It was a vintage year for thoroughbred racing in America, and it took only two horses and one race to make it that way. In Seabiscuit and War Admiral the turf world in 1938 had two of the finest competitors in racing history. There were no other serious contenders for Horse of the Year honors, and each of the owners, Sam Riddle for War Admiral and Charles S. Howard for Seabiscuit, was certain his mount had a lock on the honor. The racing public was not so sure, and the best way to settle the issue seemed to be a match race.
Getting the two horses together on the same track proved rather complicated, however. Neither Riddle nor Howard was prepared to relinquish the slightest advantage—in scheduling, track condition or distance—to the other. And so the negotiations proceeded fitfully.
Seabiscuit, after winning the Bay Meadows Handicap in April, carrying the highest weight of his career, 133 pounds, shipped to New York's Belmont Park for the first proposed match with War Admiral. Everything seemed set when the Biscuit's trainer, Silent Tom Smith, declared him out. To race writers who wanted to know why, Smith explained in five words: "My horse lost his edge."
Having presumably regained it, Sea-biscuit was now sent to Boston to oppose War Admiral in the Massachusetts Handicap but was scratched when the track came up mud. ( Howard may have missed a bet here; War Admiral ran fourth that day.) Moving on to Chicago, the Biscuit entered the Stars and Stripes Handicap on July 4, but—giving away 23 pounds to War Minstrel—lost by 3� lengths.
Returning to the West Coast, Seabiscuit won the first running of the Hollywood Gold Cup at the new Hollywood Park track, a match race at Del Mar against Argentine-bred Ligaroti, and then headed East again. In the 1�-mile Manhattan Handicap he finished third to Isolater and Regal Lily, giving away 20 pounds, then won the Havre de Grace Handicap on Sept. 28 and ran second in the Laurel Stakes on Oct. 15.
While Seabiscuit was on his version of the Grand Tour, War Admiral had remained idle for three months after winning The Widener at Hialeah Park in March. He captured the Queens County Handicap on June 6 and shipped to Suffolk Downs for the aborted meeting with Seabiscuit in the Massachusetts Handicap. His fourth-place finish there stunned the big bettors, who had come to regard him as virtually a sure thing for show money. War Admiral recouped some of his credibility by winning the one-mile Wilson Stakes at Saratoga by eight lengths over Fighting Fox and erased doubts about his staying power by taking the 1�-mile Saratoga Handicap on July 30, the 1�-mile Whitney Stakes on Aug. 20, the 1�-mile Saratoga Cup on Aug. 27 and finally the two-mile Jockey Club Gold Cup at Belmont Oct. 1. The flashy 1937 Triple Crown winner never looked readier.
Meanwhile, working behind the scenes, Alfred Gwynne Vanderbilt, then the vice-president of Pimlico, got both sides to agree to a mile-and-[3/16]ths match race at the track on Nov. 1. A modest purse of $15,000-added was on the line, winner take all. The agreement stipulated that the track must be fast. Each owner posted a $5,000 forfeit bond to guarantee the appearance of each horse.
As the date for the race neared, veteran handicappers were taking a singularly optimistic view of War Admiral's chances. Indeed, many of them announced that the event would prove little more than a breezing workout for the Admiral. On the morning of the race two officials walked around the Pimlico layout and pronounced it officially fast. Word went out quickly, and by mid-afternoon 40,000 fans had arrived.
The two contending camps were preoccupied in the days before the race with questions of strategy. Seabiscuit's trainer, Smith, and Jockey George Woolf based their plans on a well-known fact about War Admiral. The fiery son of Man o' War never liked to be headed, and if possible would hold the lead at every post. The tactic allowed his rider to ease him up for a breather at some point during each race—usually midway in the backstretch—and left him with a strong finishing kick in the stretch. No jockey had ever risked battling the Admiral for the lead. Woolf would try.
There was one factor in Seabiscuit's favor. War Admiral was coming off races at longer distances, while Seabiscuit was moving up from a race at one mile. In the early going, at least, this could prove to be a significant plus.