Texas-based owner/breeder Kenny Troutt loves a challenge.
After building a multi-level marketing telecommunications company from scratch with longtime partner Bill Casner and others, he set his sights on establishing a full-service Thoroughbred breeding and racing operation that could not only compete at the top of the game but also be a successful business venture.
This year, that venture—called WinStar Farm—celebrates its 25th anniversary having accomplished all of the goals Troutt set out to achieve.
Troutt doesn't have a dip-your-toe-in-water personality. He does the research and then dives in, which he did in February 2000 when he and Casner bought Prestonwood Farm—400 acres, a small broodmare band, and stallions Distorted Humor, Groovy, Kris S., and Victory Gallop.
Troutt and Casner had been partners in racing since the mid-1970s when they both showed up at the claiming box at Ak-Sar-Ben Racetrack for a son of Gallant Man named Great Bear Lake, who was a stakes winner and had placed third in the 1972 Arkansas Derby.
Troutt, who grew up in Mount Vernon, Ill., was introduced to horse racing by an uncle in 1965. While attending Southern Illinois University, he made frequent trips to Churchill Downs and witnessed the Kentucky Derby (G1) victories of Secretariat and Riva Ridge.
Casner grew up in El Paso, Texas, and galloped horses at Sunland Park. He became a full-time trainer after college and trained for Troutt until they shifted their business interests to Excel Communications, which at one point was the fifth-largest long-distance carrier in the United States and became the youngest company to be listed on the New York Stock Exchange. Their focus returned to Thoroughbreds after 1998 when Excel merged with Teleglobe in a $3.1 billion deal.
Troutt remembers being at Saratoga Race Course in 1999 with Texas oilman Art Preston, who owned Prestonwood with his brothers Jack and J.R., to watch Victory Gallop win the Whitney Handicap (G1).
"That was my first trip to Saratoga, and I loved it," Troutt recalled. "I loved the fact that there were three generations of the Farishs and Phipps playing together and having fun. That's when I decided to get in."
But Troutt and Casner were returning to the game wiser.
"We learned how not to do this business, and that was at the low end of the game," Casner told the New York Times in May 2010. "We also knew that horses are volatile and fragile commodities, and losing money is no fun. So, we needed to be profitable to survive. We are not a folly; this is not a plaything."
In addition to focusing on quality, Troutt said he soon recognized the operation needed to be much larger in scope.
"We started with a select few mares and a few stallions. I soon realized that scale was needed to be successful," Troutt said. "So, we ramped up to 120 mares and 15 stallions, plus or minus. You need quality and numbers to make it work."
Elliott Walden, who trained Victory Gallop and joined WinStar as its private trainer in 2002, said it was apparent from the start that Troutt and Casner were taking a different approach than most to the new venture.
"Especially Kenny when he talked about the scale of things, you could tell that it didn't shake him. He was all about bigger is better," said Walden, who is now WinStar's president, CEO, and racing manager. "He's a guy who, when he does something, he goes all in. He did that with Excel Communications, and he did that with his AAU basketball team, Texas Titans. He was the first guy (in the league) to hire a college coach and brought in a life coach and a skills coach. So, it's been exciting for me to be a part of seeing his vision come together."
As a breeding operation, WinStar first broke into the top five among North America's leading breeders in 2006 with more than $5.2 million in earnings. By 2010, WinStar would celebrate one of Troutt and Casner's key goals for the farm—racing a homebred Kentucky Derby (G1) winner. Super Saver, a son of Maria's Mon out of the A.P. Indy mare Supercharger, delivered the win with trainer Todd Pletcher.
"When we started, I wanted to win the Kentucky Derby, and I remember we bred five to eight mares to Storm Cat because he was the best stallion when I started. He was standing for $500,000 at the time," Troutt said. "But besides wanting to win the Derby, I was continually motivated to make the farm work because people used to tell me, you can't make it in the horse business. I am proud of the fact we have been profitable."
WinStar would quickly check off another accomplishment on the wish list when Drosselmeyer won the 2010 Belmont Stakes (G1). Though not a homebred, the colt by Distorted Humor would add laurels to the farm's breeding program. Drosselmeyer kept the momentum rolling by capturing the Breeders' Cup Classic (G1) the following year.
In addition to its accomplishments, 2010 was a year of change for WinStar. Troutt took over as sole owner of the farm.
"The dissolution of my partnership with Kenny is a business strategy that is mutually beneficial at this point in our lives," Casner said at the time. "The relationship that Kenny and I have remains unchanged, and we are still the closest of friends.
"Susan and I will continue to keep our mares at WinStar, employ the training division for our young horses, and participate in future partnerships with Kenny. The evolution of WinStar over the last 10 years and the relationship that we have had with the entire WinStar team has been one of the most gratifying experiences that Susan and I have ever experienced. We will continue to be heavily involved in racing, breeding, and all efforts to move our industry forward."
Troutt kept WinStar on a growth path. The farm has grown to 2,200 acres with another 260 acres leased. WinStar also developed a training center that had not been part of the original vision but evolved from the breeding and racing operation. The nearly seven-furlong track has turns with a radius comparable to a one-mile track and has a dirt surface of the same composition as Keeneland's main track.
"One of our goals at WinStar has also been to improve where we can improve and we felt this was a good opportunity, an investment, to do something that somebody else didn't have," Walden said. "There are plenty of good stud nurseries and plenty of good farms raising good horses but not many with a training center of the scale we built."
"As I said earlier, we adapted to create more scale," Troutt said. "Along with that, we built a training center on the farm in 2010. We flew to Europe and saw Ballydoyle, Chantilly, and Newmarket. Whenever I have done something, I have always tried to go all in. It is a blessing and a curse."
The training center would help Troutt achieve one of his biggest dreams—to race a Triple Crown winner.
In 2016, WinStar's Maverick Racing arm and China Horse Club paid $500,000 for a son of Scat Daddy who was bred and sold by John D. Gunther's Glennwood Farm. The strapping chestnut colt named Justify would receive his early training lessons at the WinStar training center before getting shipped to trainer Bob Baffert.
SF Racing, Head of Plains Partners, and Starlight Racing would later join Justify's ownership group that celebrated the colt's undefeated campaign at 3 that included the 2018 Kentucky Derby, Preakness Stakes (G1), and Belmont.
"Kenny always believed we would win the Triple Crown and, quite honestly, I didn't have that same belief because I felt it was too unattainable," Walden said. "But every year if a Derby winner got beat in the Preakness, he'd say, well there is another one waiting for us to win the Triple Crown. He almost spoke it into existence."
Besides Super Saver and Justify, WinStar has had a good run through the Triple Crown races as an owner and/or breeder. The farm bred 2003 Kentucky Derby and Preakness winner Funny Cide (by Distorted Humor) and 2020 Preakness winner Swiss Skydiver (by Daredevil ), the sixth filly to win the second jewel of the Triple Crown. As owner, WinStar won the 2016 Belmont Stakes with Creator, a son of Tapit the farm raced in partnership with celebrity chef Bobby Flay.
In 2016, WinStar topped the leading North American breeders' standings for the first time with more than $10.5 million in earnings and earned its first Eclipse Award title as outstanding breeder. The farm was represented that year by Breeders' Cup Mile (G1T) winner Tourist, whom they also raced in partnership,and Breeders' Cup Juvenile Fillies Turf (G1T) winner New Money Honey along with seven other graded stakes winners.
The farm would be the country's leading breeder by earnings again in 2018 with more than $8.76 million in purses, but the Eclipse trophy for that year went to Glennwood Farm owner John Gunther, who bred Justify. WinStar would earn a second Eclipse outstanding breeder title in 2020 as the breeder of Swiss Skydiver and Shedaresthedevil, who won the Kentucky Oaks (G1).
WinStar-bred horses in 2003-24 captured 3,266 wins and earned more than $144.8 million in the United States and Canada.
As an owner, WinStar in its name alone has won 550 races and earned more than $41.3 million, according to Equibase. The farm's involvement in more than 150 partnership groups since 2000 has made a significantly bigger impact. With partners, WinStar has celebrated another 581 wins and captured more than $64.5 million in earnings.
Walden said he attributes WinStar's continued success to Troutt's willingness to take bad news better than good news and to have enough faith in the farm's team members to let them make decisions.
"If we are in a crisis, he has learned to settle and take the emotion out of it and really think about what the next steps should be," he said. "And he doesn't play the blame game. The biggest driver of success is the ability to make a decision, and he gives you great confidence to make a decision. If the decision is wrong, then we adapt, regroup, and move forward."
Troutt distilled the success of WinStar down to four key ingredients: work with strategic partners, like Teo Ah Khing's China Horse Club; build a high-quality stallion roster because stallions are a cornerstone; build a strong racing program because that is the best avenue to make stallions; and, keep your horse population consistent to keep costs under control.
"If you do those things, you can make it work," he said. "Is there still more to accomplish? Yes, win another Triple Crown!"
