[1] Sir Winston was sired by Awesome Again, who won the Queen's Plate and Breeders' Cup Classic during his racing career.
[2] Sir Winston's dam, La Gran Bailadora, is a stakes-winning daughter of Afleet Alex, who won the Preakness and Belmont in 2005.
[4] He finished ninth in his next start, on July 21 at Saratoga,[1] before recording his first win on September 12 at Woodbine, a dead heat with Inclusive.
[7] 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.
Sir Winston broke slowly and trailed the field early before closing well down the stretch to finish fourth.
[1] 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 circled six-wide around the final turn, then closed steadily down the stretch to finish second, beaten only 1+1⁄4 lengths by Global Campaign.
Ridden for the first time by Joel Rosario, Sir Winston broke slowly from post position 7 and moved over to the rail to save ground around the first turn.