Setting aside an ambition to be a Canadian Mountie, Woolf began race riding while in his mid-teens, apparently padding his age by a year. He cut his teeth on Montana match races, relays on unpedigreed horses in Indian country, and contests at rough tracks with names like Chinook and Stampede. Freddie Johnson and Russ McGirr were quick to snatch up Woolf’s contract and watched as their purchase became a smashing overnight success in the minor leagues. In 1927 Woolf was spotted by Lewis Theodore “Whitey” Whitehill, a top horseman, who soon called a meeting with Johnson. Whitey had a good claimer named Pickpocket that caught Johnson’s eye; Whitey was equally enamored of Woolf’s riding. An even swap of horse for boy was made. Whitey brought Woolf to Vancouver, then down to Tijuana, and turned him loose.
No one had ever seen anything like George Woolf. Right out of the box, he won every prize that wasn’t nailed down. He was something to watch, pouring over his horse’s back, belly flat to the withers, fingers threaded through the reins, face pressed into the mane, body curving along the ebb and flow of the animal’s body. He could learn a horse’s mind from the bob of the head, the tension in the reins, the coil of the hindquarters. Fifths of a second ticked off with precision in his head; Woolf timed his horses’ rallies so precisely that he regularly won races with heart-stopping, last-second dives. He could, racetrackers marveled, “hold an elephant an inch away from a peanut until time to feed.” He had an uncanny prescience, as if he lived twenty seconds ahead of himself, seeing the coming trap along the rail or the route to the outside. His commands had the understatement of the ancient cavalry art of dressage. He was shrewd and he was fearless, demonstrating such cold unflappability in the saddle that race caller Joe Hernandez gave him the nickname “Iceman.” It stuck.
Woolf’s phenomenal success came partly from God-given gifts, partly from experience, and partly from exhaustive study. He prowled the heads of his mounts and everyone else’s, scouring the Daily Racing Form for every tidbit of information that could give him an edge, and cracked contests wide open by ruthlessly exploiting his rivals’ weaknesses. His memory was a catalogue of vital notes on horses and men: hangs in the stretch, balks in close quarters, only hits right-handed. He also developed a race-preparation technique that was a half century ahead of its time. Sitting in the jockeys’ room before a race, he would close his eyes and visualize how the race would be run. He would see the pitfalls and opportunities develop and run the race in his head until he saw how to win it. He didn’t ride his races, said his archrival Eddie Arcaro, he crafted them.
Like all athletic greats, Woolf was a driving perfectionist. He abruptly sold his tack and announced his retirement in disgust over a ride he thought was poor. After being briefly suspended for making a mistake in a race at Tijuana in 1930, he stomped up to the jockeys’ room, cleaned out his locker, lugged everything outside, heaped it into a big pile, and set the whole mass on fire. “Me, ride again?” he said. “No siree.” He then jumped into his convertible, sped all the way to Canada, stopped at the first Mountie station he found and tried to enlist. Rejected for his diminutive stature, he sequestered himself in the Canadian wilderness, “a-huntin’ and a-fishin’.” Months later he reappeared in the jockeys’ room and went back to riding the hide off of every jockey in town.
As Woolf matured and honed his craft, his moments of self-loathing gave way to quiet, unwavering confidence. He was greatness fully realized, and he knew it. Where other elite athletes betray their doubts about their capacities with displays of touchy egotism, Woolf was utterly insouciant. He could not be rattled. “George,” remembered racing official Chick Lang, “was a guy that you could put on a street corner, and two cars would have a head-on collision right in front of him, and he would say, ‘Gee, look at that,’ while everybody else would be running in all directions.” He seemed devoid of fear. On the track, while other riders flailed and winced and scratched their way around, the Iceman “sat chilly,” as loose as water, his legs and hands supple and still. Photographers shooting races would record jockeys in various attitudes of strain; in the middle of it all would be Woolf, smiling the way a man does when he humors a child. While other riders dragged themselves to the barn to gallop horses at 4:00 A.M. seven days a week, compelled by a biting fear that their skills would wane or trainers would forget them, Woolf slept in, rarely showing up at the track before noon. “He was a better rider than most of us, and he knew it,” remembered fellow jockey Mosbacher. “So he just kind of took the easier way.”
Woolf was an uncensored man, in word and deed. “As a jockey,” wrote Red Pollard’s friend David Alexander, a columnist for the Morning Telegraph, “Woolf is noted for doing exactly the right thing at exactly the right time. He is also noted for saying what some persons consider the wrong thing at the wrong time.” When asked a direct question, he could be counted on to say something so bald—and undeniable—that he would leave everyone around him gaping. After losing one major race on a highly regarded runner, he flatly told the national press, surely to the horror of the owner, that the horse just wasn’t any good. On the night after Woolf won a top stakes race, the owner of the winning horse called to invite him to a postrace soirée with the moneyed set. “You tell ’em,” Woolf replied, kicking back with a big steak, a long, cool beer, and a group of his roughneck friends, “that if the horse had got beat, they wouldn’t invite us over. We got a party of our own.”
“Woolf,” remembered his close friend Bill Buck, “done what Woolf wanted to do.” Throughout his career, if he felt like taking a day off, he’d just pack up and go, leaving his exasperated agent and jilted trainers hunting for him. On one occasion, after he failed to appear for several potentially lucrative races, his agent found him starring in a bull-riding exhibition. He once vanished without a trace a few days before the Preakness Stakes, throwing the entire Maryland racing community, including an owner who wanted him to ride one of the race favorites, into an uproar. He glided back to civilization three days later, tanned and happy. While driving through Pennsylvania he had simply happened upon a beautiful lake, pulled over, and taken an impromptu fishing vacation in perfect serenity. When he disappeared on another afternoon, horsemen eventually found him in a crowd watching a visiting Montana rodeo. A trick rider had claimed that he could jump a car while riding two horses simultaneously, “Roman” style—a foot in one stirrup of each. Woolf called his bluff and volunteered his gleaming new Cord roadster for the job. The horses nicked the car up pretty good but made it over. Woolf felt the spectacle was worth the price of new paint and a furious agent.
Only his contract trainer, Whitey, was unfazed by his jockey’s behavior. This needled Woolf. To raise Whitey’s blood pressure a bit, Woolf started delaying his horses’ rallies until the last possible second. He would send a friend to sit nearby and watch the color drain from Whitey’s face as Woolf waited, and waited, and waited before driving for the lead just when it seemed too late. Whitey surely whitened a little more with every closing kick, but the Iceman knew what he was doing. Incredibly, Woolf’s timing was so good that he rode for more than a decade