Recent Offseasons Point To A Potential Big Cubs Move

It could be a rather aggressive offseason for the Chicago Cubs. 

Fresh off a disappointing postseason appearance, president of baseball operations Jed Hoyer knows this roster needs more work to compete for a World Series. Hoyer tried to be aggressive at the trade deadline by trading for Kevin Gausman, Clay Holmes, Tyrone Taylor, and Ryan Zerferjahn, but those moves didn’t help. 

Now the Cubs face plenty of question marks. The biggest is what the team will do to upgrade its rotation before the start of the 2027 season. With four of their current starters set to hit free agency, Chicago will be looking extra hard for some starting pitching help in the offseason. 

Gausman and Shota Imanaga are free agents, while both Matthew Boyd (mutual option) and Holmes (player option) will likely decline their options to test the open market. Those four pitchers could all leave in free agency. 

That could lead the Cubs to make a big move for a starting pitcher. They will obviously be aggressive in free agency to land at least one starter and upgrade this group. But don’t be surprised if the front office tries to make a big trade for a starter. 

The Cubs did exactly that last offseason, trading their No. 1 prospect Owen Caissie for Edward Cabrera. While that trade didn’t really work out for the team in 2026, it signals that the front office isn’t afraid to trade younger players for a potential star with upside. 

The same thing happened the offseason before, when Chicago traded Hayden Wesneski, Isaac Paredes, and Cam Smith for superstar Kyle Tucker. That turned out to be a disappointing trade for the Cubs, but it doesn’t change the fact that the front office made a big move to go all in. 

The Cubs desperately need some pitching help and could make another big trade this coming offseason. They could potentially make a move for one of the Mariners starting pitchers. There were rumors circulating around the deadline that Emerson Hancock and George Kirby might have been available. 

There’s also a chance that the Yankees could trade away Ryan Weathers or even Luis Gil, both of whom could be ideal targets for the North Siders. 

The Cubs will likely be trying to make a big move this offseason to improve their roster. If they have their eyes set on a pitcher who has multiple years of control, expect Matt Shaw or Pedro Ramirez to be a part of that deal.