Texas native Bill Boland became a riding sensation at the age of 16 when he won the 1950 Kentucky Derby aboard Middleground while still an apprentice. A day earlier, Boland won the Kentucky Oaks on Ari’s Mona. He also won the Belmont Stakes that year with Middleground and again in 1966 on Amberoid.
July 16, 1933
Texas native Bill Boland became a riding sensation at the age of 16 when he won the 1950 Kentucky Derby aboard Middleground while still an apprentice rider. A day earlier, Boland won the Kentucky Oaks on Ari’s Mona. He also won the Belmont Stakes that year with Middleground and again in 1966 on Amberoid.
Boland was a contract rider for King Ranch and won numerous major races, including the Jockey Club Gold Cup, Whitney Handicap, Massachusetts Handicap (twice), Diana Handicap, Arlington Handicap, Hawthorne Gold Cup (three times), Acorn Stakes, Alabama Stakes, Metropolitan Handicap, San Antonio Handicap, Spinaway Stakes (twice), Dwyer Handicap, Santa Anita Oaks, Man o’ War (twice), Santa Anita Handicap, Suburban Handicap, Wood Memorial, and Woodbine Oaks, among others.
The 1959 recipient of the George Woolf Memorial Jockey Award, Boland rode Beau Purple to three victories over five-time Horse of the Year and Hall of Famer Kelso in 1962 and 1963. Boland also got the best of Hall of Famer Nashua twice, defeating him with High Gun in the Sysonby Stakes and with Midafternoon in the Metropolitan Mile.
Boland, who later spent some time as a trainer, finished his riding career with 2,049 victories and purse earnings of $14,856,095.
Triple Crown Highlights
Won the 1950 Kentucky Derby — Middleground
Won the 1950 Belmont Stakes — Middleground
Won the 1966 Belmont Stakes — Amberoid
Won the Hawthorne Gold Cup — 1952, 1956, 1962
Won the Massachusetts Handicap — 1952, 1956
Won the Man o' War Stakes — 1959, 1962
Won the Kentucky Oaks — 1950