Former Cubs manager David Ross faces another offseason of being overlooked

There's a very narrow path for David Ross to find his way back to a big-league managerial job this winter after the Philadelphia Phillies retained Don Mattingly, signing him to a two-year deal through 2028 as they look to pry their rapidly-closing window open just a bit longer.

The former Chicago Cubs manager, who was unceremoniously shown the door when Jed Hoyer jumped at the chance to bring in Craig Counsell in Nov. 2023, has not coached or managed since, instead working as an MLB analyst for ESPN in recent years. His best shot appears to be in Seattle, which parted ways with Dan Wilson at the end of the season and is rumored to want to replace him with an experienced manager.

It's hard to not think Ross would be in a tier of candidate below someone like Joe Espada, who was shown the door after the Houston Astros were swept by the Chicago White Sox in the AL Wild Card Series. He's had a deeply flawed roster for years and the general consensus is that his managerial prospects remain bright even after being dismissed.

Every name on that list, including Espada, Rocco Baldelli and former Cubs bench coach and Orioles manager Brandon Hyde, have managed in MLB more recently than Ross. After an incredible 2025 that saw the team come within one win of the American League pennant, 2026 was a huge step back, so the expectation for whoever is hired is to get things back on track immediately.

Is it over before it really began for former Cubs manager David Ross?

Ross had a chance to join Aaron Boone's coaching staff after being fired by the Cubs but declined the offer and has now been out of the dugout for three full seasons. There has been plenty of MLB managerial turnover during that time, but he's only been loosely connected to any of those jobs, at least publicly.

Ross was Hoyer's handpicked successor to Joe Maddon after the Cubs parted ways with the quirky skipper that led the team to a title in 2016. He managed Chicago for four years, compiling a regular-season record of 262-284. The Cubs won the NL Central in the shortened 2020 season, but were swept by the Marlins in the first round of the playoffs and never reached the postseason again during his tenure.

His final year was capped by a painful September collapse that cost the Cubs a postseason ticket and, barring a change either in how the industry perceives him or what opportunities he's open to, I can't help but wonder if we've seen the last of Rossy in the dugout.

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