Cubs rumored to suffer their first offseason loss months before the winter

The Chicago Cubs sit at the top of the National League Central division, and while that can directly be tied to the breakout season of Pete Crow-Armstrong, there is something to be said for the continuity that Craig Counsell has on his coaching staff.

While there were notable changes to the Cubs' base coaches, Counsell is in the middle of his second season with Ryan Flaherty as his bench coach. Flaherty, a former Cubs' farmhand, earned his reputation as a Major League Baseball player with the Baltimore Orioles. After his playing career, Flaherty began his coaching career with the San Diego Padres before being poached by Counsell prior to the 2024 season.

Much like his playing career, Flaherty's coaching career could see a move from the Cubs to the Orioles. Bob Nightengale of USA Today reports that Flaherty will be a candidate for the Orioles' managerial opening this offseason, assuming there is a search.

"If the Orioles change managers again in the offseason, the leading candidate will be Cubs bench coach Ryan Flaherty, who played six years for the Orioles and nearly landed the Padres’ manager gig two years ago," Nightengale reported in his Sunday notebook.

Cubs' coaching staff could see dramatic change in the offseason.

In a full-circle moment, if Flaherty were to get the job, he would be the permanent replacement to Brandon Hyde, the former Cubs' bench coach who had been the Orioles' manager since 2019. After a horrific start to the 2025 season, Hyde was cast as the scapegoat for the negligence of Baltimore's ownership group. Tony Mansolino is serving as the Orioles' interim manager.

If Flaherty were to leave, it would be interesting to see Counsell's pivot with his coaching staff. Sure, there will likely be connections from his days as the Milwaukee Brewers' manager, or, like Flaherty, he could choose to target an ascending coaching candidate who has aspirations of being a Major League manager.