Thoroughbred Horse Racing
William Whitney was also a major investor in thoroughbred horse racing, hiring the best trainers, buying the best horses, and engaging the services of the best jockey of the day. He established Westbury Stable with a string of Thoroughbred race horses, competing against the successful stable of business associate, James R. Keene. At his vast summer estate near Old Westbury on Long Island, Whitney built an 800-foot (240 m) stable with 84 box stalls and an adjoining mile-long training track. Around the start of the 20th century, in the United States his horses were trained by future U.S. Racing Hall of Fame inductee John W. Rogers and in England by John Huggins.
Whitney maintained a city residence in New York, a Venetian palace and 5,000 acres in Wheatley Hills, near Jamaica, L.I.; a Sheepshead Bay house, with a private track covering 300 acres; a mansion with 700 acres at Lenox, MA; October Mountain summer cottage, 10,000 acre estate including 800 acre fenced-in game reserve, in Washington, MA; Stony Ford Farm, New York, used as an auxiliary to his Kentucky Stock Farm; an Adirondack game preserve of 16,000 acres; a lodge at Blue Mountain Lake with a fine golf course, a Blue Grass farm of 3,000 acres in Kentucky. Whitney also spent time in the equestrian community of Aiken, South Carolina revamping a local cottage into a winter residence with 69-rooms, 15 bathrooms, a full-size ballroom, a squash court and a stable to house 30 horses. His involvement in Aiken along with that of Thomas Hitchcock, the Vanderbilt family, the Astor family and other equestrian minded business associates helped establish the premier Aiken Winter Colony. Aiken remains a haven where horses are brought in from the north to train and enjoy a more temperate winter.
He was the breeder of twenty-six American stakes winners, including the great filly Artful from his stallion Hamburg. On June 5, 1901, Whitney won England's Derby with Volodyovski, leased by him from Lady Valerie Meux. On October 24, 1903, the New York Times reported that W. C. Whitney had entered into a ten-year lease deal with A. J. Alexander for one thousand acres (4 km²) of the Wood Stud farm property at Spring Station, Kentucky.
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