His career 237-146 record and his "Sly old fox" reputation made him an important pitcher between 1891-1907 and a regular in Cap Anson's 3-man rotation in Chicago. His friendship with Ban Johnson and his influence with the players of the time positioned him to be instrumental in the early success of the American League. He is credited with persuading 39 NL players to jump to the new league for its inaugural 1901 season. He was the first manager of the New York Highlanders and when that didn't work out, he became the manager and eventually owner of the Washington Americans.
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