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Perry was a three-time All-Star and won the 1970 AL Cy Young Award, when he posted a record of 24-12. Jim and Gaylord Perry are the only brothers in Major League history to win Cy Young Awards. He also won 20 games in 1969, and won at least 17 games five times. As a batter, Perry was a switch-hitter and posted a respectable .199 batting average in his career. On July 3, 1973, brothers Gaylord Perry (Indians) and Jim Perry (Tigers) pitched against each other for the only regular season game in their careers. Neither finished the game, but Gaylord was charged with the 5–4 loss. Two Norm Cashhome runs helped Detroit.
Following his final year with Oakland, Perry retired to his North Carolina home where he keeps busy with charitable events, especially golf tournaments. His son, Chris, is a professional golfer who has won a tournament on the PGA Tour.