By September 1920, Man o’ War had no competition left. He had faced all of the best three-year-olds in races like the Preakness, the Dwyer, and the Travers Stakes, and beaten them all. In the process, he had demonstrated overwhelming superiority, winning by many lengths and setting records nearly every time he went to the barrier. Of course, he had not run against older horses — yet.
What if? Fans asked. What could he do against his elders? Speculation abounded about which of the older horses racing could possibly be Man o’ War’s better.
A year after his storied string of wins, Sir Barton seemed to be back in rare form. He had set a track record in the Saratoga Handicap and followed it up with two more victories, including a thrilling stretch battle with Gnome in the Merchants and Citizens Handicap. Now the owner of speed records of his own, Sir Barton stood out as the best challenger for the big red colt. Each had been called the “horse of the century,” compared to Colin and Sysonby, and competed at unprecedented levels of stamina and speed.
Man o’ War v. Sir Barton? Fans salivated at the thought. Their trainers and owners had to warm up to the prospect.
Man o’ War had only one chance to win all of these prestigious three-year-old stakes and, with luck, would race at four, giving him plenty of time to face horses like Exterminator and Sir Barton. Racing against older horses might expose the colt’s fallibility and his owner, Samuel Riddle, was not ready to do that. On the other hand, he wanted to break Domino’s career record of $193,550 and this match race could mean big money.
Commander Ross, Sir Barton’s owner, thought of himself as a great sportsman and did not shy away from the thought of racing his Triple Crown winner against the ascendant Man o’ War. Being a good sport did not mean he was a fool, though: Ross knew what his horse was up against. He had seen Man o’ War race multiple times. Sir Barton had proven to be a great champion, but Riddle’s colt had redefined that term each time he met the barrier. Yet Ross could not resist the lure of pitting the best horse he would ever own against the best horse the sport had ever seen.
With that, Ross and Riddle agreed to hold out for an offer of at least $50,000 for a match race. In mid-August, the inimitable Colonel Matt Winn had offered them $25,000 plus a gold cup to meet in Kentucky; Laurel Park had offered $30,000. The longer the two owners held out, the higher the offers went. Finally, a promoter from Ontario, Abe Orpen, threw down the gauntlet: $75,000 plus a $5,000 gold cup, winner-take-all. Trying to bring the match race to his Kenilworth Park, Orpen was determined to beat Matt Winn and have the two owners sign on the dotted line before the Colonel could return with an even more lucrative offer. On September 24, 1920, Commander Ross and Samuel Riddle finalized the agreement with Orpen: Man o’ War and Sir Barton would meet at Kenilworth Park on October 12 for a 1 1/4 miles match race with a $75,000 purse and a $5,000 gold cup. Their agreement capped off a frenzied set of negotiations that involved jockeys, weight, and a third party that wanted more than Orpen, Ross, and Riddle were willing to give.
Initially, the proposal had involved three horses, not two: Man o’ War, Sir Barton, and the great distance racer Exterminator. Willis Sharpe Kilmer, Exterminator’s owner, had wanted the match race to be 1 1/2 miles, that extra distance giving his gelding more of a chance against the speed of both Man o’ War and Sir Barton. He’d also wanted handicap conditions, with Walter Vosburgh assigning the weights. Neither Riddle nor Ross wanted any part of that; Riddle feared the weight that Man o’ War might carry, especially after carrying 138 pounds in the Potomac Handicap. Commander Ross knew that Sir Barton would carry similar weight, especially after his August victories. When it was clear that Kilmer was out of luck, he bowed out from the negotiations, leaving racing fans to wonder always how Exterminator would have fared against the big red colt.
Finally, after questions about who Clarence Kummer would ride for (Riddle) and how much weight each horse would carry (120 pounds for Man o’ War and 126 pounds for Sir Barton), the match race was on. Man o’ War v. Sir Barton. Their meeting would be Man o’ War’s only race against an older horse and the last race of his career. For Sir Barton, this was a chance to emphatically prove his dominance and show the talent that had made him America’s first Triple Crown winner one more time. One more chance to shine as brightly as the big red colt that challenged him.
You can read more about the negotiations that led to the match race between Man o’ War and Sir Barton in Sir Barton and the Making of the Triple Crown (coming May 2019 from the University Press of Kentucky) and Dorothy Ours’s Man o’ War: A Legend Like Lightning.