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He launched a regatta in 1851, then unsuccessfully proposed starting a national subscription for France to send a yacht to the regatta around the Isle of Wight at which, on 22 August 1851, the schooner America won the trophy later renamed the America Cup.
A five-goal player, he won U.S. Open Polo Championship in 1983, the Cowdray Park Gold Cup with the Boca Raton team in 1970, the C.V. Whitney Cup, the Rolex Gold Cup, the America Cup, the Monty Waterbury Cup, the Pacific Coast Open, the 12 and 16 Goal Championships, three Chairman's Cups, the Butler Handicap, the North American Cup and numerous Sunshine League titles.
From 1984-1993, the event was held at Greenwood Raceway and from 1994-2006, the North America Cup was held at Woodbine Entertainment Group's other harness racing venue, Woodbine Racetrack.
He has won the US Handicap, the Sunshine League, the Pacific Coast Open, the Silver Cup, the Monty Waterbury Cup, the America Cup, the US Arena Handicap, and the Interscholastic Arena Championship.