24. Joe Maddon
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Maddon’s inclusion might be a bit of a head-scratcher, but there are two reasons he’s worthy. No. 1: He guided a lowly Tampa Bay franchise to an AL pennant — its first winning season in franchise history. No. 2: Maddon pulled off perhaps the biggest miracle ever when he became the first manager since Frank Chance to win a World Series with the Chicago Cubs. Is that enough?