- April 26, 2024
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Days after he made a hole-in-one at Palm Harbor Golf Club, Bill Boland missed another on the same hole by about 10 inches.
Boland knows what it’s like to win and then come up just short. The 90-year-old Boland is a Hall-of-Fame jockey who won the Kentucky Derby in 1950 at age 16 and almost won the Triple Crown that year aboard the colt Middleground.
He is the youngest jockey to win a Kentucky Derby since 1900. An apprentice rider at the time, Boland also won the Belmont Stakes. But he finished second in the Preakness Stakes, the Triple Crown’s middle race, to fellow Hall-of-Famer Eddie Arcaro riding Hill Prince.
“It was bad luck,” Boland recalled of the Preakness race — a memory he’s been asked to replay over and over during the past 73 years. “A horse took me to the outside fence, and the winner got through to the inside. He opened up a five-length lead.”
Middleground got within a couple of lengths of Hill Prince, but the early bump to the outside took too much out of him, Boland said, and Hill Prince wound up winning by five lengths.
Boland retired from riding in 1969, trained horses for another 19 years and then became a racing official for 10 years. He and his wife, Sandy, retired to Palm Coast in 1998. He’s been golfing “on and off” for 40 years, he said.
When asked what his handicap is, he quipped, “playing golf.”
He plays in a Monday morning group and a Friday morning group at Palm Harbor. On Monday, July 24, Boland shot a hole-in-one on the par-3 No. 17 hole. Playing from the gold tee (153 yards), he aced the hole, using a 5-utility club.
Boland nearly repeated the feat on Friday, July 28, barely missing. That would have been the third hole-in-one in his lifetime. He said he also had an ace at Cypress Knoll about 10 years ago on the old No. 18.
She was dancing around. She was excited that this little kid won.” — SANDY BOLAND on her mother's reaction listening to the 1950 Kentucky Derby on the radio.
In addition to playing golf, Boland helps raise money for the Permanently Disabled Jockeys Fund. He and Sandy recently returned from Las Vegas, where he and 13 other Hall-of-Fame jockeys, along with seven paraplegic former jockeys, signed autographs, raising $450,000 for the fund in one day.
The Bolands have been married for 72 years. Sandy was not a horse racing fan, but her parents loved the racetrack, she said. Her mother listened to the 1950 Kentucky Derby on the radio and rooted for Boland to win the race.
“She was dancing around. She was excited that this little kid won,” Sandy said.
Sandy lived on Long Island, New York, and her parents took her to the Belmont Stakes that year.
“I took a picture of him and Eddie Arcaro, not knowing either one of them,” she said.
Shortly after that, she was bowling with friends one day, and there he was.
“He offered to take me home,” she said. “Then he was over every night. He loved my mother’s cooking.”
They were married in 1951. She was 19, and he had just turned 18.
“My husband is wonderful. He’s been kind, successful, he’s just great,” Sandy said.
Boland shot 80 on the day of his hole-in-one at Palm Harbor, he said. His racing career is long behind him, but he is as competitive as ever on the golf course.
“I’m still young,” he said.
