Orioles and Padres Interested in Cubs Bench Coach Ryan Flaherty

The Chicago Cubs might be on the verge of losing one of their most important voices in the dugout this offseason.

Bench coach Ryan Flaherty, Craig Counsell’s right-hand man, has emerged as the betting favorite on BetOnline.ag to become the next manager of the Baltimore Orioles — a franchise Cubs fans already have some history with.

It’s déjà vu on the North Side. Back in December 2018, Brandon Hyde was hired away from the Cubs’ staff to take over in Baltimore. He lasted seven seasons and reached the postseason in back-to-back years, highlighted by a 101-win campaign in 2023. But after the Orioles failed to win a single playoff game and stumbled out of the gates in 2025, Hyde was let go — reopening a familiar lane between Wrigley and Camden Yards.

Now, once again, the Orioles are circling a Cubs bench coach.

And this time, the fit is obvious.

Flaherty spent six seasons in Baltimore as a versatile infielder, well-respected in that clubhouse, loved by that fanbase. Once his playing days ended, he jumped straight into the Padres’ front office and development system, eventually rising to bench coach in San Diego before the Cubs hired him to join Counsell’s staff ahead of the 2024 season.

Around the league, Flaherty already carries the label of a “future manager.” He had that reputation in San Diego, where front office voices openly hinted he was being groomed for more responsibility. And inside the Cubs clubhouse, he’s viewed as the quiet strategist — the guy who sits in every game-planning meeting and helps translate the front office data into something usable between the lines. That’s the modern managerial archetype, and Flaherty fits it cleanly, which is why his name keeps coming up.

And it’s not just Baltimore calling.

Padres Vacancy Could Be a Perfect Fit

The Padres also have a managerial vacancy after Mike Shildt’s surprising retirement, and Flaherty is expected to be in that mix as well.

The noise is getting louder — and the more his name pops up, the less likely it feels that the Cubs will retain him in 2026.

Flaherty is more than just a bench coach. He’s a key strategist, a trusted sounding board for Counsell, and an influential voice in everything the Cubs do from prep work to late-game decision-making. Losing him would be a real hit to the staff.

But that’s the cost of success. When you’re a well-run, competitive organization, other teams start circling. They want what you’ve built.

And right now, they want Ryan Flaherty.