Updated on 09/25/2013 8:49AM

Growing pains: The journey of an apprentice jockey

Four-Footed Fotos
Emmanuel Esquivel began riding on the Chicago circuit only this past February, but with his apprentice allowance he has rocketed to the top of the jockey standings at Arlington Park.

In December, the famed jockey schools of Latin America graduate their pupils. Their best young riders – the Joel Rosarios of the world – will have contracted agents to represent them in the United States. They leave soon after for south Florida or New York, their skills honed years for this chance, the circumstances of their departure carefully managed. They come ready to make money, ready to make their mark.

Emmanuel Esquivel’s jockey school was Hawthorne Race Course. He grew up in its backstretch dormitories, rode a pony around its barns, dropped out of high school to take a crash course there in galloping racehorses. In December, the Hawthorne track can freeze hard as pavement. The snow blows sideways off Lake Michigan. “You gallop in the cold,” Esquivel said, holding up his hands. “Frozen fingers.”

When Esquivel rode his first race at Hawthorne on Feb. 15, no one beyond a handful of entrenched Chicago horsemen had any idea who he was. No New York agents had called to take his book. But as the five-months-long race meeting at Arlington nears its end, Manny Esquivel has arrived, almost as if by magic, on the same career path as touted young jockeys coming through the pipeline from Latin America.

Esquivel enters the final racing days of the Arlington season as the meet’s leading jockey. He is North America’s third-leading apprentice by wins in 2013 with a chance to catch the top two by year’s end. He impresses trainers and fellow riders with his relaxed style and smart tactics, a dedicated sponge for knowledge, humble almost to a fault.

On the verge of a surprising riding title, Esquivel, like all successful young jocks, stands on the threshold of a long, lucrative career. But nothing is guaranteed. Apprentices like Esquivel, called “bug riders” because of the asterisk that denotes apprenticeship, are given a weight advantage over more experienced jockeys: In Illinois, the scale is 10 pounds for a new rider, seven pounds after five wins, five pounds after 35 wins. Those five pounds, many horsemen believe, can turn a tough loss into a narrow victory, and that weight break is the chief selling point of a bug rider. The end of apprenticeship – one year after the fifth victory in Illinois – sometimes marks the beginning of the end. Esquivel must properly manage his remaining apprentice months, deciding where he wants to be when his bug runs out in early March. He must balance the desire to win as many races and make as much money as he can right now with the need to continue growing and developing as a rider.

“A lot of people are asking me, ‘Where are you going? What are you going to do?’ But I haven’t really thought about it that much,” said Esquivel, who turned 23 on Sept. 9. “I just hope I finish this meet good.”

Esquivel understands his options. He could seek out quick cash. In New York, where horsemen love bugs, the purses are massive, even when racing declines later in the fall. There is big money at Keeneland, too. And one might think fast cash would be a flame consuming Esquivel’s thoughts.
Esquivel was born in Estepec, a village too small to make a map in the southern Mexican state of Guerrero. Esquivel, his parents, and three siblings came to Chicago when he was 8, settling into the Hawthorne community that spills into the predominantly Mexican-American village of Cicero. Esquivel’s maternal uncle, Cipriano Contreras, is a longtime assistant to trainer Mike Reavis, and he found Esquivel’s father, Josefat, work as a groom. The family never went hungry, but they were poor.

“When my dad got here, he had one pair of clothes, and he was with that pair of clothes for 15 days. In Mexico, we had nothing,” Esquivel said.

Esquivel is older than many of the jockey-school prodigies that come to the East Coast, and he is wiser and calmer than his numerical age, more grounded than the typical young rider. He has a steady girlfriend he says he wants to marry, and a young child. Some gifted riders are coddled, told they’re God’s gift to horseracing by people riding their coattails. Esquivel won’t think of himself as a rising star. For now, he is declining any invitations to Kentucky or New York. When Arlington ends, Esquivel goes back to Hawthorne, where racing will be conducted five days a week this fall and winter. Esquivel’s services will be in great demand.

“I just want to ride and ride and ride and ride. That’s the way you get better,” Esquivel said. “I’m not going to lie to you: I want to make as much money as I can. I think everyone wants that. But I want to learn as much as I can. I don’t want to just do this for two years, three years, or whatever. I want to do this for a long time, until my body gives up.”

Tough transition

The wreckage of promising riding careers is easy to find. There was a long stretch, between 2000 and 2008, when the Eclipse Award-winning apprentice rider made at least a modest mark after losing their bug, and 2006 winner Julien Leparoux won another Eclipse as North America’s outstanding rider just three years later. But the leading apprentices in North America regularly land on shaky ground.

“Every apprentice struggles when they lose their bug,” said longtime jockey agent Dennis Cooper, who has watched Esquivel up close this summer at Arlington. “People don’t remember it, but even Leparoux went right in the [toilet] when he lost his bug.”

One of Cooper’s Arlington riders, Eddie Castro, won the 2003 Eclipse as an apprentice after coming to Florida from a Panamanian jockey school. Castro is one of three such winners in the Arlington jockey colony: Rosemary Homeister finished second in the 1992 balloting, but the Eclipse winner that year, Jesus Bracho, later was found to have ridden too many winners in Venezuela to qualify for the honor.

Hall of Fame jockey Kent Desormeaux won an apprentice Eclipse in 1987, winning an amazing 450 races that year. But have you heard of Allen Stacy? He won the 1986 apprentice Eclipse, riding in Maryland, and Desormeaux knew all about him.
“He lost the bug and went from nine a day to no-no,” said Desormeaux.
Stacy’s post-Eclipse decline wasn’t quite that dramatic, but he won 207 fewer races his first year without the bug, and never rose above an 11-percent win rate during 11 years as a journeyman.

There are more recent examples, riders closer to Esquivel’s milieu. Alex Canchari came out of the blue to win the fall-winter 2012 riding title at Hawthorne, but though his business has rebounded this summer at Canterbury Park, Canchari went 12 for 181 when he tried his luck at Oaklawn Park this past winter. Freddie Lenclud was an Eclipse Award finalist for leading apprentice in 2010, when he won 83 races, and some thought he could be the next Leparoux, but he won two races in 2012 and hasn’t ridden at all in North America this year.

Desmormeaux and Homeister had a much different experience than Esquivel, though theirs were common. Both were whisked away from home not long after they began riding. Homeister started off hot at Calder in 1992 and quickly moved her base to Monmouth Park in New Jersey. The plan worked. Riding up and down the East Coast, Homeister won 172 races her first year. But make no mistake: There was a plan. Her mother, a trainer, and her connected agent knew prominent horsemen in New Jersey. The wheels were greased for Homeister to succeed.

“If you make the wrong move as an apprentice, you’re dead,” Homeister said. “You have to have everything set up the right way, and you need to get lucky right away.”

Desormeaux’s first race came at Evangeline Downs in 1986. He rode at Evangeline for one month and at Louisiana Downs for five weeks, and then trainer Dave Vance – who ran a large, highly successful outfit at the time – asked Desormeaux to go ride his horses in Maryland.

“It took about a month for me to get going there,” he said. “The first few weeks I just rode for Vance. I had a couple armchair rides that made me look smart, and everybody jumped on the wagon.”

Even with the right setup, a young rider can go off the rails. Tony Micallef is one of the New York agents who has represented talented, polished young jocks coming out of the Latin American schools. Micallef has booked mounts for Hector Rosario Jr., Fernando Jara, Ryan Curatolo, and most recently the highly successful Irad Ortiz Jr. When a bug boy starts winning in New York, there never is a question of talent. “They can’t come here and not look good on a horse,” Micallef said.

Talent, though, will only take a jock so far, especially when the weight allowance runs out. “It is very common for young riders with a high level of talent not to have the right mindset or work ethic,” said Micallef. “You can blow it all like that.”

“Your public skills are going to end up being as important as your skills on the racetrack,” said Desormeaux. “Sales management, what you do on the backside, what you do on your feet – that’s so much.”

In that area, Esquivel is set. He works as many horses as can fit into his schedule. He’s prompt and affable, his attitude gaining favor among trainers and other riders in the colony. “You can criticize him and it doesn’t bother him. He will make it in this business, just on his character,” Desormeaux said.

Patient rider

Esquivel had no road ready-paved for him when he started. His agent is Ben Allen, the nephew and former assistant to veteran trainer Bobby Springer. Allen knows everyone on the backside, is young, smart, and hard-working, but until this point, he never has been the guy with a jockey easy to sell at Arlington. But Allen had a longstanding relationship with Contreras, Esquivel’s uncle. And he happened to be one of the few agents out working at Hawthorne in the middle of last winter.
“Some of the more big-time agents aren’t at Hawthorne, especially in February,” Allen said. “Some people say Manny just fell into my lap, but I’d like to think a friendship with Cipriano as much as anything had something to do with it.”
Reavis put Esquivel on some well-meant runners at Hawthorne, but Esquivel didn’t have a major outfit entirely behind him, like Desormeaux in Maryland, or the automatic backing of trainers who knew he was starting out and had been looking for a competent bug. Esquivel won 29 races at the Hawthorne meet that ran from Feb. 15 to April 28, and a bettor who wagered on his every mount would have gotten back $2.22 for every $2 bet; Esquivel was guiding home horses who weren’t supposed to win.

And Esquivel was winning in a manner unlike most bug riders, who often are put on front-runners, eliminating the need for critical tactical decisions. Esquivel more often took up a spot somewhere behind the leaders, the horse beneath him relaxed and awaiting the jockey’s cue. This was the legacy of Esquivel’s earliest lessons as a gallop boy for the Reavis barn.  

The Reavis stable does things in a very particular manner: They ask for no speed in morning training. Their horses’ timed workouts always are among the slowest of the day. Galloping is performed similarly: Riders are not permitted to go fast, and this is the routine Esquivel mastered over the course of five years of galloping. It was not easy. At his maximum, when he ate whatever he wanted whenever he wanted, Esquivel weighed 120 pounds, the smallest exercise rider in the outfit. Contreras brought him to tears his first year when horses got away from him during routine training. Esquivel was forced to learn finesse, to coax a horse to relax, not wrestle him for control.

“He stays out of a horse’s way,” said Desormeaux. “A perfect passenger is one who can encourage a horse to rate without getting in his way, and he does that very well. And he’s a good tactician. He just knows where everyone is. Most apprentices don’t even know what the reins are for, but he’s cognizant of who’s around him.”

Esquivel quit high school at 16, and everyone was mad at him for it – his family, Reavis, his friends, his teachers. He said he earned perfect marks his final term at school, but the $700 or $800 a week he could make as a Hawthorne gallop boy seemed more important.

Here, Esquivel’s history runs parallel to the pipeline of apprentices coming up from Latin America: Many of these jockeys likewise gravitate to the racetrack as their best chance to escape poverty. And Esquivel also has faced an issue common to Latino riders: Born outside U.S. borders, he is not a U.S. citizen. Uncertainty over his immigration status delayed the start of his career, Esquivel said, and it wasn’t until President Barack Obama issued a directive to the U.S. Department of Homeland Security during the summer of 2012 changing the enforcement of immigration law, that Esquivel saw an opening.  

The wait gave Esquivel more time to hone his skills on horseback, important for a city kid who had no chance to learn to ride until he set out to gallop horses in the morning. That lack of long-term experience is one reason Esquivel doesn’t want to leave Chicago yet. He still is perfecting, for example, the art of switching his crop from hand to hand during the heat of a race. Neither he, nor his mentor, Contreras, believe Esquivel can yet be considered a finished rider.

“I just worry that if I go to New York or something it could break my heart,” Esquivel said. “You go there, you don’t do good, and that’s it. They got really good riders there, riders that’ve been riding for years and years. Thank God I’m doing good, but here people know me. I’ve been through every barn.
“Here it’s almost like family. Over there, they don’t know you; they don’t know if you’re a hard worker, and it takes time. By the time they get to know you, the meeting’s over, and what did you get to do? You didn’t do nothing.”

The agents and their associates have come calling from New York: Allen, Esquivel’s agent, will admit to this if Esquivel brushes it off. But Esquivel seems set in his decision to use his apprenticeship judiciously. There will be no grasping at celebrity, an early entrance onto a bright-lit stage. Esquivel still gets down to 110 pounds with minimal effort. Older Arlington jocks like Julio Felix have shooed him out of the hot box, where he had started going to lose weight this summer. Esquivel has returned to running in heavy clothes to shed whatever couple pounds need to go on race-day. Esquivel has a good chance to keep his weight in check. His personality is no fraud. He dearly wants to continue learning.

Many riders make a point of leaving Chicago as soon as Arlington ends. Hawthorne gets dark and cold early in autumn. The track sits in an industrial zone just southwest of Chicago proper. Esquivel knows its every nook and cranny. It’s where he wants to be this fall – home, where he thinks he needs to be to make it as a jockey.

** An earlier version of this article included a quotation saying Allen Stacy retired months after losing his apprentice allowance. Stacy rode for several years thereafter.

Apprentice Jockey Eclipse winners