Between the 1882 and 1956 seasons, Ken Heintzelman, Steve Swetonic and Harry Staley were tied for the most wins for the Pirates when winning <59 games and winning <38 games, with 37 wins.

most games won pirates pitcher 1882 to 1956 and wins less than 59 and wins less than 38
Interpreted as:
most games won in the regular season pirates pitcher 1882 to 1956 and wins less than 59 and wins less than 38

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