This book is a history that centers around a very unique horse, Seabiscuit, who was sired by the speedy but temperamental Hard Tack on a mare named Swing On. The author also depicts three other men who are key to Seabiscuit's story: his owner Charles Howard, his trainer Tom Smith, and his two jockeys John "Red" Pollard and George Woolf.
Structurally, the book proceeds in chronological order, but breaks away to provide such back-story as is necessary to put Howard, Smith, Pollard, and Woolf's decisions in an appropriate context.
Chapter 1 describes Charles Howard's early life, his rags-to-riches career as a bicycle salesman turned automobile dealer and then distributor. It also describes the accidental death of his son, Frankie, in a car accident, the collapse of his first marriage, and the introduction of horse racing to Tijuana in conjunction with the economic effects of Prohibition. It also describes the circumstances under which Howard met and married his second wife, Marcela, and the unusual chain of events that made Howard get involved in horse racing.
Chapter 2 discusses the background of Tom Smith, who was a man of few words but a brilliant trainer of horses. He begins working for a barn owner by the name of Irwin, and unlike many of his peers whose strategies were based chiefly on superstition, Smith learns to approach each horse as an individual and to tailor his training approach.
Chapter 3 describes Seabiscuit's lineage and early life. The foal of a mare named Swing On by the fast infamously vicious stallion Hard Tack, who was in turn sired by the legendary Triple Crown winner Man o' War (who also sired War Admiral). Seabiscuit was small enough to be mistaken for a pony, shaggy, and awkward-looking. He was also intelligent, lazy, and being brought up in a stable where trainers had no time for him. The chapter ends with his discovery by Tom Smith, who arranges for Howard to buy Seabiscuit.
Chapter 4 introduces John "Red" Pollard and George "Iceman" Woolf, two jockeys who were friends throughout their career but eventually parted ways over Seabiscuit. Both riders were from the Canadian province of Alberta. Pollard came from Edmonton, and George was from the Cardston area farther south.
Chapter 5 provides background information on the life of a jockey in the first half of the 20th century. It describes the weight limits, the fasting and sweating athletes endure to make weight, and the physical dangers and injuries that occur.
Chapter 6 describes the conditions in Tijuana, particularly the hilltop Molino Rojo ("red mill" in English, "moulin rouge" in French, and yes, it's an almost universal phrase for a brothel). Both Pollard and Woolf avoided that particular establishment: Woolf married a waitress named Genevieve in 1931, as his career was taking off. Red Pollard's had stalled.
Chapter 7 describes Tom Smith's approach to training Seabiscuit. Instead of pressuring him, he let the horse do what he wanted, so that instead of fighting against his jockey or handler he would direct his competitive energy to the racetrack against other horses. After a few weeks of this, Seabiscuit starts to show speed and courag. In the fiftieth race of his life, Seabiscuit finally starts to understand the game.
Chapter 8 describes Seabiscuit's early successes in handicap races. The horse finally starts to show his speed and is particularly good at holding his speed while turning tightly. Seabiscuit starts to break track records and win races without even trying. But in his first try at the Santa Anita, Seabiscuit is defeated by a horse named Rosemont in a photo finish.
Chapter 9 is set in 1937, when the United States is still in the grip of the Great Depression. The introduction of radio made live broadcasts viable coast to coast, and the technology brought the nation together. The nation was in desperate need of a hero, and found one in Seabiscuit, who became a celebrity. The ugly horse from the Cinderella background, who came out of nowhere and nearly won the Santa Anita, captured the public imagination. But this created difficulties for Tom Smith, who did not appreciate the attention or the distraction. False rumors of injuries started to circulate, and that just increased the media attention. The chapter describes some of the ruses Smith used to distract reporters by switching Seabiscuit with his slower but identical-looking brother Grog.
Chapter 10 begins with some background materia introducing War Admiral, a Triple-Crown winner, the near-black colt was physically beautiful and devastatingly fast. After establishing this horse as Seabiscuit's eventual target, the chapter reverts to a description of how Seabiscuit and a filly named Fair Knightess went head to head at the Massachusetts Handicap, with Seabiscuit finishing ahead. The filly became Seabiscuit's training partner when the Howards bought her. But the biggest challenge introduced in this chapter is the way the impost or handicap weight for Seabiscuit was rising to the point where it was creating a risk of injury to the horse. It also introduces one of Seabiscuit's weaknesses as a racer: his difficulties running in mud or on a wet track. Seabiscuit does not win all his races: he runs in the mud at Narragansett and finishes fourth. But he wins the Continental Handicap in New York, winning more in 1937 than War Admiral. But Howard and Smith scratch Seabiscuit from every race in which the track is boggy or wet, or if Seabiscuit shows the slightest sign of fatigue or strain. Meanwhile the rivalry between Charles Howard and his son Lin is introduced.
In Chapter 11, Red Pollard is briefly suspended when the horse he is riding suddenly spooks and changes course during a race. Howard intervenes on Pollard's behalf, but the track stewards extend Pollard's suspension not just from his weekday mounts but to all horses. At this point, Pollard approaches Howard and suggests that he get George Woolf to ride Seabiscuit. Howard does not agree. Seabiscuit begins to receive very high imposts, and Howard keeps scratching him out of every race in which the impost is abouve 130 pounds. Meanwhile, a man is caught attempting to sneak into Seabiscuit's stall and shove a sponge up his nose to interfere with his breathing. Worst of all, Pollard is injured riding Fair Knightess. At this point, Howard agrees to let a jockey named Workman ride Seabiscuit. Seabiscuit finishes second in the San Antonio, and Woolf is poised to ride Seabiscuit in Santa Anita.
In Chapter 12, the week prior to the 1938 Santa Anita Championships goes poorly. Seabiscuit gets a cough, there is a plot to kidnap Woolf, and during the race Seabiscuit is fouled by a horse named Count Atlas not once or twice but repeatedly. Woolf uses his whip on Count Atlas's jockey to make him back off. But after the drama is done Seabiscuit is far back in the race. Woolf gallops Seabiscuit forward, is overtaken by the lightly-weighted Stagehand, but Seabiscuit accelerates again for another photo finish... and another loss.
In Chapter 13, Woolf is suspended for his use of the whip on another jockey, and Howard sets up a race between Seabiscuit and War Admiral at Belmont.
In Chapter 14, Tom Smith resorts to unusual strategies to change Seabiscuit's natural running style and make him break early to avoid giving War Admiral too much of a lead. The ongoing cat-and-mouse game between Smith and the press continues, but Seabiscuit's speed is gone. His knees are slightly sore, so they scratch him from the race. War Admiral is scratched almost immediately after that at a stakes race.
In Chapter 15, Red Pollard is seriously injured. His right leg is seriously broken and is almost completely severed below his knee. The doctors are able to save his leg but he may never race again. In Boston, Seabiscuit strains a tendon running up the back of his left foreleg and cannot run, but when Tom Smith announces it he is not believed due to Seabiscuit's history of scratches and Smith's practical jokes on the press. The race goes on withou him but War Admiral cuts his hoof.
In Chapter 16, Seabiscuit places second in a race in Arlington and wins a $50,000 purse in Hollywood Park, having recovered from the tendon injury.
In Chapter 17, the rivalry between Lin Howard and his father comes to a head in a match race between Seabiscuit and Lin Howard's horse Ligaroti. Seabiscuit wins, but Ligaroti's jockey Spec Richardson fouls Woolf repeatedly and starts what amounts to a brawl on horseback. There is an inquiry almost immediately, and both jockeys are suspended from all California tracks, but a film of the race shows that Woolf acted in self defense, so the press lobbies to have the suspensions lifted.
In Chapter 18, Red Pollard turns twenty-nine years old but could have passed for sixty. He falls in love with his nurse, Agnes, who agrees to marry him. Alfred Vanderbilt, who has just married Marcela's niece, sets up a match race between Seabiscuit and War Admiral at the Pimlico racetrack. Although the track is wet, George Woolf finds a firmer stretch where the tractor wheels were.
In Chapter 19, Charles Woolf races Seabiscuit against War Admiral and wins handily.
In Chapter 20, Pollard is up and walking but breaks his leg a second time by tripping while out walking. Seabiscuit is being trained for the Santa Anita starting in the fall. He is drawing more newspaper coverage than President Roosevelt or Adolf Hitler, and is being assigned high imposts, 134 pounds for 1939. But in a prep race, Woolf feels Seabiscuit stumble. At first the horse seems uninjured, and he rallies to finish second, but he has ruptured his suspensory ligament in his left front ankle. Another Howard horse named Kayak II wins the Santa Anita.
In Chapter 21, Red Pollard marries Agnes and Seabiscuit starts walking about and running again. He manages Seabiscuit's rehabilitation along with his own.
In Chapter 22, Seabiscuit returns to racing. It is now 1940. Pollard wants to ride Seabiscuit, but Woolf is tapped as the backup jockey. An argument over Seabiscuit ends the jockeys' long friendship.
In Chapter 23, Seabiscuit finally wins the Santa Anita, with Pollard riding him.
The Epilogue briefly finishes off the life stories of Seabiscuit, Pollard, Howard, and Smith.