Man o' War all-time greats with an "almost unbelievably brilliant performance" before a crowd of 25,000. At odds of 1-20, he faced only one rival, the well-regarded colt Donnaconna. Man o' War led from the start and Kummer let him run freely at the top of the stretch, allowing Man o' War to draw away by 20 lengths. Although eased in the final furlong, Man o' War set a world record of 2:14, beating the previous standard set in England by over two seconds and beating Sir Barton's American record by over three seconds. This time stood as the American record until 1961
Man o' War organizers tried to lure Sir Barton into entering by promising to increase the purse from $15,000 to $25,000 if he did so, but Sir Barton needed more time to recover from his last race. It was also speculated that Sir Barton's owner was holding out for an even higher purse for a match race with Man o' War. The connections of Exterminator, another future Hall of Famer, were also considering the race but ultimately bypassed it because under the weight-for-age conditions of the Gold Cup, he would have had to concede Man o' War five pounds. As it was, Man