Gallant Man
Winfrey trained his first stakes winner in 1931, sending out Charon to win the Myrtle Claiming Stakes at Aqueduct. His other stakes winners included Dedicate, Squared Away, Bulwark, Aboyne, Martyr, and Son of Erin. Squared Away won stakes in five seasons, while Dedicate was the U. S. Champion Handicap Horse of 1957. That year, he defeated Gallant Man and Bold Ruler in the Woodward Stakes.