SOUTH BEND, Ind. (WSBT) — Buddy Bailey, the South Bend Cubs manager who led the Cubs to their first Midwest League championship as a member of the Chicago organization in 2019, passed away on Tuesday at 68, the team announced.
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 managers ever to have 2,400 or more wins.
“Buddy meant so much to us, not just as part of our organization, but as fans of baseball,” South Bend Cubs Chairman and Owner Andrew Berlin said in a press release. “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 was a manager in the Chicago Cubs organization from 2005-2024, first with Daytona (then the High-A affiliate). He would touch all levels of the organization, spending time with Iowa, Daytona (again), Tennessee, Myrtle Beach, South Bend, and back to Myrtle Beach, where he retired from coaching in 2024.