Wineapple was born in Boston, Massachusetts, and was Jewish. He attended Syracuse University for his college freshman year, then transferred to Providence College, where he was a star basketball player for three years. A first-team All-American his senior year, he led the 1928-29 team to a 17-3 record and was the second-leading scorer in the nation.
His lone major league appearance came on September 15, 1929, in the Senators' 16–2 loss to the Detroit Tigers at Griffith Stadium. He took the mound in the sixth inning with the Tigers already holding a 12–2 lead, entering the game as part of a double switch in which he took the place of Baseball Hall of Fame shortstop Joe Cronin in the Washington lineup. Wineapple hurled the final four innings in relief, giving up four runs (two earned) on seven hits, walking three and striking out one against a Tigers lineup that featured Hall of Famer Charlie Gehringer.
From 1928 to 1931, he played summer baseball in the Cape Cod Baseball League (CCBL), where it was reported that Wineapple "seems to play baseball as he does basketball...with his heart in it all the time. He is pitching and hitting exceptionally well." Wineapple played for the CCBL's Osterville town team from 1928 to 1930, and for the Orleans team in 1931.

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