SARATOGA LIVINGThe City. The Culture. The Life.

The first time I met Jimmy Wilsey was in the fall of 2017. A talented, well-respected Thoroughbred exercise rider and jockey, Jimmy had last competed at Saratoga Race Course seven years prior. I remember it being a particularly cold morning—and it wasn’t at a place you’d expect to meet a talented sportsman: We were at Code Blue Saratoga, the city’s homeless shelter, where he was staying as a guest. That morning, I was there as a volunteer, serving breakfast, and I couldn’t help but wonder how a professional jockey could end up in a homeless shelter in Saratoga, a city globally famous for horse racing. 

This past spring I reached back out to Jimmy, and he was kind enough to share his story with me—and by extension, you. 

It turns out that he’d grown up in Saratoga and been fully entrenched in the horse racing community since he was a little boy. His father, Dan, had been a successful harness jockey in the 1970s and ’80s and had taught his son, from an early age, the hard-scrabble life that comes with being part of the horse racing community. Jimmy had to be up at the crack of dawn to do barn chores, such as feeding and watering horses—even in the dead of winter in zero-degree weather. It was tough work—and it made every other job on the planet seem easy to Jimmy.

By the age of ten, Jimmy had made up his mind that he wasn’t going to follow in his father’s footsteps in the harness world, but rather, set his sights on racing Thoroughbreds. Thankfully, his father embraced his son’s dream, and through his father’s connections, Jimmy started riding Thoroughbreds almost immediately. By ninth grade, he was riding so well that high school became an afterthought—and he asked his father if he could drop out to pursue his jockey’s license, so that he could ride full time. Naturally, his father had some reservations about the idea, but following a heavy discussion, he agreed and signed his son’s paperwork. Jimmy was now on the path to greatness.

For the next three decades, Jimmy worked as a freelance exercise rider and licensed jockey, gigging for many of the top trainers in the industry, including Todd Pletcher and Gary Contessa. In addition to racing at Saratoga, Jimmy picked up mounts at Belmont Park, Finger Lakes Racetrack and Aqueduct Racetrack, among others. What kept him coming back for more? I asked him. “It’s the excitement of getting on a horse and taking it into the gate while it’s rearing up,” he said. He had a special place in his heart for his home turf at Saratoga Race Course, even though he never won a race there. Jimmy’s career was going gangbusters throughout the ’90s and first decade of the aughts. He’d come a long way from those days of doing barn chores in the bitter cold; he was now spending his winters in Ocala, FL, returning to Saratoga every summer for the big racing meet.  

In the summer of 2017, just a few months before I first met him, Jimmy was renting a motel room in town in advance of the Saratoga meet, unsure of when he’d need to return to Florida. That July, he was dealt a bad hand: Just before the beginning of the meet, he was badly burned on his leg while helping fix a friend’s car. It was so bad that it prevented Jimmy from riding. “I was like a fish out of water,” he said. Though his finances began to dwindle because of his mounting medical bills and that motel room, Jimmy kept a positive outlook, hopeful that he’d be able to ride before the end of the meet. He was healing quickly, and just as the meet began winding down, Jimmy was riding again. Phew.

But about three weeks later, catastrophe hit again, and this time, it was a devastating blow. While crossing the road in Wilton, Jimmy was hit by a car, and the injuries he sustained were so severe that he was, once again, unable to ride. This time, he spiraled into depression. With his livelihood and earnings on hold—not to mention a whole new pile of medical bills to pay—it wasn’t long before Jimmy couldn’t afford his motel room. Despite having a loving family and deep contact list in the industry, Jimmy chose not to ask for help. So, for the first time in his life, he became homeless, slipping deeper into depression and starting to drink heavily. “I hit rock bottom,” he told me. When it got too cold outside to bear, he decided to enter Code Blue. Although he remembered the staff being wonderful, he found himself having a bit of an out-of-body experience there: He looked at other guests and thought, “I don’t belong here.” And after some much-needed self-reflection, Jimmy knew that he had to stop drinking to get his life back together. He worked hard on his sobriety and recalled that the staff at Code Blue had been incredibly supportive, celebrating each sober day with him. He was 54 days dry when he was finally able to leave Code Blue, this time, with a job and a place to stay. As soon as he saved up enough money, he took the bus back down to Florida and never looked back. 

These days, Jimmy lives near his mother in Florida and has continued to maintain his sobriety. He’s gotten himself back into “jockey shape,” as he describes it, working as an exercise rider and doing what he’s always known and loved. When I asked Jimmy if he planned to race again, he said, hesitantly, “I’ve been thinking about it.” At the end of the day, Jimmy told me that he doesn’t let the brief time he spent at Code Blue define him; it was just one in a series of “stepping stones” that helped him get his life back together. “Code Blue asked me no questions,” he said. “They just gave me what I needed to get through the worst time in my life.” I came away from our conversation inspired—and I hope that someday, maybe, we’ll get to see Jimmy Wilsey race again at Saratoga.    

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.

saratoga living has a thing about attempting to predict the future. Well, at least when it comes to horse races. You might remember that we chose Good Magic to take home the 2018 Kentucky Derby. Well, look, he came in a close second, which means that had you boxed your exacta with Justify, you would’ve been a winner. And then we tried to predict the results of the 2019 Kentucky Derby. No dice there, but the show-winner, Tacitus, is our experts’ pick for the coveted Midsummer Derby at Saratoga Race Course. Check out our expert panel’s advice below.

Maximum Security

“Simply the best three-year-old out there! I bet him on Kentucky Derby Day—but had my winning trifecta stripped because of the disqualification. If he goes in the Travers, look for him to win by at least five lengths.” –Joe “Woody” Wood, Master Barber at Woody’s Barbershop and amateur handicapper

Tacitus

“I’ll put my money on Tacitus from the Bill Mott barn. He ran a solid fourth in the Derby (elevated to third via the DQ) and would’ve likely won the Belmont Stakes given a better trip.” –Brien Bouyea, saratoga living Sports Editor and Communications Director at the National Museum of Racing and Hall of Fame

Tacitus

“I’ll select Tacitus, who performed well in the Triple Crown events for trainer Bill Mott. He’s in good hands with Bill and always seems to deliver a solid race. It just might be Tacitus’ turn on Travers Day.” –Michael Veitch, Saratoga horse racing historian and author (and co-author, with Bouyea, of The Travers: 150 Years of Saratoga’s Greatest Race)

Tacitus

“Tacitus had a less-than-ideal trip in the Kentucky Derby, when he was forced wide before coming with a good late run, and he couldn’t have been any wider in the Belmont Stakes while Sir Winston rode the advantageous inside lane. The well-bred Tacitus is definitely due a good trip or two, and he just might get one in the Travers Stakes this summer at Saratoga.” –Dan Illman, Executive Producer/Host, DRFTV

saratoga living asked five incredible female professionals in the horse racing industry how they feel about working in a predominantly male sport, and how it’s impacted their career. Here’s what they said.

Kathryn Sharp

Claim To Fame: Co-founder and director of marketing and strategic partnerships for horse racing’s first industry-wide convention and festival, Equestricon, and owner and breeder via AJ Suited Racing Stable.

Quote: “When our team was filling out our speaker roster for Equestricon, we were disappointed at how difficult it was to recruit enough women in executive roles who could represent major industry organizations. There are a number of incredible women in these posts, but not as many as I’d like to see. While this discrepancy isn’t unique to horse racing, and we can and should do better, I’m encouraged by the many remarkable women shaping the future of the sport every day.”

Abigail Adsit

Claim To Fame: Thoroughbred trainer with more than 728 career starts, 90 wins, 77 places, 114 shows and $3,336,772 in earnings.

Quote: “Being a woman in this male-dominated sport has made me stronger as an individual. There have been many times that I’ve shaken my head at the fact that as a woman, I’ve had to jump through ten more hoops than my male colleagues. Over the years, I’ve learned that being a female in a predominantly male sport has required intelligence, integrity and expertise in my training, along with a good bit of humor.”

Alicia Hughes

Claim To Fame: Director of communications at the National Thoroughbred Racing Association (NTRA), who spent more than two decades as a horse racing journalist.

Quote: “On the whole, my career has been a very positive experience, as I feel my knowledge and work ethic has been recognized and respected by the majority of my peers. While there will always be those who think they can get away with belittling and/or objectifying women, I’m proud to work alongside many men who are suitably horrified by such behavior and many female colleagues who respond to such adversity by fighting back with their words and their ability.”

Nicole Russo

Claim To Fame: Journalist at The Daily Racing Form, with a decade of experience in horse racing journalism.

Quote: “I’ve been very lucky to have come behind some trailblazing women in general sports writing, who paved the way for women to be given fair access, even though those issues definitely still rear their heads, and to have also come behind some women who knocked down walls in turf writing, including Jennie Rees. I’m now conscious of trying to be a role model for upcoming female sports writers, and I hope to always show them that you can bring your authentic self to work.”

Penelope Miller

Claim To Fame: Senior manager of digital media for The Jockey Club’s digital platform, America’s Best Racing, who’s worked on breeding farms in Florida, Kentucky and Australia, as well as at Tampa Bay Downs.

Quote: “I think women still have a long way to go until they’re occupying the same amount of space as men in this sport; we’re still outnumbered in press boxes, shed rows and board rooms. However, I see more women working as professionals in the sport of racing as the years go by, and I hope these women will serve as role models to young women who want to make their careers in the Thoroughbred industry.”

I would’ve loved to have been a railbird at the 1930 Travers Stakes at Saratoga Race Course. Sure, it would’ve been a dream come true to see legends such as Man o’ War, Whirlaway and Native Dancer in the flesh, but in terms of Saratoga racing lore, nothing would’ve compared to witnessing the remarkable and unexpected feat Jim Dandy pulled off on that August afternoon some nine decades ago. This one was a whopper.

That year’s Travers saw a sea of racing fans at Saratoga Race Course. The New York Herald-Tribune reported a record crowd of 50,000, although other sources were more conservative. They came from far and wide to see Triple Crown winner Gallant Fox take on Whichone, whom he’d beaten in that year’s Belmont Stakes. A product of William Woodward’s Belair Stud, Gallant Fox was favored at 1-2 odds, with Whichone at 7-5. The two others in the field were afterthoughts. Sun Falcon was dismissed at odds of 40-1, while Jim Dandy was considered hopeless at 100-1. There was national radio coverage, one of the earliest live broadcasts of a horse race, and New York Governor (and future US President) Franklin D. Roosevelt was in the crowd, as well as retired heavyweight boxing champion Gene Tunney.

Heavy rain the night before turned the track into a quagmire. The rain continued into Travers morning and more showers followed in the afternoon. To help accommodate the massive crowd, Saratoga Race Course’s infield, which hadn’t been accessible to the general public for years, was opened following the running of the Beverwyck Steeplechase.

At the outset of the featured race, all the horses broke well, with Gallant Fox taking an early lead on the outside. Whichone stayed close and provided constant pressure. The race soon became the showdown everyone anticipated, as Gallant Fox and Whichone battled on the front end with the longshots falling well behind. Gallant Fox led at the mile marker, but the deep mud was taking its toll. Turning for home, Whichone forced the exhausted Triple Crown winner wide. The timing was right for Jim Dandy to move on the leaders. With the favorites struggling, the horse seized the opportunity with an all-out charge along the rail. While Gallant Fox and Whichone appeared anchored in the mud, Jim Dandy skipped through the slop and began to draw off in astonishing fashion for an eight-length victory. “The cheering died,” reported The New York Times. “Then it resumed, for no one believed Jim Dandy could stay in front. But Jim Dandy kept going farther and farther away and won in a gallop, with jockey Frank Baker looking back to see what was happening.”

All these years later, it’s impossible to make sense of the results. Jim Dandy was winless in ten starts the year prior to the Travers. He finished a dismal eighth of nine in a minor race at Saratoga only eight days earlier, and his seasonal earnings at the time amounted to just $125.

But perhaps Jim Dandy shouldn’t have been completely dismissed, considering the conditions. The prior year, he won the Grand Union Hotel Stakes at Saratoga at odds of 50-1. The track that day featured similar conditions to his Travers victory. He was said to have “eggshell hooves,” which bothered him on fast tracks. The soggy mud, however, seemed to have acted as a restorative elixir for this greatest of longshots.

Jim Dandy raced until the age of 12. He was retired in 1939 after 141 starts. He won only seven of them and finished last in more than half of them. In 1964, the New York Racing Association introduced the Jim Dandy Stakes to pay homage to the mud-loving miracle Travers winner. A little piece of advice: never count out the longshots. I sure don’t.