Former South Bend Cubs Manager Buddy Bailey Passes Away at 68
MWL South Bend Cubs

Former South Bend Cubs Manager Buddy Bailey Passes Away at 68

Published on September 23, 2025 under Midwest League (MWL)
South Bend Cubs News Release


SOUTH BEND, IN - Welby Shelton Bailey, or Buddy Bailey as most people called him, had a lifelong love for the game of baseball. Over his 45-year career in baseball, Bailey would do it all, managing at every level of the Minor Leagues, winning league championships, earning Manager of the Year awards, coaching countless players who would reach the Major Leagues, and through it all, becoming the one of the winningest managers in Minor League History.

"Buddy meant so much to us, not just as part of our organization, but as fans of baseball," said South Bend Cubs Chairman and Owner Andrew Berlin. "Our first championship as a Cubs affiliate in 2019 doesn't happen without Buddy. He had a feel for the game unlike any other. On a personal level, he quickly became a friend, a storyteller, a father to the players, a brother to colleagues, and a dear man that will be missed, beyond measure."

Bailey, who is third all-time in wins by a Minor League Baseball manager with 2,419, spent one season with the South Bend Cubs in 2019. He is just one of three MiLB skippers ever to have 2,400 or more wins. Of course, that sum does not count his win total managing in Winter Baseball across Latin America for multiple decades.

Although his time at Four Winds Field was short, Bailey's single campaign in South Bend was highlighted by many momentous accomplishments, both for the team, and individually for Bailey. He led the South Bend Cubs to its first Midwest League Championship as a Chicago Cubs affiliate, sweeping the postseason with a perfect 7-0 record in three rounds over Bowling Green, Great Lakes, and Clinton. On June 6, 2019, Bailey earned career victory 2100, with a 4-1 triumph of Bowling Green. At the time, Bailey became one of eight Minor League managers ever to eclipse 2,100 wins.

The history continued in 2019 as Bailey climbed the all-time ranks. In that single season, he leapfrogged four separate spots in the top 10 of all-time MiLB victories. First, victory 2094 passed Lefty O'Doul. Then, win 2,108 moved ahead of Jack Dunn. Further, his 2,123rd win exceeded Bill Clymer. Lastly, the 2,129th win was good for seventh place all-time, passing Larry Gilbert.

The 2019 season also featured the final Midwest League All-Star Game, where Bailey skippered the East Division All-Stars to a victory over the West Division, which of course was ended with a sudden-death home run derby, following a tie game of 3-3 after nine innings. Bailey also got the chance that night to catch up with an old managing friend in the Cubs system, Ryne Sandberg. 'Ryno' threw out the first pitch before the game.

Bailey was drafted as a player twice, originally in 1978 by the Kansas City Royals in the 26th round, Bailey chose not to sign and to attend the University of Lynchburg. Following his Collegiate playing career, Bailey was selected by the Atlanta Braves in the 16th round of the 1979 MLB Draft. The Braves selection proved to be important not just for Bailey, but the history of the game.

Though he played just 119 games over four seasons a pro player, Bailey would ultimately be influenced by two Hall-of-Fame Major League managers who encouraged him to get into coaching. Bobby Cox and Joe Torre.

The Braves saw the same coaching potential. Atlanta gave Bailey his first opportunity to become a professional manager at the age of 26, in 1983 with rookie-level Pulaski in the Appalachian League.

From there, Bailey worked with the Braves until 1990, until he joined the Boston Red Sox organization. His first opportunity with Boston came in his college town, Lynchburg, in the Carolina League, managing the Hillcats in 1991 and 1992. His first Triple-A job followed shortly after in Pawtucket. Then in 2000, it was the call to the Big Leagues.

In his first and only season at the Big-League level, Bailey was asked to join manager Jimy Williams' staff at Fenway Park with the Red Sox in 2000. Williams sadly passed away in January of 2024, and when told the news in a private conversation, Bailey referenced his appreciation for Williams to accomplish his dream.

2004 would be the final year for Bailey with Boston. Following a rare season-off in 2005, his final organization would call. The Chicago Cubs.

Bailey's first Cubs assignment came with the High-A affiliate of Chicago at the time, Daytona. From there, he would touch all levels of the organization, spending time with Iowa, Daytona (again), Tennessee, Myrtle Beach, South Bend, and back to Myrtle Beach, in that order.

2,419 wins later, and a lifetime of baseball. One of the best of all time.

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