengths. Sir Barton was retired after suffering two more losses at Pimlico, concluding his career with a record of 31-13-6-5, $116,857.

Sir Barton sired eight stakes winners, most notably 1928 Kentucky Oaks winner Easter Stockings. He ended his days in Douglas, Wyoming, where he died in 1937. His remains lie in a small community green called Washington Park.

Sir Barton’s feat and place in history is the subject of a soon-to-be published biography from the University Press of Kentucky, “Sir Barton and the Making of the Triple Crown” by Jennifer S. Kelly. A century after an initial underachiever eventually blossomed and planted the seed that would become American racing’s popular annual narrative, a fuller account of his life and significance seems most proper.

(Sir Barton and Johnny Loftus Photo Courtesy of Wikimedia Commons)