3 moves the Cubs must make before the New Year to save the offseason

As expected, it's been a rather quiet first half of the offseason for the Chicago Cubs. They've made some key moves as part of an ongoing rebuild within their bullpen, but they have yet to add a single major-league player to either the lineup or rotation.

With Kyle Tucker still mulling over $300+ million offers and non-roster invitee Scott Kingery currently representing the biggest upgrade on the bench, that has to change, and fast.

With the Winter Meetings well in the rearview mirror, the Cubs are staring down a tight deadline to reshape the roster between now and the beginning of spring training. What can they do before 2025 is out to put themselves in an advantageous position heading into 2026?

3 moves the Cubs must make before the New Year to save the offseason

Sign free-agent pitcher Michael King

This feels like beating a dead horse at this point, as the fit between the Cubs and King has been clear from the outset of the offseason.

Though injuries diminished his effectiveness in 2025, the 30-year-old successfully completed his transition from the bullpen to the rotation in 2024, pitching to a 2.95 ERA and 3.33 FIP in 173 2/3 innings while accruing 3.9 fWAR. His 4.42 FIP from this year was more unsightly, but he's got the talent to at least help front a rotation.

With recent rumors suggesting King may be out of the Cubs' price range, let this serve as a reminder that the team needs a pitcher of his caliber this offseason. Matthew Boyd, Cade Horton, Shota Imanaga, and Jameson Taillon are a fine foundation, but that group was lacking a clear and obvious impact in the playoffs.

A union with King — plus a healthy return from Justin Steele — would do wonders for the status of the North Siders' rotation.

Add another left-handed reliever to the bullpen

The signings of Hoby Milner and Caleb Thielbar give the Cubs some plausible deniability on this front, as both southpaws are more than effective at silencing left-handed batters when called upon.

Still, neither profile particularly well as a high-leverage set-up guy — Milner ran a 19.8% strikeout rate this past season, and Thielbar is a 38-year-old who is significantly worse against righties. Unless the team expects Luke Little or Jordan Wicks to magically make that leap in 2026, there's room to add another left-handed reliever who can pitch in the eighth inning.

There aren't many free agents left who fit the bill, but a trade for Adrian Morejon or Wandy Peralta of the Padres could make sense for both sides, particularly if A.J. Preller is as keen on a blockbuster trade as the rumors suggest.

Trade one of next year's many free agents for a controllable bat

This one isn't quite as pressing as the other two agenda items, but it's clear the Cubs have backed themselves into a corner next offseason.

Carson Kelly, Nico Hoerner, Ian Happ, Seiya Suzuki, Jameson Taillon, and Matthew Boyd (mutual option) are all set to hit free agency following the conclusion of the 2026 MLB season. That's a huge percentage of the team's core on both sides of the ball, and it gives the front office a clear ultimatum to act upon.

Trading (for instance) Happ doesn't help the offense unless the team brings back a bat in a trade (or uses the financial savings to sign a free agent), but it may bring in some controllable talent for a team that is severely lacking in that department right now.

It's not unreasonable for the Cubs to go all-in on this core in 2026 and let the year play out... but the team isn't doing that. They've just signed a trio of relievers to low-risk deals. If that's "going all-in", then Cubs fans should be prepared for another long championship-less streak.

It's time for the front office to pick a lane. If that means having to trade one of the roster's longest-tenured members, then so be it.