WinStar Farm
An American Thoroughbred breeding, racing, training, and stallion operation based near Versailles, Kentucky.
Last updated August 24, 2026
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Overview
WinStar Farm is an American Thoroughbred horse farm and racing operation located near Versailles, Kentucky. Its activities combine commercial stallion standing, broodmare ownership, horse breeding, young-horse development, racing partnerships, sales participation, and related breeding-rights transactions. The farm is owned by entrepreneur Kenny Troutt, who established WinStar with Bill Casner in 2000 after the partners acquired Prestonwood Farm and renamed it. The property has deep agricultural and local historical roots. Much of the modern farm developed from Silver Pool Farm, land settled by the Williams family in the late eighteenth century, and later from Prestonwood Farm, an operation associated with notable racehorses including Da Hoss and Victory Gallop. Historic structures on the property include an early farmhouse, a smokehouse, a converted tobacco barn, and a stone-lined spring-fed pond. Parts of the property lie within the Pisgah Rural Historic District and are recognized for their architectural and landscape significance. WinStar's commercial identity has been built particularly around its stallion program. The farm inherited Distorted Humor in the Prestonwood transaction and acquired Tiznow in 2002. Tiznow, the only two-time winner of the Breeders' Cup Classic, became a highly successful sire and helped establish WinStar as a significant national breeding brand. Other stallions associated with the farm have included Kris S., Victory Gallop, Speightstown, More Than Ready, Congrats, Pioneerof the Nile, Super Saver, and Tiznow. Pioneerof the Nile's importance was amplified by his role as the sire of American Pharoah, the 2015 American Triple Crown winner. The farm also operates as an owner and breeder of racehorses. Its horses have won major American races including the Kentucky Derby, Belmont Stakes, Breeders' Cup Classic, Breeders' Cup Mile, Haskell Invitational, Santa Anita Derby, and Dubai World Cup. Notable horses connected with WinStar include homebreds Bluegrass Cat, Colonel John, Well Armed, Super Saver, Drosselmeyer, and Tourist, as well as Creator, acquired as a yearling. WinStar was named Outstanding Owner at the 2010 Eclipse Awards and Outstanding Breeder at the 2016 Eclipse Awards. The farm's most internationally visible racing achievement came with Justify. A WinStar-led partnership purchased the colt as a yearling and placed him in training with Bob Baffert. Justify won the 2018 Kentucky Derby, Preakness Stakes, and Belmont Stakes, becoming the thirteenth American Triple Crown winner and the first since 1882 to win the Kentucky Derby without racing at age two. Following his retirement, the partnership sold his breeding rights to Coolmore's Ashford Stud, illustrating how elite racing success can be converted into long-term stallion value. WinStar has expanded from its original property through additional land acquisitions and developed substantial stallion, broodmare, quarantine, and young-horse facilities. A new stallion barn completed in 2013 provided housing for up to 18 stallions, access to breeding sheds, viewing areas, and turnout paddocks. Its training operation has prepared young Thoroughbreds for racing, with graduates including Songbird and Honor Code. The farm also promotes breeding-access programs such as Dream Big, which has offered breeders a path toward lifetime breeding rights based on producing qualifying live foals. WinStar's current positioning is that of an integrated, high-profile Thoroughbred enterprise rather than a simple boarding farm: it links bloodstock acquisition, breeding, racing performance, sales strategy, and international stallion distribution.
History
The land associated with WinStar Farm has an agricultural history extending to the settlement period of central Kentucky. The original Silver Pool Farm was established by the Williams family after the area was surveyed in 1788. The Williams property supported livestock raising and hemp-related manufacturing and remained in the family for more than a century. Its historic landscape includes an early farmhouse dating from approximately the 1780s or 1790s, a brick smokehouse, a tobacco barn later adapted for horses, and a spring-fed stone-lined pond. These features are connected with the Pisgah Rural Historic District and remain part of the property's heritage. Most of the relevant acreage later became Prestonwood Farm, owned by Houston-based members of the Preston family. Prestonwood developed a notable Thoroughbred operation and was associated with horses such as Da Hoss and Victory Gallop. In 2000, Kenny Troutt and Bill Casner acquired Prestonwood. The new owners renamed the property WinStar Farm, establishing the modern enterprise and retaining important bloodstock, including Distorted Humor and Kris S. WinStar's early expansion centered on the purchase and development of high-value stallions. In 2002, the farm acquired Tiznow, winner of the Breeders' Cup Classic in 2000 and 2001. The acquisition was considered a calculated investment because Tiznow's pedigree was not then viewed as fashionable by every segment of the market. His subsequent performance as a sire validated the strategy: he became a leading freshman sire in 2005 and remained among North America's notable sires for many years. Distorted Humor, already part of the Prestonwood assets, also became a major pillar of the program and sired important winners including Funny Cide and Drosselmeyer. Doug Cauthen became WinStar's first president and chief executive. In 2005, W. Elliott Walden joined the management team as vice president and racing manager after training Distorted Humor and other WinStar horses. When Troutt and Casner ended their partnership in 2010, Troutt became WinStar's sole owner. Walden succeeded Cauthen as president and chief executive later that year. The racing operation grew alongside the breeding business. WinStar-owned or bred horses won major races across the United States and abroad, including the Dubai World Cup, Kentucky Derby, Belmont Stakes, Breeders' Cup Classic, Breeders' Cup Mile, Santa Anita Derby, and Haskell Invitational. Super Saver won the 2010 Kentucky Derby, Drosselmeyer won the 2010 Belmont Stakes and 2011 Breeders' Cup Classic, Creator won the 2016 Belmont Stakes, and Tourist won the 2016 Breeders' Cup Mile. These results contributed to WinStar's 2010 Eclipse Award for Outstanding Owner and its 2016 Eclipse Award for Outstanding Breeder. Facilities were expanded as the farm grew. By the mid-2010s, the property covered more than 2,400 acres and supported a sizable stallion roster, broodmare band, and groups of weanlings and yearlings. A new stallion barn completed in 2013 was designed for 18 stallions and connected to two breeding sheds and viewing spaces. Additional paddocks, quarantine accommodation for stallions traveling to the Southern Hemisphere, and a young-horse training complex broadened the farm's operating capabilities. The training program has introduced young Thoroughbreds to basic racing skills, with graduates including Songbird and Honor Code. The defining event in WinStar's public history was Justify's 2018 Triple Crown. A WinStar-led partnership purchased Justify for $500,000 at the 2016 Keeneland September yearling sale. Trained by Bob Baffert, Justify began racing at three and won the Kentucky Derby, ending a long-standing drought associated with horses that had not raced at two. He followed with victories in the Preakness Stakes and Belmont Stakes, becoming the thirteenth American Triple Crown winner. His breeding rights were subsequently transferred to Coolmore's Ashford Stud, demonstrating the commercial importance of elite race performance. WinStar continues to combine breeding, stallion management, racing ownership, sales activity, and horse development. Its programs are designed both for large commercial breeders and for partners seeking access to high-quality bloodstock. The farm's identity rests on the integration of historic Kentucky land, modern breeding infrastructure, elite stallions, and a record of success in the sport's most prominent races.
- 2018
Justify wins the Triple Crown
[1]Justify won the Kentucky Derby, Preakness Stakes, and Belmont Stakes for a WinStar-led ownership partnership.
- 2016
Outstanding Breeder Eclipse Award
[1]WinStar received the Eclipse Award for Outstanding Breeder after a leading North American season.
- 2013
New stallion barn completed
[1]WinStar expanded its breeding infrastructure with a purpose-built stallion facility.
- 2010
Ownership partnership ends
[1]Bill Casner and Kenny Troutt dissolved their partnership, leaving Troutt as WinStar's sole owner.
- 2010
Outstanding Owner Eclipse Award
[1]WinStar was recognized as the Eclipse Award's Outstanding Owner.
- 2002
Tiznow joins the stallion program
[1]WinStar acquired Tiznow, the two-time Breeders' Cup Classic winner who became a leading sire.
- 2000
Prestonwood Farm acquired and renamed WinStar Farm
[1]Kenny Troutt and Bill Casner purchased Prestonwood Farm and created the modern WinStar Farm operation.
- 1788
Silver Pool land surveyed
[1]The area later incorporated into WinStar Farm was surveyed during the settlement of central Kentucky.
Products and positioning
A vertically integrated American Thoroughbred breeding and racing enterprise focused on elite bloodstock, stallion quality, racehorse ownership, and long-term breeding value.
Equine breeding · 2000
Stallion breeding services
WinStar's stallion division offers access to Thoroughbred sires standing at the farm. The program supports commercial breeders through mating decisions, breeding arrangements, stallion management, and promotion of bloodlines with proven racing or sire performance. Its historic roster has included influential stallions such as Distorted Humor and Tiznow, as well as sires connected with major American racing achievements.
Horse racing · 2000
Thoroughbred racehorses
WinStar owns, breeds, acquires, and campaigns Thoroughbred racehorses through direct ownership and partnerships. Its racing portfolio has included classic winners and champions such as Super Saver, Drosselmeyer, Creator, Tourist, and Justify. The operation uses racing results to establish the value of its bloodstock and to support future breeding careers.
Horse training
Young-horse development
The farm maintains facilities for the preparation of young Thoroughbreds, including weanlings and yearlings. Its training operation introduces horses to foundational racing skills before they proceed to more advanced preparation or sale. Horses associated with this program have included Songbird and Honor Code.
Breeding partnership
Dream Big breeding program
Dream Big is an access-oriented breeding initiative described as giving participating breeders the opportunity to earn a lifetime breeding right to a young stallion after producing two live foals from the stallion's initial books. The program reflects WinStar's effort to broaden participation in its stallion business while building demand for emerging sires.
Marketing campaigns
- Dream Big
United States
WinStar promoted Dream Big as a breeder-participation program linked to the early books of a young stallion. Its structure allowed qualifying breeders to pursue a lifetime breeding right after producing two live foals.
Outcome. The program was presented as an innovative way to manage participation and loyalty in a volatile Thoroughbred breeding market.
Brand decisions
2018
Campaign Justify through a WinStar-led partnershipProduct launchBackground
Justify had not raced at age two and entered the 2018 season with only a small number of prior starts.
Action taken
The ownership partnership placed Justify with trainer Bob Baffert and campaigned him through the Kentucky Derby, Preakness Stakes, and Belmont Stakes.
Aftermath
Justify became the thirteenth American Triple Crown winner and one of the most commercially valuable stallion prospects of his generation.
2018
Transfer Justify's breeding rights to CoolmoreM&ABackground
Justify retired shortly after completing the Triple Crown, creating substantial demand for his future breeding career.
Action taken
The WinStar-led ownership partnership announced the sale of Justify's breeding rights to Coolmore's Ashford Stud.
Aftermath
Justify moved into Coolmore's stallion operation, while the transaction demonstrated the strategic value of converting racing success into breeding assets.
2013
Expand stallion and training infrastructureStrategyBackground
Growth in the stallion roster and young-horse operation required additional purpose-built facilities.
Action taken
WinStar opened a new stallion barn and maintained expanded turnout, quarantine, breeding, and training facilities.
Aftermath
The farm strengthened its capacity to manage stallions, mares, young horses, and international breeding logistics.
2002
Acquire Tiznow for the stallion programStrategyBackground
Tiznow was a two-time Breeders' Cup Classic winner, although his pedigree was not universally regarded as fashionable.
Action taken
WinStar acquired Tiznow and established him as a cornerstone of its stallion operation.
Aftermath
Tiznow became a leading freshman sire and an important long-term contributor to WinStar's reputation.
2000
Acquire and rebrand Prestonwood FarmStrategyBackground
Kenny Troutt and Bill Casner sought to build a major Thoroughbred breeding and racing operation.
Action taken
They purchased Prestonwood Farm and renamed it WinStar Farm, retaining important bloodstock and expanding the property over time.
Aftermath
The transaction established the foundation of WinStar's integrated breeding, racing, and training business.
Recent events
- 2018
Justify completes the American Triple Crown[1]
Other · Product generation
Justify, owned by a WinStar-led partnership, won the Kentucky Derby, Preakness Stakes, and Belmont Stakes.
- 2018
Justify breeding rights move to Coolmore[1]
M&A · Other
After Justify retired from racing, the ownership partnership announced the sale of his breeding rights to Coolmore's Ashford Stud.
- 2016
WinStar receives Eclipse Award for Outstanding Breeder[1]
Other
WinStar led North American breeders in earnings and major-race results and was recognized as the year's Outstanding Breeder.
- 2013
WinStar opens a new stallion facility[1]
Other
The farm completed a new stallion barn with breeding-shed access, viewing areas, turnout paddocks, and supporting quarantine capacity.
- 2010
WinStar Farm wins Eclipse Award for Outstanding Owner[1]
Other
WinStar received the Eclipse Award for Outstanding Owner after a season highlighted by victories from Super Saver in the Kentucky Derby and Drosselmeyer in the Belmont Stakes.
Sources2 sources
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