Jack Fitzsimmons wanted to find a way to both honor his famous grandfather and have a little fun in the Thoroughbred racing game, and maybe even win a few races along the way. Then just like that, the idea of “Sunny Jim” Fitzsimmons Racing was born. Founded in 2012 in honor of the late Hall of Fame trainer James “Sunny Jim” Fitzsimmons, the Saratoga Springs–based racing partnership has been everything Jack hoped it would be.
“Not everyone has a knowledge of what my grandfather accomplished and what he meant to racing, especially as more time continues to pass,” says Jack, one of Sunny Jim’s 17 grandchildren and the managing partner of the syndicate. “The racing partnership was a way to keep his name in the sport. That was the first motivation, and it was important to me. He loved racing so much, and he’s such a big part of its tradition. We’ve been able to introduce some new people to the game, and all the experiences so far have been very positive for us.”
Born in New York City in 1874, Sunny Jim was one of the most accomplished and beloved trainers in American history. After spending about a decade as a jockey, he went on to win a documented 2,275 races as a trainer, including 13 Triple Crown races (a record since surpassed by D. Wayne Lukas and Bob Baffert). The popular trainer was also the first to train two Triple Crown winners, sweeping the Kentucky Derby, Preakness Stakes and Belmont Stakes with Gallant Fox in 1930 and Omaha in 1935 (only Baffert has since won the Triple Crown twice). At Saratoga Race Course, Sunny Jim set records for the most wins in both the Saratoga Cup (10) and Alabama Stakes (eight) and won just about every other major race at the Spa, including two editions of the Travers.
In 1958, Sunny Jim was inducted into the Hall of Fame. Still ranking among the elite trainers in the Sport of Kings when he retired in 1963, he served as grand marshal for the centennial celebration parade of Saratoga racing’s founding that summer. He died three years later at the age of 91.
“Summer in Saratoga has always been a big tradition for the family,” says Jack. “We’ve always had about 10 houses on Lake Desolation near Saratoga with all the aunts and uncles and everybody coming together there for big gatherings every year, and of course, we love being at the track.”
The racing partnership was a natural extension of those family traditions. Jack worked at Saratoga Race Course during the summers of his college years while attending the University of Notre Dame. He drove tractors between races, painted fences and barns, and learned other aspects of the sport along the way. Later, while stationed at Fort Lewis near Seattle during his time in the Army, Jack also worked as a clerk at Longacres Racetrack. When he attended law school, he doubled as a security guard at Maryland tracks Bowie, Pimlico and Laurel. And although he went on to spend 28 years as an attorney for State Farm, Jack also held a trainer’s license, winning races in Maryland, as well as Delaware Park, Atlantic City, Penn National and Charlestown, among others.
“When I was in the Army, I’d be done by about three in the afternoon, and then I’d sell tickets at the track at night,” he says. “When I worked for State Farm, I was fortunate to be able to set my own time and work with the horses in the morning and have them in races at night and on weekends. It was demanding, but I’ve always been in racing and loved it. It’s in the blood.”
“Sunny Jim” Fitzsimmons Racing’s most successful horse to date has been New York–bred Hannah’s Smile, who won or placed in 10 of 14 starts and earned $227,795 before being retired last year. She is now in foal to New York stallion War Dancer. At press time, one of the partnership’s horses, Win With Pride, had nabbed a win and place at Belmont already, and Jack was hoping to have partnerships together for Saratoga as well.
“We’re always interested in welcoming new people to racing ownership,” says Jack. “We make it fun and affordable. My grandfather loved what he did, and he always had a smile for everyone. It didn’t matter if you were some millionaire horse owner or a stable groom. He loved people and the atmosphere of racing. That’s really at the heart of what we do. I think he would have been proud of ‘Sunny Jim’ Racing.”