The Cubs are heading into an offseason that could move fast the moment the World Series ends.
With the 2026 season in the books, Chicago and Jed Hoyer have a real evaluation ahead of them after falling short of the World Series. And this won’t feel like a normal winter.
The current CBA expires on December 1, which means November is expected to get messy in a hurry. Instead of waiting around, executives are expected to push to get deals done before the league’s rules potentially change.
That’s why the Cubs should be ready to get back on the phone with a few familiar trade partners right away. A lot of early offseason business grows out of conversations that already happened during the season, and Chicago has been down this road before. Last winter, the Cubs landed Edward Cabrera after being tied to the Miami Marlins in trade discussions for a year.
The Angels are one club Chicago ought to circle back to quickly. Reid Detmers was the one that got away at the trade deadline, and Los Angeles became a team worth watching late in the regular season after the news of Stan Kroenke purchasing the team from Arte Moreno. Assuming John Mozeliak remains in place, there’s a good chance the Cubs revisit those talks early.
Minnesota also makes sense as a team to call. Pitching is going to dominate the Cubs’ offseason, and if Hoyer isn’t interested in paying Tarik Skubal, then any top-of-the-rotation arm likely has to come via trade.
Joe Ryan, who is under team control through the 2027 season, could be a name worth pursuing if the Twins decide to cut their losses early. If anything, his value is only likely to go down if part of the regular season gets lost, which makes now the time to act.
Seattle should be back on the list as well. The Cubs were linked to the Mariners at the deadline amid rumors that George Kirby and Emerson Hancock were available.
That kind of connection doesn’t just disappear, especially with Chicago needing to replace most of its starting rotation. If the Cubs were interested before, they should be interested again.
Then there’s San Francisco. The Giants kept Logan Webb at the deadline, but that doesn’t mean teams should stop asking.
Webb is under control through 2028, and as he gets closer to free agency, the Giants may be more open to listening. Once the World Series wraps up, the Cubs should check again and see whether San Francisco’s stance has shifted.
In Other News...
Cubs Lose Another Pitching Depth Option After Brief Uneven Stint
Corbin Martin is one of six minor league players who have elected free agency after finishing the season on outright assignments, a move that lets them reach the market earlier than the usual major league free-agent timeline. For the Cubs, it means another pitching depth name is on the move after a brief, uneven stint in the organization, a familiar kind of churn at this time of year as clubs sort through the back end of the roster.
Martin had been part of a group that included players with recent designation-for-assignment history and varying minor league resumes, underscoring how quickly those depth pieces can cycle through an organization. For Chicago, the timing matters because these are the kinds of arms teams often hope to keep around as insurance, but once a player chooses free agency, the Cubs have to look elsewhere for that same low-cost rotation and bullpen cushion. [Read more 🡒]
Ian Happ Just Sounded Like A Cub Saying Goodbye
Ian Happs recent comments carried the kind of weight that gets attention in Chicago, because they sounded like a player who understands the business side of the game and what free agency can mean for a longtime Cub. He spoke with appreciation for his time in the organization while also acknowledging that his run with the team may be nearing its end, which is not usually the tone of a player headed into an offseason of uncertainty.
Happ is set to hit free agency this winter, and there has been at least some indication he could be open to a team-friendly arrangement if it keeps him on the North Side. The Cubs, for their part, have had interest in bringing him back and could envision a platoon role, which leaves just enough room for a return, even if the conversation around it already feels a little like a goodbye. [Read more 🡒]
Cubs Rotation Need Just Ran Into A Brutal Tarik Skubal Reality
The Cubs know the rotation could use another impact arm, but the market may be about to make that search a lot tougher. Tarik Skubal is expected to land at the top of the free-agent pitching class, with Jeff Passan reporting that his next deal could climb to a level that would reshape the entire market. For a Chicago team trying to balance ambition with roster-building realities, that kind of price tag immediately turns a dream fit into more of a luxury than a plan.
Chicago is not expected to seriously chase Skubal, and age is part of the reason the fit looks so difficult. Instead, the Cubs are more likely to keep working through other starting-pitcher options once free agency opens, hoping to find a deal that brings real rotation help without forcing them into the kind of bidding war that only a handful of clubs can afford. [Read more 🡒]