Sir Winston (foaled April 8, 2016) is an American Thoroughbred racehorse who won the 2019 Belmont Stakes. Background Sir Winston is a chestnut colt who was bred in Kentucky by Tracy Farmer. He was offered for sale at the 2017 Keeneland Yearling Sales but the top bid of $50,000 did not meet his reserve, and thus races as a homebred for Farmer. He is trained by Mark Casse. Sir Winston was sired by Awesome Again, who won the Queen's Plate and Breeders' Cup Classic during his racing career. His leading runners include Ghostzapper, Oxbow, Game On Dude, Ginger Punch, and Paynter. Sir Winston's dam, La Gran Bailadora, is a stakes-winning daughter of Afleet Alex, who won the Preakness and Belmont in 2005. Racing career 2018: two-year-old season Sir Winston made his first start on June 14, 2018, in a maiden special weight race at Churchill Downs. He broke slowly and was "done early" according to the official chart, finishing sixth. He finished ninth in his next start, on July 21 at Saratoga, before recording his first win on September 12 at Woodbine, a dead heat with Inclusive. Sir Winston made his graded stakes debut in the Grey Stakes at Woodbine on October 21. He settled a few lengths behind the early pacemakers then started his move on the far turn, racing five wide. He closed ground "gamely" and finished third. He made his final start of the year on December 8 in the listed Display Stakes at Woodbine. He stalked the early pace, then moved to the lead as the field turned into the homestretch. He held off a late run from Inclusive to win by a length. 2019: three-year-old season Sir Winston started his three-year-old season as a "mystery horse" for Casse, who noted the colt's wins at age two had come over a synthetic surface at Woodbine. "We're not really sure how we'll run on the dirt," Casse said. To test the colt, he entered him in the Withers Stakes at Aqueduct on February 2, 2019. Sir Winston broke slowly and trailed the field early before closing well down the stretch to finish fourth. He then finished fifth in the Tampa Bay Derby on March 9. In a last attempt to qualify on the 2019 Road to the Kentucky Derby, Sir Winston was entered in the Blue Grass Stakes at Keeneland on April 4. He was bumped at