Legendary Cubs minor league skipper Buddy Bailey passes away at 68

Photo courtesy: SB Cubs

Dustin Riese · Senior Writer · 10 hours ago

Things haven't been great for the Chicago Cubs in terms of their play over the past week, and things only got tougher for the organization on Tuesday night. In case you missed it, we regret to inform you that former South Bend and Myrtle Beach Pelicans manager Buddy Bailey has passed away at the age of 68.

One of the more beloved managers to ever manage on the minor league circuit, Bailey played a massive role in the Cubs' Minor League success up until he retired after the 2024 season. Bailey spent seven seasons with the Pelicans until his retirement.

He was the winningest active manager at the time and was the third most successful manager in Minor League history, with more than 2,600 wins. That puts him in a class of his own, as he is just one of 11 Minor League Managers to secure 2,000 or more wins over a 35-year coaching career.

While he may be known for his most recent success with the Pelicans, Bailey has spent the majority of his managerial career in the Cubs system, accumulating 20 years of experience with the organization. That included stops with all four of the Cubs' current full-season squads and even spent time in Daytona when the Cubs owned the Daytona Cubs in the early 2000s.

Before his time with the Cubs, Bailey was part of the Red Sox and Atlanta Braves organizations, and his success is recognized throughout the country. He also had experience managing Venezuelan Winter League clubs, demonstrating that he is more than just an average Minor League Manager.

The mark Bailey left not only on the Cubs organization, but everywhere he coached is going to be felt as the consensus was always the same about him. From all accounts, he was not only a genuine human being who cared about his players but also someone who would always sacrifice everything to see his players achieve the success they deserved. That is a rare trait in today's game, and it's very clear that players gravitated toward him based on how he conducted his business.

“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.”

Current Cubs outfielder Kevin Alcantara enjoyed some time with Bailey in Myrtle Beach and had this to say about his experience with Bailey. “He was a very caring person, a hard-working person,” Cubs outfielder Kevin Alcántara said, per Marquee. “I hope his soul is at peace because he was a good person with me, with guys. He loved extra work. Honestly, he put people in a good place. For those reasons, many guys who passed through there are here now.”

The second part of his quote is the key takeaway, as Bailey would work more hours than expected to put players in the best position possible. Alcantara was one of those players, and his time with Bailey helped him grow into one of the Cubs' top prospects over the past few seasons.

When you examine his track record with the Cubs and their entire organization, he won the Midwest League Championship with the Cubs in 2019 before leading the Pelicans to several playoff appearances from 2021 to 2023. He was also the last manager the Iowa Cubs had prior to Mark Peavey arriving, posting a 78-66 mark in 2007.

He certainly falls into the category of 'they don't make them like they used to,' and the entire Cubs organization, as well as the Baseball world, will greatly miss him. Our thoughts and prayers are with the Bailey family during this difficult time, as the entire Cubs organization stands with you in your time of grief.