In 1951, Winkles played his first season of professional baseball in the Chicago White Sox organization. He played 7 more seasons in the minor leagues, spending time in Chicago Cubs and Philadelphia Phillies organizations before retiring from playing after the 1958 season.
In 1959, Winkles became the first head coach of the Arizona State University Sun Devils baseball team. He continued coaching at ASU through 1971, compiling a 524-173 (.751) win-loss record.
Winkles began coaching in professional baseball in 1972 with the California Angels. He became one of only two major league managers ever born in Arkansas in 1973 when he was given the head job of the Angels in 1973. He also managed the Angels in 1974 and the Oakland Athletics from 1978-1979. Winkles finished his managerial career with a 109-127 win-loss record.
In 2006, Winkles was elected to the Collegiate Baseball Hall of Fame as a member of the hall of fame's inaugural class.
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