It was a rough place to start a career. Racing in the bush leagues was utterly lawless.9 “If you could survive there,” remembered former jockey Joe “Mossy” Mosbacher, “you could ride anywhere.” With no race cameras and only two patrol judges to oversee them, jockeys could—and would—do anything to win. Jockeys on trailing horses grabbed hold of leading horses’ tails or saddlecloths so their own horses could be towed around the track, saving energy. They joined arms with other jockeys to “clothesline” riders trying to cut between horses, formed obstructive “flying wedges” to block closers, and bashed passing horses into the inside rail. They hooked their legs over other jockeys’ knees, ensuring that if their rivals moved forward, they’d be scraped off their saddles. They dangled their feet in front of passing horses to intimidate them, and when less inspired, they shoved and punched one another and grabbed one another’s reins. Because many of the tracks had no inner rail, some jockeys simply cut through the infield, dodging haystacks, to win. In some cases, riders toppled their opponents right off their horses.
Such tactics were, until the mid-1930s, seen at all levels of racing, but nowhere were they used with such ruthlessness as on the bush tracks where Pollard got his start. According to the great jockey Eddie Arcaro, who once rammed another rider over the rail in retribution for a bump (“I was trying to kill that Cuban S.O.B.,” he told the stewards, who reformed him with a year’s suspension), the desire to win wasn’t the only motivation.10 The bush leagues contained two kinds of riders: kids like Pollard seeking to make their names and veterans in the bitter waning days of their careers, sliding down to this last and lowest place in the sport. “To succeed in those days, you had to fight for everything you got,” Arcaro wrote in his autobiography, I Ride to Win!11 “You were competing with men who were aware that their own particular suns were fading, and they resented your moving into the places they would leave. They fought you, and you fought them back.”
Pollard took a few licks, held his own, and learned a lot. But months passed, and still he didn’t win a single race. In danger of starving, he used the only other skill he had, straying into carnival bullrings and cow-town clubs to moonlight as a prizefighter. He was no headliner. Mostly, he boxed in preliminary matches to warm up the crowd. At the time, a local kid nicknamed “the Nebraska Wildcat” was the hottest boxing property around.12 In imitation, Pollard took the ring name “Cougar.” His skills didn’t live up to the nickname. He fought a lot of matches, and lost, he said, “a lot of ’em.”
Though a misnomer, his nickname proved to be the one enduring thing about Pollard’s ring career. Racetrackers in that era had a peculiar animosity for given names. Among those haunting the track in Pollard’s day were Lying Tex, Truthful Tex, Scratchy Balls John, Cow Shit Red, Piss-Through-the-Screen Slim, and a man the trackers called Booger. Baptist John was the nickname of a tracker famed for being run over by a police car that was chasing him, breaking his leg.13 He left the cast on his leg until it rotted off, so that, in the words of horseman Wad Studley, “one leg went north and the other one southwest.” The given names of half the people at the track were complete mysteries. The name Cougar followed Pollard from the boxing ring to the races and stuck with him for good. He liked the name, referred to himself by it, preferred that his closest friends use it, and gave it to every dog he ever owned.
A year passed. Pollard didn’t win a race. The break he needed came from a genial old former jockey named Asa C. “Acey” Smith, a traveling “gyp,” or gypsy, trainer. Passing through Montana, Acey thought he saw promise in Pollard, signed him on as his rider, and brought him on a road trip to western Canada. It was at a little fair track that Pollard finally rode a winner, H. C. Basch, in a mile-and-a-half race in the fall of 1926. It was a momentous event. Once a rider logged his first win, he officially became an apprentice jockey, or “bug boy,” so called because of the asterisk, or “bug,” that was typed next to apprentices’ names in the racing program.14 Then as now, all racehorses were assigned a weight, called an impost, to carry in each race.15 The impost consisted of the jockey, his roughly four and a half pounds of saddle, boots, pants, and silks, and, if necessary, lead pads inserted into the saddle. To help aspiring riders establish themselves in the sport, a horse ridden by a bug boy had his impost reduced by five pounds. The bug offered a substantial break: The rule of thumb is that every two to three pounds slows a horse by a length in racing’s middle distances of a mile to a mile and a quarter, while in longer races every pound slows a horse by one length. Bug boys enjoyed the weight break until they rode their fortieth winner or reached the anniversary of their first win, whichever came first. After that, they were journeyman riders.
In that era virtually all jockeys were signed to stable contracts, which were clear and simple. In exchange for housing—usually a cot in a vacant horse stall—and about $5 a week for food, bug boys gave the trainer first call on their riding services, their toil in an unending stream of barn chores, and authoritarian control over their lives. Journeymen earned a slightly higher salary and usually escaped the chores. If a stable had no horses in a race, its contract jockeys were allowed to freelance for other barns. When riding for their contract stables, bug boys received nothing from the purses their horses won. Journeymen and freelancing bug boys earned $15 for a winner, $5 for every other placing, minus fees for laundry (50¢), valet ($1), and agent (10 percent) if they could afford one. Technically, freelancing jockeys were due a 10 percent cut of purses—usually about $40 at the better tracks where Pollard rode—and 50¢ for galloping horses in morning workouts, but almost no one paid it. The best journeymen negotiated for higher pay, and some tried to even things out for the struggling ones, offering to “save” or divide the winning purse among all the riders, but this was eventually made illegal as it removed the incentive for winning. In this system a tiny subset of riders became wealthy, a few lived comfortably, and the rest, the vast majority, had nothing.
The world of bug-boy jockeys was populated mostly by teenagers who had run away or been orphaned or whose families had come upon hard times, as Pollard’s had. “Every one of them would have a story,” recalls Mosbacher, who wound up at the track after running away from an impoverished home. Only a few had an elementary-school education, and none had made it through high school. Most had no place else to go. “I was hungry,” explained child bug boy Ralph Neves, who came to the races as an orphaned runaway, “and too nervous to steal.”16 By the rules, a boy had to be at least sixteen to ride, but no one ever asked for a birth certificate. Some riders started as young as twelve. During one 1920s season at the old Tijuana track, former rider Bill Buck remembered, the two oldest riders were just sixteen. Bug boys were often remarkably small; Wad Studley was so tiny when he started riding—eighty-two pounds—that he had trouble lifting his own saddle. On the day he rode his first winner, Tommy Luther weighed seventy-nine pounds. Most of these boys knew nothing of racing when they began and were completely at the mercy of their trainers.
Some trainers became surrogate parents to their bug boys. Others exploited their charges with relentless cruelty. Luther recalled that in some stables a bug boy’s punishment for losing a race was a stout beating. “Father” Bill Daly, a peg-legged trainer described by one writer as “villainous,” reportedly carried a barrel stave with him at all times so he could beat his jockeys.17 When they weighed too much, he reportedly cleaned their pockets of their pennies so they couldn’t buy food or locked them up until they starved down to the right weight. To avoid train fare, Luther and his fellow bug boys were stowed away in horse cars. When the railroad police came through the train, impaling the haystacks to flush out stowaways, the trainers packed the boys into tack trunks. On another occasion, a trainer put Luther up in a hotel, then booted him out the window when the bill came due.
On the track, bug boys were like any other commodity, to be leased, sold, swapped for horses, put up as collateral, and staked in card games. Though they earned practically nothing, they cou
ld be worth a lot, upwards of $15,000 for a good one. Many bug boys were sold without their knowledge. In 1928 jockey Johnny Longden learned of his change of ownership early one morning in Winnipeg, where his trainer had put him up in a tent. While he slept, a stranger walked up and began shaking the tent violently. “Get the hell out of here!” barked a voice from outside. “You’re working for me now, and nobody on my payroll sleeps late.”
Pollard was lucky. Acey treated him well. In the summer he usually raced at the cluster of tracks around Vancouver or at another western Canadian track called Glacier Park; in the fall and spring it was California’s Tanforan; in the winter, Tijuana. Pollard spent his days aboard Acey’s animals and his nights in a stall, sandwiched between two horses, subsisting on his books and irregular meals from the track kitchen.
Veteran horsemen were merciless to kids who wanted to be jockeys. A common prank was to send a new bug boy all over the track looking for the phantom “key to the quarter pole.” One kid who came to the track in Tijuana and announced he wanted to be a jockey was told he had to take off some weight. Horsemen draped him in two horse blankets and made him run around the track in 110-degree heat. They watched him make one trip down the track, reconsider his ambition, and keep right on going into town. They never saw him or their blankets again. Pollard got much the same treatment, but he was almost impossible to discourage. “Who hit you in the butt with a saddle and told you you could ride?” a starter hissed before a race.18 “The same S.O.B. that hit you in the butt and told you you could start!” he shot back. Pollard had found the one place on earth that could hold his interest. He was broke, hungry, and, according to his sister Edie, “happy as heck.”
He never lived in Edmonton again. His mother worried over his fate but hid it from her children. His father, eager to see him and furious with the man who had abandoned him, scraped together a few dollars and traveled all the way to Vancouver to stand in the crowd and watch his son ride. Thanks to the rigid rules governing bug boys, Pollard was not even allowed to turn his head to look at his father as he rode past. Never again would anyone in his family have the money to come see him.
Pollard struggled to find his place. In 1926 he had only eight mounts, winning with just one of them. But under Acey’s tutelage, he began to find his niche. In his first season in Tijuana he befriended a blind trainer named Jerry Duran, who was struggling to make something of a horse named Preservator.19 Devoid of talent—in three years and forty-six starts he had won just five races—Preservator was also a comparatively geriatric seven years old, roughly the equivalent of a human runner in his late thirties competing against twenty somethings. Duran brought Pollard on board as Preservator’s jockey. Seeing that Duran was incapable of handling many of the training duties, the seventeen-year-old took them on himself. In Pollard’s care, Preservator improved dramatically, winning six races and earning a respectable $3,170. After each race Pollard would read the official chart for Preservator’s performance out loud to Duran. When the horse ran poorly, Pollard skipped over the disappointing race notes and invented tales of Preservator’s impressive feats, dreaming of bad-luck excuses to account for the horse’s losses. His efforts heartened Duran and impressed other horsemen, who began to hire him. In 1927 he was assigned to ride more horses, and once in a while he won.
His small measure of success didn’t go unnoticed. After seeing Pollard booting Acey’s horses around Glacier Park, a horseman named Freddie Johnson contacted Acey and asked how much he wanted for the jockey. After a brief negotiation, a deal was struck. Pollard came cheap. For two saddles, a handful of bridles, and two sacks of oats, he became for all intents and purposes the property of Freddie Johnson.20 Johnson handed him over to his trainer, Russ McGirr.
McGirr soon discovered that Pollard had a rare skill. His natural empathy and experience with the horses of the bullring circuit had given him insight into the minds of ailing, nervous horses. He rode horses no one else was willing to go near. He had learned to keep his whip idle, compensating by riding with somewhat longer stirrups that allowed him to urge horses gently with his lower legs.21 The horses responded to his kind handling, relaxed under him, and tried their hardest. Under McGirr, Pollard became known as a specialist in rogues and troubled horses and began to win regularly with them. Because a large percentage of his mounts were claimers competing for tiny purses, Pollard didn’t earn much money. He mailed most of what little he did make to his father to help him hang on to the family house. The rest usually went out in “loans” to needy friends. Pollard was a pushover, and all the down-and-outers knew exactly where to go to pick up a few bucks. He never had the heart to ask for it back. “I never could,” he would later say in his odd way, “throw money around like glue.” But he was getting a lot of mounts and winning with almost 10 percent of them, so he got by. After two years in the saddle, it seemed that Pollard was going to make it.
On the backstretch at Lansdowne Park in the cool Vancouver summer of 1927, Red Pollard first saw George Monroe Woolf. He must have been quite a sight. Everything about Woolf spoke in the imperative. The first thing everyone noticed was the spectacular cowboy garb: ten-gallon spanking-white cowboy hats blocked porkpie style, weighty signet rings, smoked eyeglasses, fringed leather jackets, ornate breeches, gabardine shirts tailored to his powerful shoulders and dyed in a confusion of color, and hand-tooled cowboy boots embossed with animal images in real silver.22 Arrestingly handsome, George had dark blond hair that cruised back from a part he kept just a nudge off-center, as was the fashion. He held his chin up Mussolini-style, and the corners of his mouth turned up in a smothered smile, as if he knew something no one else did. He spoke in a slow, drizzling drawl, but his eyes were as clear and sharp as a cat’s. He decorated in frontier art, pored over western magazines, listened to Gene Autry on the phonograph, and motored around town in a blindingly ostentatious hot rod Studebaker roadster with a bug boy riding shotgun. Woolf, remembered former bug boy Sonny Greenberg, was “fabulous in everything he done.” In the summer of ’27 he was seventeen, aloof, clever, and utterly singular. He also may have been the greatest riding talent racing ever saw.
Woolf had the ideal pedigree for a jockey. His mother, Rose, was a mounted circus acrobat; his father, Henry, was a stagecoach driver and rancher who, George liked to say, “never had much money but always owned a fast horse and a fightin’ bulldog”; his brothers were both professional horse breakers.23 Accordingly, expectations for Woolf’s career in the saddle preceded him into the world.24 On May 31, 1910, in the wheat and cattle country of Cardston, Alberta, Rose was midway through her labor with George when her husband interrupted the doctor. How long, he asked, before he could put the child up on a horse? If the doctor counseled patience, his words didn’t leave an impression. While growing up in Cardston and later on the similarly broad scapes of Babb, Montana, Woolf couldn’t remember a time when his view of the world wasn’t framed by a set of horse’s ears. “Must have been born on one,” he mused.25 Riding, he said without exaggeration, “is as natural as walking to me.”26 He spent more of his youth on horseback than on foot. “Horses are in my blood,” he said. “I’ll be with them until I die.”27
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.28 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.”29 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.31 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.