As the only horse to ever defeat the vaunted Man O' War, Upset’s legacy has become one of the most oft told stories in thoroughbred racing. Off the track, however, the average sports fan has little knowledge of the immeasurable impact Upset would have on the entire sporting world.

On August 13, 1919, Payne Whitney Stable’s Upset lined up against the top thoroughbreds at Saratoga’s Sanford Memorial. A relatively short race at 6 furlongs, Upset had his work cut out for him facing the highly regarded Golden Broom (who had recently won the Saratoga Special on the same track) and, of course, the heavily favored Man O’ War. Having already lost to Man O’ War at the U.S. Hotel Stakes, Upset was not considered much of a threat. In spite of the odds, Upset would have two advantages at post time. Man O’ War and Golden Broom would each have to carry 15 pounds more weight than Upset and Saratoga’s regular starter would miss the race leaving the starting flag in the hands of a less experienced substitute starter. The result was the most talked about controversy of the era.

The Sanford Memorial was held before the advent of starting gates. The horses would enter the raceway as a group and line up along the starting line. Before jockey Johnny Loftus could get Man O’ War lined up properly, the substitute starter dropped the flag and the horses were off. Man O’ War was caught with his back to the rest of the field.

Midway through the race, Upset was riding third behind Golden Broom and Donnacona. Approaching the home stretch, Golden Broom slowed under the 130 pounds of added weight, allowing Upset to creep towards the lead. Man O’ War, having righted himself, quickly caught the slower horses in the pack. After passing Captain Alcock, The Swimmer, and Armistace, Man O’ War steered towards the rail in an attempt to catch the leaders. Donnacona also began to fade moving towards the rail and relinquishing the lead to Upset. Blocked by the slowing Donnacona, Loftus was forced to steer “Big Red” back towards the center of the track. Man O’ War lost valuable time and soon ran out of track. Upset was the victor by the smallest of margins… a half a length. Upset’s jockey Willie Knapp describes the end of the race:

"We'd passed the quarter pole and were going to the eighth pole, I guess it was, and I heard something right behind me and I knew it was Big Red coming at me now. I looked back and there he was. Johnny Loftus was riding like a crazy man and he yelled at me, `Move out, Willie! I'm coming through!' So I yelled back at him, `Take off! Take off me, bum, or I'll put you through the rail!' Then I set down to riding and we won."1

Upset ran the race of his life, completing the 6 furlongs in 1:11 1/5.

Man O’ War would go on to be one of the most successful horses in racing history. He won 20 of 21 races in 1919 and 1920 (including a rematch with Upset at the Grand Hotel Stakes), setting three world records and being staked at an unheard of 1-100 three times. (For the uninitiated, that means you would have to bet 100 dollars just to win 1).

In the end, however, Upset has become the most mentioned athlete in sports. Whenever the underdog emerges victorious, we subtely refer to the 1919 Sanford Memorial, when Man O' War suffered his only loss. A dramatic "upset" at the hands of Upset.

1http://www.fortunecity.com/marina/commodity/1881/manowar.html