Scouted by Branch Rickey and George Sisler, Wickersham was signed by the Pirates in 1955 but was acquired by Kansas City in the 1959 minor league draft. Slowed by a back injury in 1961, he went 11-4 in 1962 and 12-15 in 1963 and was a major figure in the deal that brought Rocky Colavito to the A’s. He responded with his best season for Detroit in 1964, going 19-12 and missing a 20-win season only because of his first ejection from a ballgame; he tied for third in the AL in wins and had a 3.44 ERA.