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Twenty years into his retirement from a Hall of Fame career in college basketball, Denny Crum was at the Keeneland sales pavilion shopping for a stakes winner with trainer Dallas Stewart.

This was no new venture for Crum, who had been a racehorse owner since the mid-1970s and bred nearly a dozen winners through the late 1980s and ‘90s. Thoroughbred racing was yet another outlet for the man who loved to compete, whether it was basketball, golf, fishing, horse racing, or poker.

Behind every horse at this year’s Kentucky Derby Presented by Woodford Reserve was an owner or a group of owners whose dreams were realized once the gate doors opened for the 149th run for the roses. Three high-profile owners, in particular, got to experience the thrill of having a horse in the race for the first time.

When Sir Barton became the first horse to win the Kentucky Derby, Preakness Stakes, and Belmont Stakes in 1919, he created an elite standard that only 12 other horses have matched since.

Season 2 of “Stake in Stardom,” the America’s Best Racing initiative in which brand ambassadors become minority stake owners in an elite Thoroughbred, is underway. This year’s roster includes a few familiar faces from last season in addition to several new personalities eager to experience the sport and lifestyle of horse racing up close.

NBC Sports football analyst Matthew Berry will join the network’s coverage of the 149th Kentucky Derby presented by Woodford Reserve, Saturday, May 6 at Noon ET on NBC and Peacock, offering his unique insight on horse racing’s biggest event. “Handicapping 101 with Matthew Berry” will provide a lighthearted look at the basics of betting the races.

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