The girls took customer service seriously. Velvet-Tongued Velma and Chi Chi Grande needed no introduction. A girl the riders called One Wing Annie did a brisk business despite missing one arm. One girl told a bug boy that if he could track down $5, she’d show him something he’d never forget. Five dollars was the kind of money you could live on for a week back then, but practical considerations were unlikely to occur to a bug boy in such a situation. Within moments, a herd of jockeys packed into a room at the mill and showered $5 worth of nickels and dimes on the girl in question. She promptly stripped naked, lit up a cigarette, and blew smoke rings from a place into which only a creative-minded and supple-bodied prostitute would think of placing a cigarette. It was the greatest day of the bug boys’ lives. “What talent!” recalled a witness. “Of course, I had to change my brand of cigarettes after that.”
The Molino Rojo set the standard for Tijuana. The jockeys lived high and hard, riding by day, roaming the town in dense, noisy scrums by night, pouring into the Molino Rojo, then the Turf Club saloon, then on to wild exploits in town, chasing giggling girls buck naked down motel corridors, stealing all the room keys to the town’s biggest hotel. Among the riders were Red Pollard and George Woolf. It was to this strangely bountiful place that they came each winter, and they thought of it as home. Riding there from fall to spring every year, they defined themselves as athletes and as men.
In 1928, their first full season together, they took the racing world by storm. Settling into his niche as a miracle worker for tough and neurotic horses, Pollard earned assignments on nearly three hundred mounts and guided them to more than $20,000 in total purse earnings. His fifty-three winners placed him in a tie for twentieth in winning percentage among fully employed riders in North America (those with one hundred or more mounts). He was a complete success. But Woolf was supernatural. Though in the big leagues only a few months, Woolf was signed on to ride more than 550 mounts, many of whom were stakes horses of the highest quality, and won with more than 100 of them for total purse earnings of $100,000. His winning average of 19 percent ranked him in a tie for sixteenth among fully employed riders. As the weekday wonder and the money man, Pollard and Woolf established themselves in the uppermost tier of North American racing.
They also carved out their own respective roles in the social world. Pollard, with his books, his stories, and his offbeat sense of humor, earned the bewildered affection of everyone at the track. A small cadre of racetrack eccentrics gathered around him. In the jockeys’ room he orchestrated a string of clever practical jokes, sequestered himself in corners to pore over literature, and mystified his fellow jocks with aphorisms from Omar Khayyám and “Old Waldo” Emerson. A passing incident might inspire him to gallop through huge sections of Shakespeare, committed to memory, leaving the bug boys furrowing their brows. His language was a patchwork of cultivated speech and blue-streak profanity. He was loved for his wicked humor, delivered with a Buster Keaton straight face, and boundless generosity. He was feared and admired for his fistfighting skills, drop-of-a-hat volatility, thundering bass voice, and daring.
He was a prolific yarn spinner. One tale featured Pollard riding racehorses for Czar Nicholas. He could slip this one past the bug boys, who hadn’t gone to school long enough to know that the Bolsheviks had put an end to poor Nicholas when Pollard was only nine. Another favorite described how he inadvertently bedded down beside five hibernating bears in a Canadian cave. Hair grew on this story until the bears were wide awake and the ex-boxer was using his deadly left hook to knock all five unconscious. When he wasn’t telling stories, he was smartassing racing officials. He once attended a racing banquet at which a racing starter was the keynote speaker. The starter was notorious for his profanity, specifically his trademark phrase “Put a twitch on that son of a bitch!” referring to a restraint device that was pulled over horses’ upper lips to distract them while they were being loaded into the gate. As the host droned through the starter’s introduction, Pollard fidgeted in the crowd, slurping up champagne and, like everyone else, stagnating in boredom. As the starter rose to speak, clearing his throat for effect, Pollard abruptly stood up. “Put a twitch on that son of a bitch!” he boomed.
In the rough-and-tumble world of the track, Pollard was something of a sheriff. Farrell Jones, who rode alongside Pollard, recalled a fight he got into with a veteran jockey in a dispute over a checkers match. When Jones won the match, the older jockey flipped the board across the room and promptly tackled him. Jones, who was only thirteen and weighed little more than eighty pounds, quickly found himself on the losing end of the tussle. The older jockey pounded him mercilessly and tried to jam his thumbs into his eyes. Pollard swept up to them, grabbed the attacking jockey by the back of the neck, tossed him to the ground, and pinned him. Pressing the jockey to the floor, he pinched his nose between his fingers and twisted it. The jockey howled for mercy. After letting him squirm for a while, Pollard released the rider, who had blood running from his nose and tears streaming down his face. “Don’t you ever touch that kid again,” Pollard hissed. He stalked off, leaving the room in silence. Nobody ever messed with Red.
If Pollard was the jester, Woolf was the king. The crowds adored him, shouting “Ride ’em, cowboy!” as he powered down the stretch on his good-luck piece, a battered kangaroo leather saddle once carried by Phar Lap, the greatest racehorse in Australian history. The press doted on him. The lost boys of the racetrack worshiped him. Woolf took them under his wing, letting them copilot his roadster and teaching them the fine arts of horsemanship. After winning races, he’d drive over to the backstretch and stuff cash into the pockets of his mounts’ grooms. He chaperoned groups of riders on mornings of road work, but by the end of the run discipline always seemed to break down and he’d end up jogging them into a gin joint to refill their depleted systems with a tall one. To help some of them conceal their big feet—and their coming growth spurts—Woolf started up a black market in his shoes. Riders all over the backstretch balled up their toes, wadded them into Woolf’s hand-me-down silver inlaid boots (which, to their misery, were pointed), and limped around in them all day. A jockey’s feet might bleed, but donning Woolf’s shoes was an honor. Horseman Harold Washburn’s boyhood memory of his first sight of Woolf sums up the impression the Iceman left on the kids of the backstretch. “I walked out and see Georgie pull up with that big car with them superchargers on it, step out of that car with them boots with silver inlaid on it, white western hat, and I thought, ‘Oh my God! I am going to be a jockey!’”
Woolf could get away with anything. In the spring of 1932, when a solar eclipse occurred just as he was scheduled to ride to the post, he carried a shaded glass out onto the horse with him, pulled up, lay his head back on his horse’s rump, and sat there, gazing at the sun while the crowd stared at him. In winning another race, he rode with such supreme concentration that he didn’t notice that he had torn right out of his paper-thin pants. He didn’t have a stitch of clothing on underneath, nor did he have the good fortune to at least be trailing the field. By the time he was galloping out, everyone at the track knew what Woolf had not yet noticed. “Hey Woolf!” came a laughing voice from behind. “You’re sticking out!” Woolf cantered the horse back to the cheering grandstand and calmly asked his valet for a saddle towel. The valet trotted up with the requisite fig leaf, and Woolf, smiling out of one side of his mouth, wrapped it around his waist, rode into the winner’s circle, and posed for the photo. He hopped down and glided back to the jocks’ room to a hearty round of applause.
Off the track, Woolf steered clear of the town’s appeals to vice, preferring late-morning pit stops in Checks Sloan’s restaurant for a complimentary beer and a bowl of turtle soup. Not even the Molino Rojo tempted him. He had better things on his mind. In 1930, while cruising up over the border with Sonny Greenberg, he stopped at a San Ysidro train-car diner and fell head over heels in love with a gorgeous sixteen-year-old waitress named Genevieve. Woolf began coming in regularly, parking his Stetson on the table and pointing Greenberg’s nose in the Racing Form while he romanced her. In 1931, at age twenty-one, Woolf married her.
Pollard, a more adventurous soul, probably lived a