Racecourse’s Pimlico Special on November 3, and Pimlico’s Riggs Handicap on November 5. Both horses were entered in all three. A meeting now seemed certain.

For Smith, the trip to Maryland was gratifying. His accomplishments with Seabiscuit were the wonder of the racing world, and the man who had been considered an obscure oddball a year before now enjoyed cult status among his peers. Across the backstretch, other trainers began to mix up homemade liniments, trying to brew what they called Smith’s “magic salves.” Everyone wanted to know what sort of shoes he was putting on his horses. They began to watch everything he did and query him about his training practices, from feed to workouts.11 One enterprising promoter even offered to pay Smith to hold training tutorials.

Smith was incredulous. He insisted that the training community was missing the point. It wasn’t the shoes or the liniments. “We have a great horse,” he said. “That’s all there is to it. And we tried to use common sense in training him and in racing him.”

There was one admirer whom Smith didn’t brush off. On October 16 he led a blanketed Seabiscuit into the paddock for the Laurel Handicap. Twenty thousand people crammed into the track to see him. As Smith walked Seabiscuit into the paddock stall, a stooped man emerged from the crowd and approached him.

“I’m Fitzsimmons,” he said, as if Smith didn’t know. “I want to ask you a favor.”

Smith, a little starstruck, listened.

“Mr. Smith, I am very fond of Seabiscuit, and I would consider it an honor if you would permit me to hold him while he is being saddled.”

Smith’s eyes shone as he handed Fitzsimmons the reins. He quietly saddled Seabiscuit while Fitzsimmons stood at the head of the horse he had lost. In a few moments the horse was ready, and Fitzsimmons passed the reins back and stepped away.12 Smith turned back to his horse and collected himself. It was, he would say later, the greatest moment of his life.

Ten minutes later Seabiscuit finished in a dead heat for first with a horse named Heelfly, who carried fifteen fewer pounds. In the jockeys’ room, Pollard surely never heard the end of it: George Woolf had ridden Heelfly.

The meeting with War Admiral, slated for the Washington Handicap, was just two weeks away.

A storm front rolled in and stalled over Maryland, drenching the track day after day. Smith urged Howard to pass on the entry in the Washington Handicap. Howard, ever the optimist, insisted that the track would be dry, and entered the horse. He was wrong. The morning of the race, an inspection of the track revealed a boggy surface, especially along the rail, where Seabiscuit preferred to run. This time they would not be pressured into starting. Seabiscuit was scratched. With Smith watching from the track apron, War Admiral led from wire to wire, winning easily.

After the race, Howard learned that members of the Riddle barn were publicly mocking him for being afraid of War Admiral.13 He was furious. Though both horses were still entered in the Pimlico Special and Riggs Handicaps, each race would feature a full field. Howard and Smith much preferred that the horses meet in a definitive one-on-one match, in which no other horses could cause interference or otherwise affect the outcome. Howard again tried to arrange a match race.

The man he approached was Alfred Gwynne Vanderbilt, Jr. A dead ringer for actor Jimmy Stewart, Vanderbilt was a gangly twenty-five-year-old whose gentle, self-effacing manner belied his fabulous wealth.14 His father was heir to the Vanderbilt railroad and oceanic shipping fortune; his mother’s father had invented the fantastically lucrative Bromo-Seltzer. In May 1915, when a German submarine torpedoed the Lusitania and sent the liner and Alfred’s father to the bottom of the Atlantic, two-year-old Alfred had inherited $5.8 million in government bonds, a fortune augmented by $2 million more and a sprawling Maryland property when he turned twenty-one in 1933. Dubbed the nation’s most eligible bachelor, Vanderbilt eschewed the debauchery that would have tempted other men fresh out of their teens and into a bottomless bank account. He had fallen madly and intractably in love with horse racing from the moment he saw his first race as a child, and knew where he wanted his money to go. He bought controlling interest in Baltimore’s legendary but struggling Pimlico Racecourse and set out to restore its glory. In spite of his youth, he proved to be an imaginative and effective businessman. He revolutionized Pimlico, installing a public-address system and a modern starting gate and leveling out the large hill in the infield that had given the track its nickname—“Old Hilltop”—but obstructed the view of the races. By the fall of 1937 Pimlico was beginning to make a comeback, but progress was slow. Vanderbilt wanted a headliner.

Howard recognized Vanderbilt’s tremendous influence and powers of persuasion, and knew that Pimlico needed his horse. He proposed that Vanderbilt try to host a meeting between Seabiscuit and War Admiral. He told him that he’d take a match at any distance from a mile to a mile and a quarter, anytime the track was fast. He offered to run against the colt for a small purse or simply for a winner’s cup. “I believe Seabiscuit can beat War Admiral,” he said.15 “Maybe I’m wrong, but I’m willing to run against him to test the theory. It is all up to Mr. Riddle.” Vanderbilt approached the elder horseman with an offer for a match race for $50,000. Riddle declined.

Howard was left with either the Pimlico Special or the Riggs. At first, it appeared that both horses would run in the former, and Maryland geared up for the meeting of the two titans. Again, the weather intervened. Ten straight days of downpour kept Seabiscuit in the barn, taking the edge off of his form. Smith again scratched him.

On race day, Smith walked out to the track to see War Admiral run. The Triple Crown winner was a hellion, repeatedly barging through the gate and dragging the assistant starter with him. War Admiral was growing so violent that he was endangering himself and everyone nearby. Head starter Jim Milton tried a new tack. He brought the colt around to the front of the gate, had the assistant place a pair of tongs on the horse’s lips to distract him, then had him backed into the stall.16 It worked. War Admiral quieted down and Milton was finally able to break the field in good order.

Across the track, Smith lifted his binoculars and watched as War Admiral pulled around the far turn, meeting with unexpected pressure from Masked General, who carried twenty-eight fewer pounds. Smith saw Masked General level his eye right at War Admiral. It lasted only a moment, but that was all Smith needed to notice something unusual. For the first time in his career, War Admiral hesitated. Smith thought: He is befuddled.17 War Admiral’s jockey, Charley Kurtsinger, also seemed confused. An instant later, War Admiral pulled himself together and won, regaining the lead in the money-winning race. But Smith took note. He believed he had found a way to beat War Admiral. After the race, he was smiling.

“Seabiscuit,” someone heard him saying, “will lick him sure.”18

Riddle was furious with Milton for using the tongs on War Admiral, despite the fact that one of his own employees had reportedly given them to Milton to be used on the colt if he acted up. Riddle had been harboring a grudge against Pimlico since 1926, when the track’s racing secretary had assigned his colt Crusader 126 pounds in a major race—Crusader lost to a horse carrying 93 pounds.19 The tongs incident was the last straw. Riddle didn’t want Milton going anywhere near his horse again, and vowed never to run another horse at Pimlico. He had Conway shelve War Admiral for the season.

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