Jed Hoyer’s offseason to-do list starts with one obvious problem: the Cubs need pitching, and they need a lot of it.
The rotation and bullpen both have holes that can’t be papered over with wishful thinking. After injuries and uneven performances undercut the staff this season, Chicago is headed into the winter looking at a rotation that includes Edward Cabrera, Javier Assad and Braxton Garrett, plus two arms carrying real question marks in Justin Steele and Ben Brown. Steele and Brown have top-end ability, but injuries have shaped their recent stories far too much.
The bullpen hasn’t exactly inspired confidence either. Hoyer missed on all of his major relief additions last winter, and repeating that mistake would be a rough way to try to close the gap on the Milwaukee Brewers in the National League Central.
So the Cubs are going to scour every route possible: prospects, free agents, trades. And if Hoyer wants to dream big - or wildly - these are the kinds of names that would at least force a conversation.
Jacob deGrom is the kind of idea that lives in the “probably not happening” bucket, but the appeal is easy to see. The Rangers right-hander turned in a 3.11 FIP and struck out more than 200 batters in only 162 2/3 innings this year.
The catch, of course, is everything else: he’s 38, turns 39 next summer, and is due $37 million next season. Texas would likely love to shed at least part of that bill, and the Cubs have never been eager to dive into high-dollar, long-term pitching deals.
Still, given the age, the injury history and the salary, it would be a stunner if deGrom ended up being the answer at the top of Chicago’s rotation.
Sandy Alcantara makes a little more sense on paper, even if the Marlins probably aren’t eager to move him. Miami has a $21 million club option for next year that it will almost certainly exercise, and Alcantara has been the subject of trade chatter for years without actually leaving Florida.
Last season, he led the league in starts and innings pitched, but the stat line wasn’t spotless: he posted a 4.08 FIP and allowed an MLB-high 204 hits. He still hasn’t fully looked like himself after Tommy John surgery wiped out the 2024 season, though the upside remains obvious.
The Cubs and Marlins have already done plenty of business talks in recent years, including the Edward Cabrera trade last winter, so the familiarity is there. A move before the deadline, though, would still be a surprise.
If you want to push the needle even further into fantasy territory, Spencer Strider belongs on the list. The Braves right-hander makes $22 million in each of the next two seasons, with a club option for the same amount in 2029.
Since he won 20 games and finished fourth in NL Cy Young voting in 2023, injuries have kept piling up, and even when he’s been available, he hasn’t been the same pitcher. Since the start of the 2024 season, he’s made just 33 starts and put up a 4.74 FIP and 1.402 WHIP.
That’s a massive amount of risk for Chicago, with at least $44 million still owed. But if Atlanta is willing to eat money or settle for a smaller return, that’s the sort of circumstance that can at least put a name like Strider into the mix.
Then there’s Mason Miller, who might be the most extreme swing of the bunch. Compared with him, Strider almost feels tame.
The Padres closer is just entering arbitration, which means three years of team control, and he won’t turn 29 until next August. He also just delivered a dominant season, making 66 appearances and finishing with a 1.67 ERA while striking out 129 hitters in 70 innings.
Trading for him would be the kind of move that could wipe out a farm system in a hurry. That’s the price for one of the most overpowering arms on the market, and it would take a heavy lift to pry him away from San Diego.
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 🡒]