04/11/2013 12:00PM

Switching gears: Jockeys turned trainers face tough transition

Shigeki Kikkawa
Hall of Fame jockey Gary Stevens started a new career as a trainer in 2009, but the pressures of the job forced him to disband his stable less than a year later.

Seventy years ago, in what was called the “Streetcar Derby” because of wartime restrictions on travel, Johnny Longden rode Count Fleet to victory in the Kentucky Derby. Longden also rode the medium-sized, headstrong colt to wins in the Preakness and Belmont Stakes, making Count Fleet the sixth of what has become 11 Triple Crown winners.

Twenty-six years later, and three years into a training career, Longden brought the undefeated Majestic Prince to Churchill Downs, where Bill Hartack rode him to victory in the Derby. While Majestic Prince, after winning the 1969 Preakness, came up short against Arts and Letters in the 1969 Belmont, the defeat didn’t detract from Longden’s Derby double − he was, and still is, the only horseman to ever win the race as both a jockey and a trainer.

Seven times before Longden’s incredible feat, but only twice since, has a Derby-winning jockey had the chance to also win the race as a trainer. Historical happenstance? Perhaps, but a better observation is that not as many high-profile jockeys, like Longden, follow the game into the training ranks anymore. Maybe, because of inflated purses, many of the big-name jockeys bank enough money to tide them over during their retirement years. Or maybe it’s because training has become a more complicated game than it used to be. Whatever the grab-bag of reasons, trainers are much more likely to come from within their own fraternity than they are from the riding colonies. All evidence is anecdotal, because statistics on such a thing would be impossible to research, but the likeliest feeder system for trainers these days is assistant trainers trying to move themselves up.

As for jockeys making the transition to training, no one seemed more qualified than Gary Stevens. The son of a trainer, and a Hall of Fame rider with almost 5,000 wins, he launched a modest stable in the summer of 2009. About nine months later, with mixed feelings, he moved on.

“The bureaucracy of racing wore me down in a hurry,” Stevens said. “Dealing with owners. Worrying about medication. I lived in fear that a groom might get something on his hands, and I’d have a horse test positive by contamination, and then where would my reputation be? You hire people to do all the various things around a barn, but the bottom line is that it all gets back to you if something goes wrong.”

Stevens had worked as an assistant trainer in 2000 and studied assiduously the numerous Hall of Fame trainers whom he rode for. In early 2010, less than a year into training, he turned in his license and sent his horses to other barns.

“Training was spreading me too thin,” he said then. He had never stopped on a broadcasting career, and though HRTV had set up a schedule that worked around his job at the track, he decided eventually to focus on television. 

“I only won one race,” Stevens said, “but I was proud of the fact that after they left my barn, five of those horses won their races with other trainers in the next six days. I just didn’t need the pressure. One of the biggest drawbacks was collecting money from clients. Some of my owners were always two months behind in paying their bills, and it seemed like I was forever behind the eight-ball. There was always the feed guys showing up, wondering when they would be paid.”

Angel Cordero, another Hall of Fame jockey, left riding grudgingly in 1992. The wakeup call, at age 50 after 7,057 wins, was a four-horse spill at Aqueduct in which he broke an arm, three ribs and suffered kidney and spleen damage. His wife, Marjorie, was already training a 15-horse stable and Cordero said: “I only hope I accomplish as much training as I did riding.”

Although he had lineage on his side – his father and both of his grandfathers were part of a lengthy training heritage in Puerto Rico − Cordero was kidding himself. In the saddle, he had won the Kentucky Derby three times and four Breeders’ Cup races. He had left himself with too tough of an act to follow.

“It was a big change in a short period of time,” said Cordero, who quit training several years later. “I did all right for the horses I got. You’re only as good as the horses you get, and I didn’t get the big clients that I thought I would get.”

Had his stock been better, Cordero had a built-in advantage that many jockeys can have: The ability to exercise their own horses. Bill Shoemaker, before an automobile accident left him a quadriplegic, had that edge as a trainer. So did Johnny Longden. Two days before Majestic Prince’s Kentucky Derby, Longden worked the colt five furlongs in an obscenely quick 58 3/5 seconds, which prompted the naysayers to dismiss the horse. But Longden wasn’t concerned.

“I know what to do with Majestic Prince,” he said at the time. “When I get on him, I know how he is.”

[CLOSER LOOK: Five jockeys turned trainers who made it, five who didn't]

Like Cordero, Longden went from riding to training overnight, but with far better results. The difference was that Cordero didn’t have a Frank McMahon in the wings, ready to give a new trainer his close-up. McMahon, a wealthy Canadian oil driller, was responsible for jump-starting Longden’s second career. Three days after Longden’s final mount – and 6,032nd career win -- with George Royal in the 1966 San Juan Capistrano at Santa Anita, he flew to West Palm Beach, Fla., where McMahon was wintering.

“Most people think I had the job all lined up before I retired,” Longden told his biographer, B.K. Beckwith. “That’s not true. There might have been some vague talk about it before, but the offer didn’t come until . . . I hung up my tack.”

After his meeting with McMahon, Longden returned to California. On opening day at Hollywood Park, with the first horse he ever saddled, Longden won a race with McMahon’s Attention III, Bill Shoemaker aboard.

“Training’s a lot harder,” Longden said not long after he had made the switch. “There are longer hours, and more responsibility. If a horse goes wrong when you are riding him, you simply get on another. Not when you’re training him, though. Then he’s in your barn, an ever-present worry, and it’s up to you to get him back running again.”

Longden was 59 when he quit riding. Wayne Catalano was 27. By 1983, Catalano had already won 1,792 races as a jockey, including 349 in 1977, when he was a distant second to young Steve Cauthen’s 477. Longden’s retirement announcement, which had been rumored for years, came a couple of days before George Royal’s dramatic win. Catalano’s quitting was even more abrupt. One day at Sportsman’s Park, he took off his size-6 1/2 boots and never put them on again. His knee surgery a few years before had been successful, sort of.

“I was a hands-on jockey,” said Catalano, who as a trainer has won three Breeders’ Cup races and been Arlington Park’s leading conditioner 11 times. “The last three or four years, I wouldn’t just ride horses and go home. I would go back to [trainer Jack Van Berg’s barn] and help out. Jack is a great horseman and a great trainer, and then when it came time to switch over, he asked his main client, John Franks, if he’d give a few horses to get started.”

Actually, Catalano’s tutelage under Van Berg started earlier than that. Before he was old enough to ride, he had shown up at Van Berg’s barn at the Fair Grounds in New Orleans, where Catalano grew up. He became a hotwalker and groom along with another aspiring racetracker, Frank Brothers.

“Frankie and I fought to see which of us had the most winners when we were both grooms,” Catalano said. “Frankie was very ambitious. He would get there at 3:30 in the morning, ahead of everybody else. He was preparing to be a trainer and I was in the early days of learning to be a jockey.”

Catalano rode his first winner in 1974. Nine years later, he set out on his own as a trainer.

“Before that,” Catalano said, “Jack showed a lot of faith in me. One year he sent me to Keeneland with a lot of his horses, and we won a lot of races.”

By the time Catalano was ready to train his own string, he was fully versed.

“You don’t see many jockeys going this route, because they’re not used to all the hours,” Catalano said. “It’s 365 days a year, and it’s a lifetime commitment. You’ve got to be there every morning. It’s a tough job.”

The jockeys’ curse hit Wesley Ward in spades in 1989, only five years after he had won 335 races and been voted the Eclipse Award for best apprentice in the country. Ward, who was 16, weighed 100 pounds then; now, he’s a couple of inches taller, but he also weighs 180. Like his father, Dennis Ward, an overweight Wesley also moved into training, and racked up his 1,000th win as a conditioner in 2011. Two years before, he took six young horses to Royal Ascot and won with two of them, becoming the first U.S.-based trainer to win at England’s marquee meet.

“It wasn’t definite that I would follow my dad into training,” said Ward, who moved his stable from California to Florida several years ago. “From the start, I knew I would eventually have a weight issue as a rider, but it came far sooner than I thought. I got very depressed when I couldn’t ride anymore. My first plan was to become a steward. I was accepted by the racetrack management program at the University of Arizona, but then I realized that watching races was only a small part of a steward’s job. More than anything, it’s an office job. So I went with my dad as an assistant, then eventually got my own license.”

Ward asked a lot of questions of trainers when he rode, preparing himself for what might be down the road. But clients were slow in signing up, and he was stymied for a time at tiny Yakima Meadows, in his home state of Washington, surrounded by $2,500 claimers. By the time he made the jump to the big leagues at Santa Anita, his stable didn’t even fill up one side of a shedrow, but he foresaw one colt as the breakout horse.

“He was a beauty,” Ward said. “We had gotten him for $10,000 at a sale. I looked at him and said, ‘This is the one.’ I was patient with him. My aunt, Linda Baze, was his exercise rider, and she took very good care of him. Finally, there was a maiden race coming up, and I was sure he was ready. I led him over [to the paddock], very proud. He was going to go off at about 60-1, but I thought he was a cinch. I put $100 on his nose. Well, he got beat by 35 lengths. He wound up back at Yakima, running for $5,000, the following winter. That was the eye-opener for me in this business, and brought me down to the level where I belonged. I still had a rider’s mind, winning races all the time, but when it comes to riding and training, you’re talking about two different worlds.”

Echoing Gary Stevens, Ward said one of the hardest jobs for a trainer is getting bills paid.

“If I had all the money I was owed, money I know I’m never going to see, I’d be able to go live on a desert island somewhere,” he said.

In 2011, two years after his invasion at Royal Ascot, Ward became the first U.S. trainer to saddle a winner at Longchamp, in Paris. This is the Longchamp where Freddie Head rode four winners of the Arc de Triomphe, France’s mirror image of the Kentucky Derby. Since he quit riding in 1997, at age 50, Head has become one of France’s pre-eminent trainers. Punters who have seen him over here will readily second the motion. When Head won the Breeders’ Cup Mile with Goldikova three times, he became the first horseman to both ride and train Breeders’ Cup winners. His riding wins in the Breeders’ Cup came with another crackerjack filly, Miesque, in the 1987 and 1988 Mile.

A couple of years before he quit riding, the 65-year-old Head bought a training ground in Chantilly that had room to stable 100 horses. His father, Alec Head, had been a French training champion, and his sister, Criquette, also went into training, so Freddie’s future hardly needed a blueprint.

“I always knew I was going to train,” he once told Brough Scott, the British journalist. “But while there were plenty of promises, not many people sent me horses. People say all those things about top jockeys making trainers, and it’s difficult. That’s why I am so grateful to Sheikh Hamdan because he sent me horses from the very beginning.”

While joking with Scott that three marriages and seven children left him no choice but to go on working, Head reflected on his successes in the U.S.

“How impossible is that?” he said. “To be involved with two fillies as good as that? To ride one to win two Breeders’ Cups, to train the other to win three? It must be a billion-to-one chance.”

Since Longden completed the Derby double with Majestic Prince in 1969, only two jockey-trainers have had the chance to match him: Bill Shoemaker, who rode three Derby winners and trained 1993 Derby starter Diazo, and Dave Erb, who rode Needles to his Derby win in 1956, then returned as a trainer to saddle a longshot, Helio Rise, in 1971.

In 1955, two months after Swaps’s Derby win and 11 weeks before he was beaten in Chicago by Nashua in the Homeric match race, Shoemaker was sitting out a stewards’ suspension, and Erb got the chance to ride Rex Ellsworth’s colt in the Californian at Hollywood Park. Running against older horses for the first time, Swaps got an 11-pound break in the weights and beat Determine, the 1954 Derby winner. The colt set a world’s record for 1 1/16 miles without ever feeling the touch of Erb’s whip. Shoemaker got back on Swaps in his next race and never left him.

Erb never left Needles, once he got his chance. He rode him for his last 11 races, including the wins in the Derby and Belmont. Five years later, Erb’s riding career was over.

“I wasn’t 40 yet, but I had been at it for 22 years and just got tired of all the reducing,” said Erb, 89. “I didn’t want to become a steward. In those days, at least, those jobs were too politically connected. I could have been a steward in Chicago. But I turned it down and they gave it to Ted Atkinson. There was a man in New Orleans, Roger Wilson, who had made his money in oil. I had ridden a lot of horses for him, and now he wanted me to train them.”

Erb and Wilson were together for more than a decade. They had only one argument.

“Getting along with the owners is an important part of it,” Erb said. “We had this real good colt, Hurry to Market, but he had bad feet, and at a time when they were really hurting him, Mr. Wilson insisted that I run him. We were 2 to 5, but we never had a chance. The crowd at the Fair Grounds threw bottles at us as we walked off. ‘I’ll never doubt you about a horse again,’ he said to me back at the barn.”

In 1971, however, Wilson did ask Erb for a favor. They had Helio Rise, a colt who ran seventh twice in his races just before the Kentucky Derby. Wilson was dying of cancer. For years, he had been taking a vacation during Derby week and going to Louisville, but never with a horse.

“I owed the man at least that much,” Erb said.

Helio Rise was 58-1 and ran like it. He was beaten by about 20 lengths.

Why, Erb was asked, aren’t more jockeys going into training these days?

“I’ll give you the answer that Eddie Arcaro once gave,” he said. “Toward the end of his riding days, somebody asked Eddie if he would go into training. He told them no. They asked why and he said: ‘Too damn lazy.’ ”

Gary Stevens disagreed, somewhat.

“Jockeys could [become trainers] if they wanted to,” he said. “Out here in California, Danny Velazquez and Frank Olivares, just to name two, have been two fine horsemen. [Bill Shoemaker] was well on his way. Angel [Cordero] was a trainer, in effect, of many horses while he was still riding them. And you can’t tell me that riders like Mike Smith and Jerry Bailey, if they wanted to, couldn’t be successful trainers.”

The stop-and-start arc of Stevens’s career doesn’t preclude a return to training some day. Maybe after he wins his fourth Kentucky Derby, and his ninth and 10th Breeders’ Cup races, he will.

“I loved training,” he said. “There was a kind of serenity when you went to the track with your horses in the mornings. And that one race I won, it gave me a feeling that I had never had before. I was never more satisfied.”

CORRECTION: An earlier version of this story incorrectly stated that Dave Erb was the only Kentucky Derby-winning jockey since 1969 to have a chance to win the Derby as a trainer. In 1993, Bill Shoemaker, who won three Derbies as a jockey, started Diazo in the Derby. Diazo finished fifth.