The Cubs don’t need to tear anything down, but they do have a real chance to get younger this winter.
That matters because Chicago just finished as MLB’s second-oldest team in 2026, with an average age of 30.1. Only the Los Angeles Dodgers were older at 30.4.
The Atlanta Braves and Philadelphia Phillies also checked in at 30.0, and all four clubs made the playoffs. Age, at least in this group, did not keep anyone home in October.
Still, the Cubs are staring at an offseason that could reshape the roster in a meaningful way. Jed Hoyer has several aging pieces heading toward free agency once the World Series ends, and most of them are pitchers - the area the front office is expected to attack this winter.
That list includes Caleb Thielbar, who is 39, as well as Shota Imanaga at 33, Matthew Boyd at 35, Kevin Gausman at 35, Clay Holmes at 33, Colin Rea at 36, Michael Conforto at 36, Trent Thornton at 33 and Tyler Austin at 35.
The upside for Chicago is obvious: this isn’t about stripping the roster down. It’s about using the chance in front of them to replace some of those mid-30s innings and get a little more sustainability on the mound. The Cubs had a pitching staff that couldn’t stay healthy and, at times, looked like it was being managed one day at a time.
That said, veteran presence still has value, and this front office isn’t in a place where it should simply trust unproven players to carry the load. The Cubs are in the middle of a contention window, not some full-scale reset.
That’s also why the discussion around replacing Ian Happ and Seiya Suzuki keeps coming up. Both are entering their age-33 seasons in 2027, and the idea of handing those corner spots over to Pedro Ramirez and Matt Shaw does not sound like the cleanest solution. Unless one of them returns, the odds still point to another veteran joining the mix.
So the task for Hoyer isn’t to chase youth for youth’s sake. It’s to take advantage of a rare opening to freshen up a roster that has too many older pieces and make the team a little more dynamic heading into next season. If Chicago lets that chance slip by, it would feel like a missed opportunity.
In Other News...
Cubs Suddenly Have A Compelling New Outfield Option To Watch
With the Guardians out of the ALCS, the offseason chatter around Steven Kwan can finally take on a more practical shape for clubs that need outfield help, including the Cubs. Kwan is headed into his final year of arbitration, which naturally makes him a player teams around the league will monitor closely, especially ones trying to reshape the edges of a roster and keep the lineup balanced.
For Chicago, the interest makes sense on paper. The Cubs have been linked to the need for outfield reinforcements with some departures looming, and Kwan fits the kind of dependable, contact-oriented profile that can stabilize a lineup. Whether Cleveland actually decides to move him is another matter, but the possibility gives the Cubs a new name worth watching as the winter market begins to take shape. [Read more 🡒]
Former Cubs Coach Drawing Interest As Mets Rework Their Staff
The Mets are still sorting out the shape of their hitting staff, and a familiar name for Cubs fans has surfaced in the process. Kevin Long and former Cubs coach John Mallee are among the candidates being interviewed for a hitting coach role, as New York looks to reshape a group that already has Troy Snitker and Rafael Fernandez expected back.
Jeff Albert, the clubs director of hitting, is not expected to return, which leaves the Mets deciding how they want the next layer of the staff to look. They have not settled on whether to bring in a new director of hitting above Snitker or simply add another assistant hitting coach beneath him, leaving Mallees fit in that structure as part of the ongoing review. [Read more 🡒]
Cubs Front Office Suddenly Has An Unexpected Seattle Concern
The Mariners managerial search has taken an unexpected turn for the Cubs, with Chicago director of player development Jason Kanzler emerging as one of the names under consideration in Seattle. The job opened after the Mariners decided not to retain Dan Wilson following the 2026 season, and Kanzler is now being weighed alongside former Astros manager Joe Espada and Dodgers special assistant Rocco Baldelli.
For Chicago, the interest is notable because Kanzler has coaching experience in the majors, but not nearly the same managerial background as some of the other candidates. If Seattle decides he is the right fit, the Cubs would suddenly have a front-office issue to sort through, since Kanzler sits in a key spot within their player-development operation and his departure would force some internal reshuffling. [Read more 🡒]