WinStar Farm is an American Thoroughbred horse breeding and racing farm near Versailles, Kentucky. Formerly known as Prestonwood Farm, it was owned by Houston, Texas oilmen Jack, Art, and J. R. Preston whose better known horses included Da Hoss and Victory Gallop.
In 2000, Kenny Troutt and Bill Casner, both with long-standing interests in horses came together to purchase Prestonwood, adding to its area, and renaming it WinStar Farm. Included in the purchase were the stallions Kris S. and Distorted Humor. Kris S. died in 2002 at the age of 25 after siring five Breeder's Cup winners and three Eclipse Award winners whose combined career earnings were in excess of $50,000,000. He is buried at WinStar, just outside the entrance to the stallion barn.
Trainer W. Elliott Walden is vice president of racing and bloodstock services for WinStar Farm.
Distorted Humor stands across the aisle in the WinStar stallion barn from the 2000 Horse of the Year, the 2005 leading freshman sire and the two-time Breeders' Cup Classic winner (2000 and 2001), Tiznow. Next to Tiznow is the winner of the 2004 Breeder's Cup Sprint, Speightstown. Down the row is the 1998 Belmont Stakes winner and the 1999 U.S. Champion Older Male Horse, Victory Gallop. Joining them in 2006 was the homebred Bluegrass Cat, winner of the Remsen Stakes as a two-year-old and the Haskell Invitational Handicap at three. In 2007, Distorted Humor's son, Sharp Humor came to stand at WinStar. Five of Distorted Humor's sons: Flower Alley, Da Stoops, It's No Joke, Comedy Show and Sharp Humor will stand their first year for the 2007 breeding season. Well Armed, a WinStar Farm owned horse, won the 2009 Dubai World Cup by a record 14 lengths.
In 2010 WinStar got their first Derby win with Super Saver.