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Kevin CummingsHe was definitely one of the better pitchers of his era and one of my three top 19th century pitching favorites for inclusion in the Hall (Jim McCormick and Gus Weyhing being the other two), but he didn't win 300 games.
Check it out: http://www.baseball-reference.com/m/mullato01.shtml
He probably would have easily won 300 games had he not been suspended by the American Association in 1885 for all his contract jumping violations.