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This guy had the number 4 retired for the Sox for his player/manager prowess, and he's one of the best player-managers ever. Known more for the latter, he was actually quite the underrated player, finishing his career with a .301/.390/.468/.857 slash, nearly 2300 hits, and 170 homers. He's also the winningest manager in Red Sox history with 1071 wins. Sadly, those only equated to one pennant and now world series wins, but hey, he was a hell of a player and manager nonetheless. #4 Joe Cronin
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