Sir Winston

Sir Winston, upset winner of the 2019 Belmont Stakes Presented by NYRA Bets, began his racing career with two consecutive losses on dirt and turf before breaking through once shipped to Woodbine. Racing on the synthetic Tapeta main track, the son of Awesome Again won his third start, finished third in a Grade 3 stakes, and then won a listed stakes.

He returned in 2019 and was put on the Triple Crown trail by trainer Mark Casse, but the colt finished fourth, fifth, and seventh in Kentucky Derby Presented by Woodford Reserve points races. He then targeted the Grade 3 Peter Pan Stakes on May 11 at Belmont, and showed signs of rounding into form with a fast-closing second to Global Campaign.

Sir Winston left the Belmont Stakes starting gate as the “other” Mark Casse horse besides Preakness Stakes winner War of Will. With Joel Rosario aboard for the second straight race following the Peter Pan, Sir Winston saved ground through both of Belmont Park’s sweeping turns and then angled out in early stretch. He continued strongly to the finish and held off Wood Memorial Stakes Presented by NYRA Bets winner and Kentucky Derby Presented by Woodford Reserve third-place finisher Tacitus by a length, giving Casse his first Belmont Stakes victory.

Sir Winston was unplaced in his final start in 2019.

In 2020, Sir Winston won one of four starts, an allowance-optional claiming race in January at Aqueduct, and finished second in the Flat Out Stakes at Belmont Park.

As a 5-year-old in 2021, Sir Winston opened the season with an allowance win on the synthetic main track at Woodbine before back-to-back runner-up finishes in the Grade 3 Durham Cup Stakes and Grade 2 Autumn Stakes, beaten by less than a length in both races on the Woodbine main track. Sir Winston banked another stakes win Dec. 5, 2021, when he held on for a half-length victory in the Grade 3 Valedictory Stakes going 1 ½ mile on the all-weather surface at Woodbine.

Sir Winston is owned by Kentucky native Tracy Farmer, who won the Belmont with his third career starter in the race. He is out of the Grade 3-winning Afleet Alex mare La Gran Bailadora.