Chasing the Triple Crown

Top racehorse trainer Todd Pletcher prepares his million-dollar thoroughbreds for the sport’s ultimate prize.

WORDS Clark Spencer
May / June 2017

Photography MIchele Eve Sandberg

They’re not visible, not in the inky, predawn darkness. But they can be heard, breathing heavily from exertion, their hooves pounding the loamy track in the distinct rhythm of a gallop. There are more than a dozen of the half-ton animals—each with a rider atop its back—going about their morning paces.

One just might be this year’s winner of the Kentucky Derby. “It’s exciting when you’re fortunate enough to have some nice prospects,” says Todd Pletcher, one of the nation’s top thoroughbred trainers. The silver-haired Pletcher is standing on a raised platform overlooking his track in Boynton Beach, Florida, which provides him with a bird’s-eye view of some of the best horse flesh in the world.

And on a balmy morning, some weeks out from the Derby and 1,000 miles from Churchill Downs, he is plotting a course he hopes will bring him victory on the first Saturday in May. Pletcher, who won the 2010 Kentucky Derby with Super Saver, is gunning for another with a powerful arsenal of three-year-olds, all with Triple Crown potential.

Always Dreaming is a frontrunner, having just won the Florida Derby at Gulfstream Park on April 1. Then there’s the gray Tapwrit, winner of the Tampa Bay Derby, and Battalion Runner, a flashy colt who was also making noise at Gulfstream. There’s One Liner, who was taking Arkansas by storm, and Malagacy, a rapidly emerging star. And Pletcher sent Master Plan all the way to the Middle East for the United Arab Emirates Derby, a tune-up for Kentucky, where he emerged in third place.

His is a stable of stars, in some cases million-dollar horses with fashionable bloodlines to match their hefty price tags. It’s no wonder, then, that Pletcher shows up at his barn each morning at 4:30 a.m. to make sure every member of his 180-horse ensemble is feeling 100 percent—taking their temperatures, checking for coughs and making sure they have cleaned their feed tubs.

“He’s a workaholic,” says Pletcher’s father, Jake, a former horse trainer himself. “Besides that he’s got a tremendous memory. He can tell you every horse out there and what’s wrong with them.”

That’s because Pletcher has been around them from an early age. Jake Pletcher says his son—an only child—was riding small ponies when he was six. By the time he was a teenager, he was determined to train horses. Jake told Todd he could do whatever he wanted, just as long as he earned a college degree.

After graduating from the University of Arizona, Pletcher went to work for Hall of Fame trainer D. Wayne Lukas as an assistant. In 1996, the year after Lukas’ Thunder Gulch won the Kentucky Derby, Pletcher went out on his own.

“We started off with seven horses, none of which had ever run a race,” Pletcher says. “We certainly didn’t have any Derby prospects.” Now, Pletcher operates one of the largest and most successful stables in the country.

But a one-man show he is not. Pletcher has 140 employees on his payroll—nearly one for every horse—ranging from grooms and hot walkers to exercise riders, barn foremen, training assistants and office staff.

“There are a lot of moving parts hinging on a lot of people doing their job well,” Pletcher says. Throw in veterinarians, blacksmiths, jockeys and owners and the list of those involved in the success of a racehorse becomes that much larger. Take the owners, who breed and buy the horses, pay the trainers and hope one day to stand in the winner’s circle at the Kentucky Derby with a blanket of red roses draping their horse’s back.

Vincent Viola has dreamed of running a horse for most of his life. He remembers his father taking him to see Secretariat win the Belmont Stakes and sweep the Triple Crown in 1973.

Viola, who owns the Florida Panthers of the National Hockey League and was President Donald Trump’s first choice to serve as Secretary of the Army, says horse racing gives him pleasure in ways that other sports don’t: “It’s almost surreal. It is so much more than just a sport. It’s a state of mind.”

Viola entered the spring with two Pletcher-trained Derby prospects. One was Florida Derby winner Always Dreaming, which he owns in partnership with Anthony Bonomo. The other was Battalion Runner, who also raced in the April 1 Derby, a final stepping-stone to Kentucky.

“It’s almost like waiting for Christmas to come,” Viola says. “Every day, the first thing I think about are those two horses. You always want the time to go quicker.”

But the road to Kentucky is neither paved nor straight. It’s littered with potholes and hurdles, disappointment lurking at every turn. No one understands this better than Pletcher, who has endured his share of heartbreaks over the years.

Pletcher has saddled 45 horses for the Derby, four shy of the record held by Lukas, but only Super Saver managed to land him in the winner’s circle. He’s had horses get sick and fail to make the race. He’s had others knocked out right before the Derby with untimely injuries.

Then there’s the race itself, a demanding 1 1/4-mile test. Because the Derby is the only race in the country that permits 20 starters, traffic congestion is always an issue.

“Something as simple as the wrong post position can really affect your chances,” Pletcher says. “Weather conditions are another element. Rain might cost you. Might help you.”

Super Saver loved the slop. Fortunately for Pletcher, it rained before the 2010 Derby, creating the kind of soupy going the horse found to his liking. But other horses hated wet tracks, and he lost Derbies because of them. “It’s a business in which nothing is ever certain,” he says. “Long shots win. There are just so many elements that you have no control over.”

One variable that can usually be managed is determining which jockey to use. Pletcher has enjoyed much of his success (he’s won more than 4,000 races overall) with standout jockeys John Velazquez and Javier Castellano, though it was Calvin Borel who won the Derby aboard Super Saver.

But even picking out a jockey isn’t always as simple as it seems. Occasionally, top riders have their choice of more than one Derby horse.

“Let’s say Johnny wins the Florida Derby on one horse and the Wood Memorial [another major Derby prep] on another,” Pletcher posits. “Obviously, both owners want Johnny to ride their horse for the Derby. It becomes tough for the owners to accept that he might pick the other horse. So there’s definitely some hand-holding to be done in those situations.” One such event could arise this year.

Castellano, a 39-year-old Venezuelan who has led the nation’s jockeys in earnings each of the past four years, has never won the Kentucky Derby. But he could have his pick of top contenders—Pletcher’s Malagacy and Gunnevera, winner of the Fountain of Youth Stakes at Gulfstream—should both make it to Kentucky. (Gunnevera is trained by Antonio Sano, a fellow Venezuelan.)

Castellano offers high praise for Pletcher, whose horses he has ridden for years. “He’s always thinking of the animals,” he says. “That’s why he’s made it to the next level. Sometimes this game can be very tough. He doesn’t take anything for granted.”

letcher also keeps his owners in mind when mapping out different strategies to get their horses to Kentucky. While he stables nearly all his horses in South Florida during the winter, he tries to keep them from going head-to-head whenever possible. So he sent One Liner to campaign in Arkansas, Tapwrit up to Tampa and Master Plan overseas to the Middle East. “Obviously, it’s in the owners’ best interests to split them all up and never run two against each other,” he says.

If all goes to script and there are no setbacks, the horses will all end up at Churchill Downs. And once Pletcher straps on their saddles and hoists the riders on their backs, his work is finished.

“At that point, it’s out of your hands,” he says. “It’s tense. It’s exciting. It’s what I enjoy.”

Being fortunate enough to win the Derby makes it that much better. Pletcher has won hundreds of important stakes races over the years, some richer than the Derby. He’s received the annual Eclipse Award as the nation’s most outstanding trainer seven times. But there’s one race that gets everyone’s attention, and that’s the Derby.

“When they find out what you do, the first thing anybody who doesn’t know anything about the sport asks is, ‘Have you ever won the Kentucky Derby?’” says Jake Pletcher, Todd’s father. Pletcher has won one. He doesn’t want to stop there.

Only 12 horses in more than a century have pulled off the three-race winning streak. Why is the sport’s ultimate prize so difficult?

Kentucky Derby, May 6

The “Run for the Roses” is America’s only race that permits as many as 20 horses to take part, and getting a “clean trip,” devoid of incidental bumping or sudden roadblocks, is crucial. Then there’s the Derby’s 1 1/4-mile distance. None of the horses have raced farther than 1 1/8 miles, and the extra 1/8 mile is critical.

Preakness Stakes, May 20

The Preakness comes two weeks after the Derby, and top thoroughbreds typically race no more than once a month. Now they’re tackling two tough races in 14 days—and on different surfaces. At 1 3/16 miles, the Preakness is the shortest of the three jewels.

Belmont Stakes, June 10

Often called the “Test of Champions,” the Belmont is the longest of the three, at 1 1/2 miles. Making matters more challenging: While the horse bidding for the Triple Crown is put to the test three times in five weeks, very few of the other top horses race in all three. The Derby/Preakness winner, weary from the compressed schedule, is often taking on fresh horses in the Belmont.


More Business

Zenni's Hindsight Is 20/20

Sights set on Summer

These Businesses Are a Family Affair

This Singapore shop only carries products created through crowdfunding