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A Female Jockey Continues To Beat The Odds

Kayla Stra is a mother of two vying for recognition as a jockey

THE CROWD AT SANTA ANITA PARK TENSES, a collective in-breath, a moment for the bettor’s prayer or the devil’s bargain. Then pandemonium. Seven horses shoot out of the gate like bullets, and spectators spring to their feet in the grandstand. There’s money on the line. Bettors smack thick racing forms against plastic seatbacks, urging their favorites to the front. T-shirts and knit polos tighten over paunchy bellies as fans whoop and punch the air.

It’s the third race, a 1 1/16-mile endurance competition on a hallowed track for $20,000 in purse money. The horses gain speed and round the first turn in a close scrum. On the jumbotron, the brightly uniformed jockeys are like an electrified quilt gliding over the dirt. Then the leader separates, and the announcer barks a British staccato. A 29-1 longshot named Winninginfashion is out front. The jockey pushing the horse ahead is Kayla Stra—the only woman in any of today’s eight races, though it’s impossible to know that at a glance. In goggles and helmets, the tiny riders appear genderless. Horse racing is one of the few sports that doesn’t separate men from women—that’s because a jockey’s primary talent isn’t brute strength, but balance. It takes remarkable control to stay centered in stirrups over 1,200 pounds of charging muscle. It also takes remarkable balance to sustain a career in horse racing, one of the most physically dangerous and financially unstable sports in the world.

After a stunning debut 14 years ago followed by a sharp decline, which included a suicide attempt, rehab, and the more recent challenge of raising two young children with her partner Gus Headley, Stra is trying to find that balance. For a jockey to win, she must choose her moment carefully. As her horse Winninginfashion kicks dirt into the faces of its challengers, the few bettors who bothered putting money on the longshot are screaming for a miracle. Stra is setting the pace—but can she beat the odds?

Time Until Race: 6 Hours
Odds: 10-1

LIKE AN ACTOR OR POLITICIAN, jockeys put their trust in a rotating crew of paid advocates, including horse trainers, agents, and accountants. But the key to winning is finding a great “mount”—or racehorse. “They’re the real athletes,” Stra says, “and they need to work out to stay in shape, same as people.” The 31-year-old Australian is at the barns at Santa Anita Park several hours before her race to work out a horse for third-generation trainer Matt Chew. Trainers are hired by wealthy horse owners to take care of thoroughbreds and enter them in races. In turn, trainers use jockeys to work out their animals because jockeys know how to ride at high speed without losing control. “Matt’s been really good to me,” Stra says, clutching a travel mug of coffee and blinking sleep out of her eyes. “We’ve been working together for something like nine years. We’re friends.” Even so, Stra is here to hustle. By throwing Chew some free labor, helping him work out the thoroughbreds he’s paid to train, she’s hoping he’ll eventually select her to ride when he enters the horses in races. “You sort of do favors for people,” she says, “and hope they’ll remember you for it when it counts.”

Like everyone in her profession, Stra is a freelancer, a mercenary in an elaborate system that’s steeped in tradition and gilded with lore, but still operates like any job in the modern gig economy. Relationships are forged through savvy networking, and careers are built by taking big risks at the right time. There’s no safety net for jockeys—if they get injured, which is common, or don’t get named to a horse by a trainer, they don’t bring home their cut of the purse money (roughly 10 percent). But the upside is huge. Top jockeys make millions. In March, jockey Victor Espinoza guided California Chrome to an easy victory in the Dubai World Cup and grossed himself a quick $600,000. Not bad for two minutes’ work.

Santa Anita Park sits at the base of the San Gabriel Mountains, 20 miles east of Hollywood. As with everything in this sport, the track’s picturesque beauty is for sale—it’s been dolled up dozens of times for TV and films like Seabiscuit, and the people who work here are used to cameras and arc lights. The horses are led by grooms, with trainers walking alongside snapping orders to riders who look so small on their mounts they’re like ornaments on a Roman warrior’s helmet. “These are my coworkers,” Stra says. “We support each other. It’s like siblings—competitive, but it’s all family when it counts.” Stra is elfin at just over five feet tall—average for jockeys—with large brown eyes and dark hair that’s cropped short enough to disappear beneath her riding helmet. She walks in quick bird-like strides that betray an impatience with the baseline rhythms of this world. “You have to love speed if you’re a jockey. You can’t be afraid of anything.” Lately, she’s been working to manage those careening impulses off the track. Jockeys have a well-earned reputation for self-destruction, and Stra is no exception. But she’s a mother now—her daughter is less than a year old, and her son is nearly four. “I’ve learned to keep a general balance in my life,” she says. “I try to feel the same at all times.”

Chew, who has silver hair and the reposed, surveying face of a wise baseball coach, emerges from the shadows of the barn. He wants Stra to take a bay-colored mare named Cacica Dulima five furlongs, a little less than two-thirds of a mile, at medium speed. The horse’s eyes dart in the sunlight as it’s led out of the barn. Thick, branching veins in its legs and thighs pulse over muscles that ripple beneath a stunning coat. Stra rubs Cacica Dulima’s shoulder and leans in conspiratorially. “You have to listen to horses because they’ll tell you when there’s a problem,” she says.

“The first race I rode in professionally, the horse broke its leg. I knew something was wrong, I could feel it, but I didn’t let up.” A lame thoroughbred is untenable on a balance sheet. The horse had to be shot and dragged off the track. “I just walked away and didn’t look back. I promised I would never ignore what a horse was telling me again.”

Stra began racing in her hometown of Adelaide, Australia, when she was a troubled 17-year- old with a growing drug problem. “Everything except needles. Whatever I could get my hands on.” Racing gave her a place to focus her restless energy. “I didn’t feel scared when I was riding in races. I guess it was the only time I ever really felt peace.” She racked up wins and became one of the most promising young jockeys in the country. But she wanted more.

[quote position="full" is_quote="true"]Like everyone in her profession, Stra is a freelancer, a mercenary in an elaborate system that’s steeped in tradition and gilded with lore, but still operates like any job in the modern gig economy.[/quote]

At 24, Stra moved to Southern California, professional racing’s holy ground. The transition didn’t go well. With big purses on the line, Santa Anita Park is one of the most competitive tracks in the world, and her Australian resume didn’t carry weight. Her only chances came on poor prospects with no hope of placing. Horse betting is pari-mutuel, which means bettors compete against each other and not against the house. The racing form contains odds for each horse based on a mathematical assessment of past performances, but when the betting starts, the odds on the board change the same way stocks do. If bettors don’t back a horse, its odds worsen. By race time, the odds become a reflection of how well the betting public thinks a horse and its jockey will actually finish. Stra’s mounts were never favored in the racing forms, and the odds always got worse during betting, an indication that virtually no one was putting money on her. It’s the exacting way the community judges a rider.

“My whole life and my entire personality were wrapped up in racing,” Stra says. “I felt like I was failing at the only thing I was. I couldn’t see past it.” Her depression grew worse. She took a handful of pills from her roommate’s medicine cabinet and slit her wrists, hoping she wouldn’t wake up. She doesn’t remember much about the episode, but she came to in the hospital. Groggy from the drugs, she checked herself out and drove six hours north to Golden Gate Fields, where a trainer had offered her a handful of mounts in small-purse races a few days prior. “I remember I almost didn’t make it in time. I went right from the hospital. I was late, and I was speeding and thinking that if I didn’t make it, then I wouldn’t know who I was. I would lose myself.”

She arrived just before post time—when jockeys have to be at the starting gate—and stayed in Northern California for two years. Riding against lighter competition, Stra started to win. She got medical treatment for depression and began doing yoga. “It was the first time I ever felt any kind of balance off of a horse.” In 2010, she earned horse owners over $1 million in purse money. Her success attracted attention down south, and she started riding the big tracks again—Santa Anita, Del Mar. When Stra got pregnant in 2012, she raced through her first trimester. “I didn’t tell anyone for awhile,” she says. “People got really upset about it.” Racing is tremendously dangerous for jockeys, and an accident could have jeopardized her pregnancy. “I was careful with the horses I took,” she maintains. Stra was back racing eight weeks after her son was born. After another break last year to give birth to her daughter, Stra is once again on the comeback trail—building up her reputation, putting herself in front of trainers. Jockeys survive on name recognition. “When you’re gone, people forget about you. So you have to start again and remind them what you can do.”

After some stretching to limber up, Stra is helped by an assistant into the thin racing saddle strapped to Cacica Dulima’s back. Then she and the horse begin their short walk to the track. To minimize the risk of injuring the horse during the workout, Chew instructs her to keep the pace below a dead sprint. Leaning against the outside rail that runs along the straightaway, the trainer watches Stra and Cacica Dulima fly by. “She did that a little too fast,” he says, pressing stop on his timer. His eyebrows rise just enough to express both humor and exasperation. “Just a little too fast,” he repeats.

Time Until Race: 4 Hours
Odds: 14-1

STRA’S AGENT, KEN HUTH, arrives after the workout. Huth is a handsome, fast-talking hustler in his mid-50s who looks like he could win a fight, but dresses like he belongs ring-side. He has a soul patch and wears a watch studded with diamonds he insists are real. When he points out horses, his pinky ring glints in the sun. He had the ring made back when he was playing minor league baseball in the ’80s. The design is his own, a heavy setting that cradles an old gold crown that fell from his molar. “I thought it would be kind of interesting,” he says, “something you don’t see every day.” Along with the watch, the ring has become a talisman on race days. “It’s got good energy.” He rubs his hands together and grins.

Huth has been representing Stra for a few months. “She wanted to make a fresh start after the baby, so she called and asked if I would take her book. I would have loved to represent her a few years ago, but she was signed with a friend of mine and it’s not cool to poach.” In the United States, jockeys pay agents 25 percent of all earnings in exchange for help networking with trainers and setting up the morning workout sessions that lead to mounts. “Kayla understands she has to show up in the morning if she wants to make money in the afternoon. Some jockeys don’t get it, but she’s hungry,” he says. “I think she could make some big money if we get her on decent horses. People overlook her, maybe because she’s a woman, but she always finishes strong. You could make a lot of money betting on Kayla Stra.”

Unlike other major sports, which derive revenue from some amalgam of ticket sales, merchandising, and broadcasting agreements, horse racing is nurtured by a single nancial inlet: the betting window. The track takes a percentage known as the “takeout.” That money pays facility fees and funds the purses that entice horse owners to enter their exceedingly expensive pets in an exceptionally precarious competition. “That’s where jockeys make your money—on the track,” says Huth. “They get a guaranteed fee every time they race, like a hundred bucks, but owners also give them a percentage of the purse money when they win.” In addition to the agent’s cut, jockeys pay a small percentage of their earnings to their valet, a kind of race-day assistant who manages a jockey’s uniform. Jockeys also tip the grooms and stable hands who help maintain the horses they ride. Win or lose, a jockey will pay out 30 percent of earnings before taxes.

The purse in the first race today is $25,000. The owner of the winning horse gets 60 percent of that money, or $15,000, with smaller sums going to the second and third place finishers. Jockeys get 10 percent of any purse money they win. After paying an agent and a valet and tipping the groom, the winning jockey will be left with $1,050 before taxes. Earnings fall precipitously for jockeys who don’t come in first. If a horse doesn’t show in a race, anything fourth place and below, the jockey will collect the standard mount fee, about a hundred bucks. Most jockeys are lucky to win 12 percent of the time, and at competitive tracks like Santa Anita, where the purses are larger, the competition is more intense.

“It’s kind of a Catch-22,” says Stra’s business manager and accountant, Bob Croasdale, who’s tall but beginning to gently slouch in his mid-50s. Croasdale wears a baseball cap and round clip-on sunglasses as he stands beside a circular pen where the horses and jockeys in the first race are taking a preening lap. “Jockeys can’t get the best horses unless they prove they can win, but they can’t win unless they get good mounts. That’s really what’s kept Kayla back her entire career.”

The horses are led out of the pen toward a tunnel that will take them to the track, the jockeys in uniforms as brilliant as candy shells. Croasdale has spent hundreds of hours devising a system to evaluate jockeys that goes deeper than simple winning percentages. Geeking out on racing metrics, he calculated how the horses Stra rode in 600 recent races should have finished based on statistical expectations. When he compared the gures to the actual race results, he found that she met or beat expectations 58 percent of the time. “I read the data to say that she pulls as much out of a horse as it’s capable of giving. If she gets good horses, she’s going to win races. The numbers don’t lie about that.”

Time Until Race: 2 Hours
Odds: 20-1

CONCESSIONAIRES ARE DOLING out hot dogs and beer. The tractor-tilled soil on the mile-long oval looks loamy and fresh. The Friday crowd is sparse, though the faithful gather in the stands and talk boisterously. Decades ago, Santa Anita used to draw 20,000 to 30,000 fans with regularity. Now the turnstiles are lucky to tick past 5,000 on a weekday. Many of the hardcore bettors are still in the Paddock Room, a betting parlor with a low ceiling in the belly of the grandstand where matrices of televisions simulcast races from around the country. The walls are lined with automated betting machines, but traditionalists have queued up at open windows to read their picks to human tellers. The crowd here is racially diverse and uniformly old. The sport has not bridged the generational divide. Horse racing culture used to be the embodiment of cool—Bing Crosby and Gary Cooper were among the founders of the Del Mar track when those two were the hippest things going. Race day fashion once kept a cottage industry of dressmakers, tailors, cordwainers, and milliners busy from spring until fall. I ask a parking attendant if any celebrities still make it to Santa Anita Park. “Oh, without a doubt,” he says, rattling off a few names. Joe Pesci deservedly gets top billing.

The first race is uneventful—a horse named Miss Bliss takes it by five lengths—and the grandstand crowd uses the break that follows to refill beers and place more bets. There are eight races on today’s program, and the self-styled professional bettors have been here since early this morning. One portly gentleman named Jimmy holds dominion over a patio table at the base of the grandstand, where he has been sitting since Stra’s early morning workout. His racing paraphernalia is neatly arranged on the rippled glass table-top: reading glasses, racing form, blue and black Sharpies, electric pink and yellow skinny highlighters, a couple of pens. He is hefty, maybe 300 pounds, with a broad bulldog face and thinning hair buzzed into a squared-off military cut. “There are some good women jockeys, don’t get me wrong,” he says, “but a lot of them can’t finish. They’re not strong enough to bring the whip down when it counts.”

The paradox of horse racing is that it’s ruthlessly results-driven, which has opened up opportunities for women like Stra to compete head-to-head with men. But at the same time, it’s lousy with old sensibilities and pigheaded beliefs. In 1969, Diane Crump, then 20, became the first female jockey to compete professionally in North America after she was led from her makeshift jockeys’ room to the horse enclosure at Florida’s Hialeah Park Race Track under armed guard. A syndicate of women tried to break into racing for a couple of years. There were lawsuits and petitions, and Crump’s chance came after two other female riders were boycotted at the starting gate by male jockeys. “It was like a freak show,” Crump recalls from her home in Virginia. A crowd of curious race fans swelled around her as the guards shoved out a narrow path. “It was just that people didn’t think women could do it. It seems strange, doesn’t it, in this era?”

Horse racing got its first female superstar in 1993 when Julie Krone won the Belmont Stakes, one of the biggest races in the country. She made it to the cover of Sports Illustrated and became a frequent guest on talk shows. “Julie Krone opened up the sport for so many girls,” says Chris Forbes, a horse racing historian. “People saw her competing at the highest level, and that set a lot of careers in motion.” By the time Stra was starting in the early 2000s, female jockeys were definitely in the minority, but no longer an oddity. Today, tracks have male and female jockeys’ rooms, and most male riders have come around to the idea of racing against women. Old attitudes still surface from time to time, though. In 2013, a race official banned Stra from the jockeys’ room at the now-defunct Betfair Hollywood Park for breastfeeding her infant son. “It was such a strange thing,” she says. “It wasn’t a big deal to anyone, but he felt like he had to take a stand.” California Horse Racing Board chairman David Israel intervened, quickly overturning the ban and assuring female jockeys they can breastfeed anywhere they like. Stra’s own feelings about being a woman in a world that can feel hopelessly anachronistic have changed.

“I used to try to blend in and not call attention to the fact that I’m a woman,” she says. “Now I think it’s kind of an advantage. It helps me stand out, which is important.”

Drinking a plastic cup full of Pepsi at his patio table, Jimmy concedes one thing. Women, he says, “are better in some ways because they have maternal feelings. They can deal with the horses, I mean.” I can almost hear the mechanical click in his bettor’s brain when I remind him that Stra just had a baby. “Hey, that’s right. And she’s been running pretty good.” His eyes return to his racing form as he sizes up the field of horses and jockeys in the third race one more time.

Time Until Race: 5 Minutes
Odds: 28-1

“I THINK WE GOT A SHOT IN THIS ONE,” says Huth, pacing below the grandstand in the anxious moments before Stra’s race. The odds on the big board tell a less optimistic story. Croasdale isn’t so sure either. The business manager and accountant has volunteered to watch Stra’s son, Brys, while she races and he’s been chasing the kid around the grandstand ever since Stra handed him off and hurried into the jockeys’ room. He’s finally coaxed the kid to the fence to see Mommy ride. “It’s not a good horse,” he says. He’s a numbers man, and he’s been swayed by the form, which contains a wealth of statistical information about the horses that run each race. Winninginfashion was a 10-1 shot coming in, the second-to-worst odds in the field. But bettors have made the odds even worse. When the windows close, the horse and Stra are a dismal 29-1.

But numbers only count for so much. Huth prefers to live by his gut. As the horses enter the starting gate, the agent absentmindedly fiddles with his lucky timepiece. Attuned to the rhythms of race day, the crowd grows quiet. The palm trees sway in the unnaturally green infield against a cloudless sky and the drought-brown backdrop of the San Gabriel Mountains. It’s a Kodachrome portrait of one of the nest racetracks in the country.

[quote position="full" is_quote="true"]Horse racing is ruthlessly results-driven, which has opened up opportunities for women to compete head-to-head with men. At the same time, it’s lousy with old sensibilities and pigheaded beliefs.[/quote]

And then they’re off. Stra takes the lead and the surging pack rounds the first turn. An early lead in a 1 1/16-mile race is troublesome, since a sprinting horse may tire too soon, but this is the game plan. “Get out early and set the pace, then take it all the way!” shouts Huth.

“She did the half in 47 seconds,” Croasdale retorts, looking a little queasy. “That’s too fast.” He’s worried she’s pushing Winninginfashion too hard—an unproven horse at a dead sprint is bound to fade. If Stra keeps that pace, she and her horse will lose.

The jockeys are bunched close enough to smell each other’s breath. If a horse goes down, its jockey is liable to be trampled. Stra’s son is nosed up against the fence. “They’re going to finish right in front of us,” Croasdale yells over the crowd, which now seems possessed. Adult men and women have sloughed decorum and seem to entreat exotic deities. “Come on, Odisseia!” “Come on, Amberella!” “Come on, Winninginfashion!”

Stra lets up imperceptibly, and the pack closes behind her. A jockey is only as good as her mount. She can feel the bellows of the animal’s lungs. She can feel the horse’s energy dwindling. She feathers the mare’s shoulder with her whip. One rider edges past her on the outside, and then another. Two others threaten to knock her out of contention. She waits. She has to summon her horse’s strength for a final burst. She has to pick her moment. The odds are set. The bettors are screaming. This is the calculus of horse racing.

Stra twirls the whip in her hand and raises it high over her head like a majorette’s baton. Then she begins bringing it down with a new rhythm. “Come on, baby!” screams Croasdale. He is no longer a numbers man; now he is a believer. Winninginfashion surges to retake second in the final stretch. “Come on, baby!” screams Huth. The horse is giving Stra everything its got. “Get away, get away!” Statistically, Winninginfashion should finish sixth. Stra crosses the finish line. She’s a close second.

“Look at that!” yells Croasdale. “Classic Kayla Stra, that is classic! You give her a horse nobody thinks has a chance, and she gets everything she can out of it! God, she can ride.”

The crowd is quiet now. Gray-haired spectators file out to collect their earnings, place new bets, and bring back food. After three races, losing tickets litter the grandstand. The winning horse, Warren’s Tricia R, stands in the winner’s circle glistening with sweat. Beside the mare are a beaming owner and a proud jockey. Huth and Croasdale head to the tunnel beneath the grandstand to congratulate Stra.

“It was all right,” she says of her race. “I almost had him at the end.” Croasdale props Brys up on the fence, and Stra kisses her son. Then she gives a quick interview for a camera crew and heads to the jockeys’ room. Her second-place finish earns her $400. After paying Huth and her valet, she will keep $280. A modest sum, but her impressive showing has given her a real shot at a comeback. The trainers at Santa Anita obsess over results, and Stra has beaten the odds yet again. Not bad for two minutes’ work.

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