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Buddy Bailey, One of MiLB’s Winningest Managers, Dies at 68

Tigres de Aragua announced his death after a 36-season career highlighted by six Venezuelan titles, a 2009 Caribbean Series crown, plus roughly 2,400 minor-league wins.

WASHINGTON, DC - JUNE 04: A view of a Chicago Cubs baseball cap on the stairs of the dugout during the game against the Washington Nationals at Nationals Park on June 04, 2025 in Washington, DC. (Photo by G Fiume/Getty Images)
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Overview

  • Venezuela’s Tigres de Aragua confirmed Bailey’s death on Tuesday; he was 68.
  • His Minor League managerial career spanned about 36 seasons across the Braves, Red Sox and Cubs organizations.
  • Reports cite 2,417 to 2,419 regular-season victories, placing him fourth or third all-time on MiLB managerial wins lists depending on the tally.
  • He became a towering figure in Venezuelan winter ball, leading Tigres de Aragua to six LVBP championships and the 2009 Caribbean Series title.
  • He guided the Myrtle Beach Pelicans to the 2016 Carolina League crown, logged 490 wins with the club, left after 2024 as MiLB’s winningest active manager, and drew tributes from former players including Adbert Alzolay.