Two-Sport Superstars: The Thoroughbreds That Find Success After Their Flat-Track Careers End

When was the last time a baseball star won a World Series, retired and then went on to become a superstar in, say, football? That just doesn’t happen—for humans, that is. For retired racehorses—or off-track Thoroughbreds (OTTBs), as they’re known—galloping off the track and into a successful second career is fairly commonplace. Take Icabad Crane, for example, whom I’ve had my eye on for the majority of his career. As a flat-track competitor, he ran a close third behind winner Big Brown in the 2008 Preakness Stakes and took the Evan Shipman at Saratoga Race Course in 2011. All told, in 33 starts, Icabad Crane earned a respectable $585,980. He was retired from racing at eight years old, but didn’t skip a beat, starting to retrain in the equestrian category of eventing—basically, the sport’s triathlon, where a rider and his or her horse compete in a trio of disciplines: dressage, stadium jumping and cross-country.

Of course, a skilled competitor such as Icabad Crane needed an equally adept human rider and trainer to team up with. That turned out to be two-time gold medal-winning Olympian Phillip Dutton, whom I had the chance to interview a few years ago. In 2014, Dutton was retraining Icabad Crane with the goal of entering him in an annual competition known as the Thoroughbred Makeover, which involves a rider and horse taking part in two of ten disciplines ranging from barrel racing to polo, dressage and jumping. Judges score each team’s performance per category and then, just like on American Idol, the audience gets to vote on and determine which horse earns the title of America’s Most Wanted Thoroughbred. That year, the honor went to Icabad Crane. And while it doesn’t hurt to be a gold medal-winning Olympian, any qualified rider—professional trainer, talented junior or amateur—can enter an OTTB in the Thoroughbred Makeover. The horse just can’t exceed ten months of retraining. Did I mention that each team competes for a portion of a $100,000 prize purse?

This year’s Thoroughbred Makeover, which takes place October 2-5 at the Kentucky Horse Park in Lexington, is already shaping up to be a competitive one. And I’ve been scrolling through hundreds of entries, trying to decide which riders to root for. My money’s on one of 29 New Yorkers competing this year, Sarah Hepler, a professional dressage trainer who hails from Trumansburg, NY (near Ithaca). Hepler’s story is an inspiring one, to say the least: After losing an arm in a car accident when she was ten and being turned away from the barn where she had been taking riding lessons, she found a new stable that encouraged her to chase her dreams. Since then, she’s found her niche transforming OTTBs into dressage horses. Last year, Hepler finished third in the Thoroughbred Makeover riding Flat Leaver, who made 38 starts as a racehorse, including 8 wins, and had earnings of $118,980. This year, she’ll be partnering with Jacapo, who won 6 out of 53 career starts to the tune of $138,625.

Of all the disciplines at this year’s Thoroughbred Makeover, I’ll be most closely watching the ranch work category…for selfish reasons. I’m hoping to pick up some hot training tips I can use with my own mare. But I’ll also be cheering for Hepler and the hundreds of other riders who’ve helped retrain thousands of retired racehorses throughout the years.

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