Olwine played college baseball for Morehead State University. In 1978 and 1979, he played collegiate summer baseball with the Hyannis Mets of the Cape Cod Baseball League, where he was the winning pitcher in the league's 1979 all-star game at Fenway Park, and helped Hyannis win the league championship in both seasons.
He was signed by the New York Yankees as an amateur free agent in 1980. Olwine played his first professional season with their Rookie league Paintsville Yankees, Class A (Short Season) Oneonta Yankees, and Class A-Advanced Fort Lauderdale Yankees in 1980, and his last season with the Braves' Triple-A unit, the Richmond Braves, in 1988.
Olwine shares the major league baseball record for most games pitched without a win, at 80.

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