In 2000, Kenny Troutt and Bill Casner, founders of Excel Communications, a long-distance telephone service and communications company, founded WinStar Farm after buying the 1,450-acre Prestonwood Farm property near Versailles, Ky., from brothers Art, Jack and J.R. Preston. In 2010, Troutt bought out Casner’s portion of WinStar, and is now the sole owner. With the Race Track Chaplaincy of America, Troutt created the White Horse Award, presented annually to a farm or racetrack worker who performs an unselfish heroic act.
WinStar has focused on developing a leading breeding program and stands leading sire Distorted Humor, among others. It first gained national fame as the breeder of 2003 Kentucky Derby and Preakness Stakes winner Funny Cide, a son of Distorted Humor.
In 2008 WinStar won the Grade 1 Goodwood Stakes with Well Armed, who went on to win the Dubai World Cup in 2009. The following year the farm won the Kentucky Derby with Super Saver while Drosselmeyer won the 2010 Belmont Stakes. After the 2010 season, WinStar received its first Eclipse Award for outstanding owner. In 2011, Drosselmeyer won the Breeders’ Cup Classic.
WinStar claimed a third-place finish in the 2013 Kentucky Derby with Revolutionary, who also won both the Louisiana Derby (Grade 2) and Withers Stakes (Grade 3). In 2015 WinStar partnered with Stonestreet Stables to campaign Carpe Diem to a win in the Blue Grass Stakes at Keeneland. With a record of four wins and a second from five starts in his career, Carpe Diem went off as the third choice in the Kentucky Derby, but finished unplaced.
In 2016, WinStar won the Arkansas Derby with Creator, who subsequently was unplaced in the Kentucky Derby after enduring a troubled trip. He rebounded in a big way, however, in the Belmont Stakes when he rallied powerfully to nip Destin for the win in the closing strides.
After the 2016 season, WinStar Farm was named the Eclipse Award winner as Outstanding Breeder, and it received another Eclipse Award in the same category in 2020 when it had a stellar year with 3-year-old fillies, breeding Preakness Stakes winner Swiss Skydiver and Longines Kentucky Oaks winner Shedaresthedevil.
WinStar owned 2018 Triple Crown winner Justify in partnership with China Horse Club, Head of Plains Partners, and Starlight Racing.