Lost And Found Presented By Horseware: Jockey, Trainer, And Steward Boland Has Left The Track Behind

by | 08.26.2019 | 11:58am
Bill Boland, 2016 Hall of Fame Jockey signing, 2016 Keeneland Spring Meet

After reinventing himself many times, Bill Boland now lives as a typical retiree with golf always on his schedule.

Seven decades before his current incarnation, Boland won the 1950 Kentucky Derby aboard Middleground as a 16-year-old apprentice. That triumph and so many others earned him induction into the Hall of Fame in 2006. Other segments of his life include being a noted trainer, working as a racing official, raising a family, and holding a part time job before focusing fully on a life of leisure.

When not on the links or driving range, Boland said he likely is working on the “honey do” list from Sandy, his wife of 68 years. His chores are minor home repairs and landscaping in their Florida house 25 miles south of St. Augustine. Dining out, entertaining with friends and church activities also are on the agenda.

At age 86, Boland is comfortable in his latest role that no longer includes employment at the golf course as a “cart boy” responsible for tending to the carts and assisting players to the first tee. He is mostly out of touch with Thoroughbred racing except for following the Triple Crown and Breeders' Cup events. His most recent visit to the track was a trip to Churchill Downs for a celebration of Derby winners several years ago.

Thoughts of Boland's 51 years at the track rarely enter his mind.

“When I quit riding, I never missed riding,” he said. “When I quit training, I didn't miss training. When I decided to leave being a racing official in New York, I didn't miss that. I don't even think about it.”

Boland's road to the races began in his native Texas, where his family lived near rodeo grounds. As a child he had his own horse to look after and also tended to the rodeo mounts.

“I would go there every morning to take care of the cowboys' horses—feeding, grooming, whatever,” he said. “I wanted to be a rodeo bull rider. I rode calves, but I never did ride a bull.”

An undated image of Boland in his days as a jockey, shown at Aqueduct

The family moved to Rivera, Texas, about 20 miles from the massive King Ranch famous for producing the finest cattle, American Quarter Horses and Thoroughbreds. His mother met the King Ranch veterinarian who frequented the restaurant at which she worked. She asked him about hiring her sons as riders. Both were hired but Boland's brother became homesick after 10 days and left.

“At the beginning, we broke yearlings without using stirrups,” he said. “I was used to riding bareback so that was no problem. It was a learning experience to [later] ride with short stirrups but I caught on quick.”

When the stable shipped to New York in the spring, Boland went along. He was soon riding races and the victories became routine. He captured the Gallant Fox Handicap aboard Better Self and a week later rode Ari's Mona to victory in the Kentucky Oaks. The next day he won the Kentucky Derby on Middleground.

Boland was presented with the 1959 George Woolf Memorial Award which “honors riders whose careers and personal character earn esteem for the individual and the sport of Thoroughbred horse racing.” He closed his career with more than 2,000 victories after losing interest in being a jockey.

“I got sour on riding but I always wanted to train,” he said. “But I quit too quick. I should have waited a few more years to set myself up better.”

Boland with Steve Cauthen before the 1978 Belmont Stakes

As a trainer, Boland had nearly a two-decade run highlighted by the gray Wise Philip whose 10 victories include the 1978 Gallant Fox Handicap. Based at Belmont Park, Boland left training in 1988 with 100 wins to his credit from a stable that never exceeded 15.

He then took a job for ten years as a New York Racing Association racing official handling various assignments including being a steward.

“That was my favorite part,” he said. “I knew riding and I watched races forever so I knew what was going on. It came easy to me. I was an alternate steward for about eight years.”

Boland said his favorite part of training was the mornings and the best part of competitive riding was the camaraderie.

“I liked the people I was around,” he said. “We were like enemies on the track but when the race was over, we were friends.”

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