Buddy Bailey, one of the Minor League's all-time winningest managers and most enduring figures, has died. His death was announced on Tuesday by Venezuelan Professional Baseball's Tigres de Aragua, whom Bailey managed to six winter ball championships. He was 68.
Bailey amassed 2,417 regular-season victories over a Minor League managerial career that spanned 11 cities, three organizations and nearly four decades. In 2017, he crossed the 2,000-win mark with High-A Myrtle Beach, a milestone reached by only 13 MiLB managers. Under his leadership, the Myrtle Beach Pelicans won the Carolina League championship in 2016, and he was the Minors’ winningest active skipper at the time of his final game with the club, which he shepherded through the 2024 season. He ranks fourth all-time on the MiLB managerial wins list.
"His presence was super specific," Cubs outfielder Pete Crow-Armstrong, who played for Bailey with Myrtle Beach in 2022, told MLB.com's Jordan Bastian. "I think there were a lot of guys who may have been intimidated by Buddy Bailey and by his [old school] style of coaching. But sometimes that’s the perfect way to go about things.
"I think he was super impactful on me, only because I don’t think he ever made me feel like I had earned what I was getting. And I think that was so big for me. ... Buddy Bailey was incredible."
Bailey presided over many playoff appearances and division titles during his time managing in the Braves (1983-90), Red Sox (1991-2004) and Cubs’ (2006-24) systems, accumulating a .521 winning percentage (2,417-2,220) over 36 seasons. He also found outsized success managing winter league ball in Venezuela, where he turned the middling Tigres franchise into one of the most dominant dynasties in league history, leading the club to six LVBP titles and more than 500 wins. In 2009, Bailey managed the franchise to its first Caribbean Series championship, cementing his legacy in the country’s baseball lore.
Born Welby Sheldon Bailey in Norristown, Pa., Bailey was drafted by the Braves in 1979 and played four seasons in their system as a light-hitting catcher, reaching as high as Double-A. Bailey’s playing career was modest but formative, opening the path for him to leave an indelible imprint on the game through the players he mentored and communities he served. He moved into coaching in 1983 with the rookie-level Pulaski Braves, managing in the system through the end of the decade. He then spent the next 14 seasons in the Red Sox system, serving not only as a manager but in roles like advance scout, Minor League catching instructor, and field coordinator. Bailey spent the 2000 season as Boston’s big league bench coach -- his only in the Majors.
Bailey was twice named International League Manager of the Year (1996, 2003) he is one of only four skippers to win that award twice -- and named the LVPG’s Manager of the Year in 2006-07.
"You’re not going to get better at anything unless you put in the effort, the time, the reps and the work,” Bailey said in a 2024 interview, as part of a retrospective of his career produced by the Pelicans. “Everybody thinks the competition is every day, winning or losing the game. The competition is trying to find a way to tap the players, to help them push themselves to get the most out of themselves.”