Winters was one of the Negro Leagues‘ best lefthanded pitchers. The ace curveballer starred in the first modern Black World Series in 1924 as a member of the Hilldale club. Backed by Hall of Famers Judy Johnson and Pop Lloyd and stalwarts Frank Warfield and Biz Mackey, Winters went 3-1 (1.16) versus the Kansas City Monarchs. He led the Eastern Colored League with marks of 26-4 in 1924, 21-10 in 1925, and 18-6 in 1926. In barnstorming games against Babe Ruth‘s All Stars, Winters split two decisions with Lefty Grove.