The summer of 1920 had reluctantly yielded to autumn, yet despite the wishes of horse racing fans, there had been no meeting between the king of the 3-year-olds, Man o' War—who had laid waste to his peers as he strode through 10 starts undefeated and, quite frankly, untested—and a worthy older group of horses that included Triple Crown winner Sir Barton and the grand handicapper Exterminator.
Although American tracks had attempted to lure such a showdown by offering some big-money incentives to regular stakes on the racing calendar, none had come to fruition.
North of the border, the enterprising chairman of Canada's Kenilworth Jockey Club, A.P. Orpen, proposed an event at the recently established track in Windsor, Ontario, with the following conditions: a $50,000 weight for age race (126 for Sir Barton, 120 for Man o' War) over 10 furlongs, Tuesday, Oct. 12, rain or shine, all dependent on the well-being of the horses involved.
Exterminator's owner, W.S. Kilmer, opted out as he did not like the 10 furlongs, preferring a race of 12 furlongs or two miles, which would better suit his distance-loving gelding.
As great minds run in the same vein, Matt Winn of the Kentucky Jockey Club was working on a similarly conditioned race to lure the combatants to either Churchill Downs or Latonia.
Getting the jump on Winn, Orpen upped the ante to $75,000, winner take all, and a $5,000 gold cup, and traveled to Havre de Grace in Maryland to meet with Sam Riddle, Man o' War's owner, and fellow Canadian Commander J.K.L. Ross, who owned Sir Barton.
As the deal was being confirmed in Maryland, Winn's last-minute counteroffer (perhaps as much as $100,000) came a bit too late.
Chestnuts of different hues, Man o' War and Sir Barton were kind of like cartoonist Bud Fisher's Mutt and Jeff of the racing world: Man o' War, the tall and lanky Mutt; Sir Barton, the short, compact Jeff.
Louis Feustel was conditioning Man o' War at Belmont Park in New York while H.G. Bedwell had Sir Barton at Laurel Park in Maryland.
Both horses came to Canada in the finest of fettle, Sir Barton riding a four-race win streak that included the Dominion Handicap at Canada's Fort Erie racetrack.
A third horse, G.J. Long's Wickford, was entered for the $75,000 ($1,019,738 today). Truly the odd horse out, Wickford had won a single race and was 0-for-15 on the year, yet his entry was essential. The rules of the Canadian Racing Association did not allow match races; therefore, Wickford was duly scratched.
Earl Sande, the regular rider of Sir Barton, was also a scratch. Ross, unhappy with Sande's "not in good form" performances, replaced him with Frank Keogh. Regular rider Clarence Kummer was aboard Man o' War.
The race of the ages drew more than 25,000 fans (at $5 a head) to Kenilworth, most just for the Kenilworth Park Gold Cup. As was his wont, Man o' War made a headlong plunge for the lead as soon as the barrier sprung upward. Using the metronomic rhythm of his lengthy strides, Man o' War ticked off the quarters almost evenly as he gained momentum under restraint. From two to five lengths ahead with four furlongs to run, the big red bullet was seven to the good at the wire in 2:03, a track record.
To the victor go the spoils: A lasting image of the race shows Man o' War drinking water from the gold cup in the winner's circle.
The 20th victory in 21 starts, this was Man o' War's last hurrah.
