Sir Winston (USA)
April 8, 2016 – Living
Awesome Again (CAN) x La Gran Bailadora (USA), by Afleet Alex (USA)
Family 1-n
April 8, 2016 – Living
Awesome Again (CAN) x La Gran Bailadora (USA), by Afleet Alex (USA)
Family 1-n
Not one of the more distinguished Belmont Stakes (USA-G1) winners in history, Sir Winston won the 2019 renewal on superior stamina at 10-1 odds. He continued racing through age 5 and added a Grade 3 win in Canada to his resume before retiring to stallion duty.
Race record
20 starts, 6 wins, 4 seconds, 1 third, US$1,277,623
2018:
2019:
2020:
2021:
Assessments
Rated at 116 pounds on the 2019 Longines World’s Best Racehorse Rankings, 12 pounds below co-highweights Crystal Ocean (a multiple European highweight over 9.5 to 14 furlongs), Enable (the European Horse of the Year), and Waldgeist (winner of the Prix de l’Arc de Triomphe, FR-G1).
As an individual
A well-balanced, short-coupled chestnut horse with a nice shoulder, Sir Winston lacked tactical speed and typically did his best running from off the pace. He suffered an ankle injury either during the Belmont or shortly afterward that kept him away from the races for six months. Trainer Mark Casse described him as having “an excellent mind.”
As a stallion
Sir Winston entered stud in Kentucky at Crestwood Farm in 2023. His first foal, a filly out of the winning Hard Spun mare Pretty Clever, was born on January 30, 2024, at Tracy Farmer’s Shadowlawn Farm.
Connections
Sir Winston was bred and owned by Tracy Farmer and was trained by Mark Casse. He was ridden to his Belmont Stakes win by Joel Rosario. The horse entered stud in 2023 in Kentucky at Crestwood Farm.
Pedigree notes
Sir Winston is inbred 3x5 to 13-time Canadian champion sire Vice Regent, 4x5 to two-time American champion sire Mr. Prospector, and 5x5 to Mr. Prospector’s sire, 1963 American co-champion 2-year-old male Raise a Native. He is a half brother to Spanish Star (by Blame), dam of 2022 Franklin-Simpson Stakes (USA-G2) winner One Timer (by Trappe Shot), Grade 1-placed listed stakes winner Just Basking (by Arrogate), and juvenile stakes winner Kilwin (by Twirling Candy).
The dam of Sir Winston, La Gran Bailadora, won the 2011 Distorted Humor Kentucky Cup Distaff Stakes (USA-G3) and was Grade 1-placed. She is out of the stakes-winning Affirmed mare Affirmed Dancer, whose dam Woolloomooloo (by 1988 Canadian champion 3-year-old male Regal Intention) won two listed Canadian stakes races as a 5-year-old.
Produced from Tintaburra (by multiple Canadian stakes winner Bold Agent, by Bold Bidder), Woolloomooloo is a half sister to Caandian restricted stakes winner Guida Might (by Seattle Dancer) and to Tinted Ivory (by Sir Ivor), dam of juvenile restricted stakes winner Mr. Fixed Income (by Sahm). Woolloomooloo is also a half sister to Matilda Dancer (by Green Dancer), dam of stakes winner Diamond Lucy (by Lewis Michael), and to Sheila’s Ovation (by Roar), dam of multiple Chilean Group 3 winner Shanghai (by Shanghai Bobby).
Fun facts
Last updated: May 23, 2025
Race record
20 starts, 6 wins, 4 seconds, 1 third, US$1,277,623
2018:
- Won Display Stakes (CAN-L, 8.5FD, Woodbine)
- 3rd Grey Stakes (CAN-G3, 8.5FD, Woodbine)
2019:
- Won Belmont Stakes (USA-G1, 12FD, Belmont)
- 2nd Peter Pan Stakes (USA-G3, 9FD, Belmont)
2020:
- 2nd Flat Out Stakes (USA-L, 11FD, Belmont)
2021:
- Won Valedictory Stakes (CAN-G3, 12FA, Woodbine)
- 2nd Autumn Stakes (CAN-G2, 8.5FA, Woodbine)
- 2nd Durham Cup Stakes (CAN-G3, 8.5FA, Woodbine)
Assessments
Rated at 116 pounds on the 2019 Longines World’s Best Racehorse Rankings, 12 pounds below co-highweights Crystal Ocean (a multiple European highweight over 9.5 to 14 furlongs), Enable (the European Horse of the Year), and Waldgeist (winner of the Prix de l’Arc de Triomphe, FR-G1).
As an individual
A well-balanced, short-coupled chestnut horse with a nice shoulder, Sir Winston lacked tactical speed and typically did his best running from off the pace. He suffered an ankle injury either during the Belmont or shortly afterward that kept him away from the races for six months. Trainer Mark Casse described him as having “an excellent mind.”
As a stallion
Sir Winston entered stud in Kentucky at Crestwood Farm in 2023. His first foal, a filly out of the winning Hard Spun mare Pretty Clever, was born on January 30, 2024, at Tracy Farmer’s Shadowlawn Farm.
Connections
Sir Winston was bred and owned by Tracy Farmer and was trained by Mark Casse. He was ridden to his Belmont Stakes win by Joel Rosario. The horse entered stud in 2023 in Kentucky at Crestwood Farm.
Pedigree notes
Sir Winston is inbred 3x5 to 13-time Canadian champion sire Vice Regent, 4x5 to two-time American champion sire Mr. Prospector, and 5x5 to Mr. Prospector’s sire, 1963 American co-champion 2-year-old male Raise a Native. He is a half brother to Spanish Star (by Blame), dam of 2022 Franklin-Simpson Stakes (USA-G2) winner One Timer (by Trappe Shot), Grade 1-placed listed stakes winner Just Basking (by Arrogate), and juvenile stakes winner Kilwin (by Twirling Candy).
The dam of Sir Winston, La Gran Bailadora, won the 2011 Distorted Humor Kentucky Cup Distaff Stakes (USA-G3) and was Grade 1-placed. She is out of the stakes-winning Affirmed mare Affirmed Dancer, whose dam Woolloomooloo (by 1988 Canadian champion 3-year-old male Regal Intention) won two listed Canadian stakes races as a 5-year-old.
Produced from Tintaburra (by multiple Canadian stakes winner Bold Agent, by Bold Bidder), Woolloomooloo is a half sister to Caandian restricted stakes winner Guida Might (by Seattle Dancer) and to Tinted Ivory (by Sir Ivor), dam of juvenile restricted stakes winner Mr. Fixed Income (by Sahm). Woolloomooloo is also a half sister to Matilda Dancer (by Green Dancer), dam of stakes winner Diamond Lucy (by Lewis Michael), and to Sheila’s Ovation (by Roar), dam of multiple Chilean Group 3 winner Shanghai (by Shanghai Bobby).
Fun facts
- Sir Winston was named in honor of Sir Winston Churchill, Prime Minister of the United Kingdom in 1940-1945 and 1951-1955 and a pivotal figure of the World War II era.
- Tracy Farmer was lucky to keep Sir Winston, as the horse failed to make his reserve on a US$50,000 bid at the 2017 Keeneland September yearling sale.
- Sir Winston’s winning move in the Belmont Stakes was at the expense of his stablemate, Preakness Stakes (USA-G1) winner War of Will, as he just beat War of Will to the same small hole to the outside that War of Will was aiming for. Shut off and traveling over a surface he apparently did not care for, War of Will ended up ninth.
Last updated: May 23, 2025