No. 7: Billy Martin (556 wins)
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Martin, a former second baseman whose No. 1 was retired by the Yankees in 1986 and whose feuds with Boss George and Reggie Jackson are the stuff of legend, managed the Yankees five different times -- from 1975 to 1978, 1979, 1983, 1985 and 1988. He died in a car crash on Christmas Day 1989.