After winning the Kentucky Derby with Regret in 1915, Harry Payne Whitney tried to repeat his success again and again. He got as close as third with his two-time champion filly Prudery in 1921, but it was Prudery's son Whiskery that finally turned the trick after a furious stretch duel with Osmand in 1927. In a wide-open year that lacked a truly dominant 3-year-old, Whiskery was rated atop the American sophomore division by most experts. It was all downhill from there for him; he failed to win another stakes race after his 3-year-old season and was gelded after proving sterile when tried at stud as a 4-year-old. He was eventually retired from racing in 1931 and served as a saddle horse at Morven Stud, near Charlottesville, Virginia. He was reportedly euthanized due to a leg injury about 1936, but his death was never officially reported to The Jockey Club and no written records exist to confirm the year of death.
Race record
70 starts, 14 wins, 16 seconds, 8 thirds, US$122,211
1926:
1927:
1928:
Honors
American champion 3-year-old male (1927)
As an individual
A smoothly made brown horse with a long neck, Whiskery became sulky when returned to racing after being tried at stud. This deterioration in his temperament led to his being gelded but failed to make him a more effective racehorse. By the time he retired to Morven Stud, he had apparently acquired a chronic leg injury that continued worsening until he reinjured the bad leg beyond repair while running across a paddock.
Connections
Foaled in Kentucky, Whiskery was bred and owned by Harry Payne Whitney. He was trained by Fred Hopkins at 2 and 3. Whiskery was purchased for US$60,000 by the partnership of Charles A. Stone, Arthur B. Hancock and William Woodward following his 3-year-old season.
Pedigree notes
Whiskery is outcrossed through five generations. He is a full brother to 1928 Preakness Stakes winner Victorian and to multiple stakes winner Halcyon. His dam Prudery is generally considered the American co-champion 2-year-old filly of 1920 and the American champion 3-year-old filly of 1921 and is a full sister to 1922 Coaching Club American Oaks winner Prudish (dam of the stakes-winning Chicle colt Comstockery and second dam of multiple stakes winners Haltal, Very Snooty and Beldine) and the good stakes winner Macaw. Prudery is also a half sister to Polly Pennant (by Peter Pan's son Pennant), dam of stakes winner Infinity (by Eternal); second dam of 1946 Mexican Horse of the Year Plucky Flag, 1942 Ashland Stakes winner The Swallow, and the multiple stakes-winning steeplechaser Torturer; and third dam of three-time Mexican champion older female Plucky Raf. Another half sister to Prudery, Tonala (by Broomstick), is the third dam of three-time American champion steeplechaser Neji and 1963 American champion grass horse Mongo.
Prudery's dam Polly Flinders (by Burgomaster) is a full sister to juvenile stakes winner Slipshod and a half sister to 1913 Preakness Stakes winner Buskin (by Burgomaster's sire Hamburg). She is also a half sister to multiple stakes producer Comfort (by Broomstick). Polly Flinders was produced from Slippers (by Meddler), the most important daughter of the great 19th-century matron Cinderella (by Blue Ruin or Tomahawk).
Books and media
Last updated: August 19, 2023
Race record
70 starts, 14 wins, 16 seconds, 8 thirds, US$122,211
1926:
- Won Ardsley Handicap (USA, 8f+70yD, Empire City)
- 2nd Endurance Handicap (USA, 8FD, Bowie)
- 3rd Pimlico Futurity (USA, 8FD, Pimlico)
1927:
- Won Kentucky Derby (USA, 10FD, Churchill Downs)
- Won Twin City Handicap (USA, 10FD, Belmont)
- Won Stanley Produce Stakes (CAN, 10FD, Old Woodbine)
- Won Chesapeake Stakes (USA, 8.5FD, Havre de Grace)
- Won Huron Handicap (USA, 9.5FD, Saratoga)
- 2nd Fairmount Derby (USA, 10FD, Fairmount Park)
- 2nd Maryland Handicap (USA, 10FD, Laurel)
- 2nd Potomac Handicap (USA, 8.5D, Havre de Grace)
- 3rd Preakness Stakes (USA, 9.5FD, Pimlico)
- 3rd Prince George Handicap (USA, 8.5FD, Bowie)
1928:
- 3rd Whitney Stakes (USA, 10FD, Saratoga)
Honors
American champion 3-year-old male (1927)
As an individual
A smoothly made brown horse with a long neck, Whiskery became sulky when returned to racing after being tried at stud. This deterioration in his temperament led to his being gelded but failed to make him a more effective racehorse. By the time he retired to Morven Stud, he had apparently acquired a chronic leg injury that continued worsening until he reinjured the bad leg beyond repair while running across a paddock.
Connections
Foaled in Kentucky, Whiskery was bred and owned by Harry Payne Whitney. He was trained by Fred Hopkins at 2 and 3. Whiskery was purchased for US$60,000 by the partnership of Charles A. Stone, Arthur B. Hancock and William Woodward following his 3-year-old season.
Pedigree notes
Whiskery is outcrossed through five generations. He is a full brother to 1928 Preakness Stakes winner Victorian and to multiple stakes winner Halcyon. His dam Prudery is generally considered the American co-champion 2-year-old filly of 1920 and the American champion 3-year-old filly of 1921 and is a full sister to 1922 Coaching Club American Oaks winner Prudish (dam of the stakes-winning Chicle colt Comstockery and second dam of multiple stakes winners Haltal, Very Snooty and Beldine) and the good stakes winner Macaw. Prudery is also a half sister to Polly Pennant (by Peter Pan's son Pennant), dam of stakes winner Infinity (by Eternal); second dam of 1946 Mexican Horse of the Year Plucky Flag, 1942 Ashland Stakes winner The Swallow, and the multiple stakes-winning steeplechaser Torturer; and third dam of three-time Mexican champion older female Plucky Raf. Another half sister to Prudery, Tonala (by Broomstick), is the third dam of three-time American champion steeplechaser Neji and 1963 American champion grass horse Mongo.
Prudery's dam Polly Flinders (by Burgomaster) is a full sister to juvenile stakes winner Slipshod and a half sister to 1913 Preakness Stakes winner Buskin (by Burgomaster's sire Hamburg). She is also a half sister to multiple stakes producer Comfort (by Broomstick). Polly Flinders was produced from Slippers (by Meddler), the most important daughter of the great 19th-century matron Cinderella (by Blue Ruin or Tomahawk).
Books and media
- “Whiskery—an Old Soldier” is the 14th chapter in Jim Bolus' Derby Magic (1997, Pelican Publishing Company).
- Whiskery is profiled in Chapter 5 of Avalyn Hunter's American Classic Pedigrees 1914-2002 (2003, Eclipse Press).
Last updated: August 19, 2023