Terry Finley (OPM 45, 2014) has been in the winner’s circle of more than a few race tracks. Founder and CEO of West Point Thoroughbreds, Finley even won the 2017 Kentucky Derby with his partial ownership of Always Dreaming (an experience he describes in this episode of the Skydeck podcast). On November 5, Finley took a trip to the winner’s circle again—this time with Flightline, an undefeated four-year-old who won the $6 million Breeders’ Cup Classic in Lexington, Kentucky, with an effortless 8¼-length margin.

Finley’s business, West Point Thoroughbreds, offers partial shares of horses as a way to participate in the once-exclusive sport of racing. That model also applies to Flightline, purchased for $1 million by a West Point consortium; by the time he won the Breeders’ Cup, that ownership had extended to four other partners, including Hronis Racing, Summer Wind Equine, Siena Farm, and Woodford Racing. Two days after the Breeders’ Cup, with Flightline’s retirement announced (he will stand at stud at Woodford Racing), Finley sold 2.5 percent of West Point’s 17.5 percent share (which is further distributed amongst seven owners) for $4.6 million; at that price, Flightline’s total value would be a whopping $184 million.

Days before the Breeders’ Cup, Finley reflected on how he managed to purchase a horse that many are comparing to all-time greats like Man O’ War and Secretariat. After winning the Kentucky Derby, Finley said, he started to think about West Point Thoroughbred’s future. “I wanted to shoot for glory,” he told the Philadelphia Inquirer. Flightline’s higher price tag was a risk, but respected Kentucky bloodstock agent David Ingordo had been watching the horse from the very beginning; when he called Finley to put together a partnership, it was an easy sell, especially after Finley saw Flightline at a sale in Saratoga: “Damn, that’s how they’re supposed to look,” he recalls thinking. (Finley shares his tips for “How to Pick a Winner” in this Bulletin article.)

“I had never seen a horse move like him,” Finley said of watching Flightline in action. “He just never seems to be doing it with any ounce of effort. It’s just there, a gift from God.”

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