Faded Glory: Forgotten Kentucky Derby Winners (Whiskery, 1927)

The history of the Kentucky Derby is rich with names that have left their mark on this classic race: Bradley, Woodward, Chenery, and Whitney, owners who all celebrated more than one victory of their own. The Whitney family’s connection to the Run for the Roses spans more than a century, with four wins from their long list of starters. 

Whiskery was one of those winners, his pedigree as rich as his owner, replete with classic winners on both sides, his stamina and heart deep enough to triumph in America’s signature classic. 

Solid Foundation

A son of financier and diplomat William Collins Whitney, businessman Harry Payne Whitney inherited both a love of equine sports and the fortune to pursue them from his father, building a major breeding and racing operation in the early decades of the 20th century. His filly Tanya won the 1905 Belmont Stakes and then Regret bore the Whitney colors into the Kentucky Derby winner’s circle in 1915, becoming the first filly to win the Bluegrass classic.

“Isn’t she the prettiest filly you ever saw? You know, this is the greatest race in America at the present time, and I don’t care if she ever starts again,” Whitney said after the Derby. “The glory of winning this event is big enough.” Her victory made the Derby a race owners and trainers everywhere wanted to win, including Whitney himself, who sent 16 horses to Louisville in pursuit of another victory, coming up short each time. 

One of those was a lovely brown filly named Prudery. A daughter of Belmont Stakes winner Peter Pan, she won stakes at two and three, with both the Spinaway and the Alabama as well as seconds in the Kentucky Oaks and the Travers Stakes and a third in the Derby on her resume. For her first foal, Whitney paired her with his record-setting stallion Whisk Broom II to produce a lithe brown colt with a blazed face and two hind socks. From Whisk Broom II and Prudery would come the name Whiskery. 

Toward the end of his juvenile season in 1926, he got his first stakes victory in the Ardsley Handicap at Empire City after in-the-money finishes in the Endurance Handicap and the Pimlico Futurity. Entering 1927, Whiskery stood alongside his stablemate Bostonian as the Whitney stable’s hopes for the classic season. 

Dramatic Derby

The Preakness Stakes was first that year, 12 horses meeting the starter on May 9, including both Whiskery and Bostonian. The pair sat midpack until the six-furlong mark as Charles Kurtsinger sent Whiskery after the leaders. He led briefly in the stretch and then tired as Bostonian came on with a rush. Whiskery hit the wire in third, less than a length behind his victorious stablemate. Five days later, the two were in Louisville to pursue another Kentucky Derby victory for the prominent breeder and owner. 

Whiskery almost did not make it to the starting line: as he exited his stall, the colt nearly got his leg trapped in the space between the door and its frame. A groom caught the incident before it could cause damage to the Whisk Broom II colt, saving his chance at roses. With jockey Linus McAtee in the saddle, Whiskery stood in post 7, the middle of the field of 15 horses, and got away quickly to find a running position midpack. At the mile mark, he was third behind Jock and Osmand, who had future Hall of Fame jockey Earl Sande in the saddle. In the stretch, McAtee sent Whiskery after the leaders, finally pulling even with Osmand as Jock tired. 

Their lack of forward progress puzzled McAtee until he looked down to see that Sande had hooked his leg around McAtee’s and was grabbing his stirrup in the race’s final yards. The veteran jockey was close to falling off, but he was able to keep his seat and finally shook free of Sande to win by a head. Whiskery gave Whitney his much-desired second victory in the classic stakes and McAtee gave Sande a piece of his mind back in the jock’s room. “It’s a good thing I won, or I’d kill you sure as hell,” the winning rider told his nemesis after the race. 

Harry Payne Whitney had traveled from New York to watch his two colts take their shot at roses and had done so while suffering from a terrible cold. When a shower opened up over Churchill Downs, he left for the dry safety of his railcar, leaving his son C.V., better known as Sonny, as his deputy for the victory ceremony. Sonny too missed the trophy presentation after becoming trapped in the surging crowd exiting the racetrack. 

Later that evening, Sonny returned to his father’s Lexington farm and saw a crowd of workers standing around a bonfire celebrating Whiskery’s win. In the firelight, Whitney saw the silhouette of a horse and soon learned that Regret had been brought out of her stall to join the celebrants, quietly taking in the night’s festivities. 

Whitney Winner 

Whiskery’s career peaked with his Derby win. He raced for another season and then retired to stud; William Woodward, Arthur B. Hancock, and Charles Stone bought the colt for $60,000 but the Derby winner proved to be infertile. He was gelded and returned to the races to no avail. Whiskery eventually became a saddle horse for Stone, living out his days at Morven Stud in Virginia. Around 1936, the 1927 Derby winner aggravated an old leg injury in a paddock accident and was put down, the date of his death and burial place lost to time. 

His name may not be as familiar as that of another Whitney winner, Regret, but Whiskery’s 1927 victory helped Harry Payne Whitney reach his goal of a second Kentucky Derby, another of his dozen Triple Crown classic wins.