Rickey Henderson
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One of the greatest baseball players of all time and the quintessential leadoff man, Henderson is baseball’s all-time leader in runs and steals. In 1998, he stole 66 bags to become the oldest player to lead baseball in steals, at 39. At 43, he became the oldest player to man centerfield. He last played in the majors at 44 in 2003, but wouldn’t officially retire until 2007.