On October 12, 1920, about 3.37 pm, two horses stood at the barrier on Kenilworth Park’s dirt oval. The largest crowd ever to grace the stands watched as the two took to the track, one clad in Ross orange and black and the other in the yellow and black of Samuel Riddle, each known as the best of his class. As they lined up by the starter, one towering over the other, their riders took their positions, gripping the leather reins and waiting for this particular job to begin.

The match race itself had come together rather quickly, a response to the drumbeat of desire that threatened to drown out everything else in thoroughbred racing that fall. Man O’War had conquered all comers to that point, save for a slight blip on the map named Upset, but his owner’s caution had left one question still to be answered: how would Big Red fare amongst older horses? When Willis Sharpe Kilmer dropped his Exterminator out of the mix, Sir Barton became the symbol of the best that the older class had to offer: record setter under heavy weights, Triple Crown winner, the star of the Ross Stable. For the champion, though, the one who had done what Man O’War hadn’t, 1920 had been a hard campaign, with eight starts, three in August alone, after thirteen in 1919. Sure, Man O’War had had ten starts in 1920, but he didn’t have the shelly hooves that plagued Sir Barton. The track at Kenilworth was hard and fast, thanks to Abe Orpen’s hope for a speed duel. For Sir Barton, the solid surface and the residual soreness of a long campaign brought on lingering questions about soundness, but no one in the Ross camp was going to give their hand away. Kenilworth, though, had taken on a dour air as a result. As J.K.M. Ross laments in Boots and Saddles, this was “a battleground for greatness and a breeding ground for disappointment and distortion” (207).

With his obvious advantages in height and muscle, it was clear how tremendous Man O’War was next to Sir Barton. While the Triple Crown winner was not the largest horse, he clearly showed why he had been so good on the track versus so many of the era’s best horses. Standing there at the barrier, though, Sir Barton looked like a common plater next to Man O’War. The race was nearly a foregone conclusion, but Ross’s sense of sportsmanship wouldn’t allow him to withdraw from the contest. In the end, Man O’War’s conquering of his competition only intensified the ascendency of his star. For Sir Barton, though, it might have been the contributing factor to his slow fade into near obscurity.

Ninety-six years ago today, the Kenilworth Gold Cup was the match race that turned out to be no match at all. For Man O’War, the race resulted drinking champagne from the race’s gold trophy and retiring to stud to make an indelible and lasting mark on the pedigree of all thoroughbreds racing today. For Sir Barton, it was the end. He ran two more times, but his soundness and heart weren’t up to the task. He went quietly to stud and then, because of death and circumstance, to the Wild West, resting for all time in rural Wyoming.

But he left his mark loudly even if he went off quietly into the night. It’s in the walls of noise at Churchill Downs and Pimlico and Belmont in the spring. It’s in the vaunted places of horses like Citation, Secretariat, Affirmed, and now American Pharoah in the pantheon of thoroughbred racing. He may not have been a behemoth on the track, but his achievement on those spring days in 1919 has become the yardstick by which we measure all horses to this day.

Not even Big Red wears his crown.