Early in the 1955 season, Herbert was sold to the Athletics, where he was a starter and reliever for the next several seasons (although he would spend the entire 1956 and 1957 seasons in triple-A).
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Midway through the 1961 season, the Athletics traded Herbert to the White Sox in a 4-for-4 deal. He was strictly a starting pitcher in Chicago. In 1962 Ray won 20 games, and in 1963 he led the AL with 7 shutouts.
After the 1964 season (and 2 weeks before his 35th birthday) Herbert was traded to the Phillies for youngsters Danny Cater and Lee Elia. He spent his final 2 seasons in Philadelphia, making 19 starts in 1965, but appearing primarily in relief in 1966.
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