One bold Cubs trade could reshape everything before 2025 Winter Meetings

The Chicago Cubs will be in the market for a power pitcher to add to their starting rotation, and it's not exactly a new need for the team. The Cubs had a need for a strikeout starting pitcher last offseason and at the MLB trade deadline, but Jed Hoyer's front office likely has learned that waiting to strike often leads to disappointment.

Look no further than at the deadline last season. In the weeks leading up to July 31, the Cubs were rumored to be interested in some All-Star caliber names--Sandy Alcantara, Joe Ryan, and MacKenzie Gore--but came away with Michael Soroka. Even last offseason, despite Corbin Burners and Walker Buehler looking like ideal options, the Cubs wound up with Matthew Boyd.

Now, to be fair, the Cubs unlocked an All-Star campaign from Boyd while Burnes missed most of the season with Tommy John Surgery, and Buehler didn't even last season with the Boston Red Sox. However, if the Cubs truly want to address their need without the worry of having to circle back to it at next season's trade deadline, they may need to make a bold move before the 2025 Winter Meetings.

The one trade Cubs fans should watch before the 2025 Winter Meetings

The Winter Meetings are expected to take place December 8 through December 11. Expecting the Cubs to make an impact free-agent signing before then seems unlikely, but the team could strike early in the trade market.

Two things are true when it comes to the Cubs' offseason needs: It'll probably be easier for them to address their need for a starting pitcher via the trade market, and replacing Kyle Tucker's offense will likely be done through free agency.

If the Cubs were smart, they would trade for a top-of-the-rotation starting pitcher before the Winter Meetings. A team like the Miami Marlins with Alcantara and Edward Cabrera likely won't be willing to make such a defining move early in the offseason, but the opportunity for the Cubs could come with the Minnesota Twins.

The Twins started their rebuild at last season's deadline, and 2026 surely won't be a year where they can expect to contend. That should place Ryan firmly on the trade market, and that is the move the Cubs should try to get done as soon as possible.

A career strikeout rate of 27.6%, Ryan is the exact pitcher that the Cubs are looking for. Not to mention, Ryan is under team control for two more seasons. If the Cubs are willing to move someone from the group of Owen Caissie, Mosies Ballesteros, Jefferson Rojas, and Kevin Alcantara, there figures to be a match with the Twins and for a pitcher under control beyond 2026.