Starter's Gun: Cubs' Crucial Offseason Begins Monday Afternoon

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The Chicago Cubs have watched several key players officially become free agents over the last handful of days. None of them were surprise cases. Even though options could technically have kept Carson Kelly, Matthew Boyd and/or Clay Holmes around on their existing deals for 2027, that they would instead enter the open market was inevitable. The first real drama of the offseason comes Monday afternoon, when the Cubs not only have to decide about Colin Rea's club option for next year, but must also either extend (or elect not to extend) the qualifying offer to Seiya Suzuki, Ian Happ and/or Boyd.

As I've already laid out, the team needs to be ready to spend big this winter and head into 2027 with a massive payroll, so I believe they should extend the QO to all three of their reasonable candidates. In all likelihood, either Happ or Boyd would accept it, but that would be fine: each is a solid use of $23 million and change on a one-year deal. Rea is a spare part, and while he's valuable both for his versatility and his amiable clubhouse presence, it's not at all clear that he can be worth $6.5 million in raw on-field value next year, so the team might need to cut ties.

More important than any of those decisions, though, is what comes next, which will be a frenzy. One month from Monday, the owners will lock the players out and shut down the league for at least another couple of months. The offseason will enter a deep freeze, and whenever the lockout ends, there will be a scramble to accomplish spring training and get the season underway. Most of each team's business, therefore, needs to be done over the next four weeks. That's not how most winters work, but since it's what's happening this time, we'll see teams make a huge number of moves at a point in the offseason that's usually reserved for feeling-out processes.

This evening, we'll see which players (not just on the Cubs, but league-wide) receive the QO, clarifying the market for top talent. That will be the real starter's gun for the offseason, and the Cubs need to react to it with a burst out of the blocks. Monday also marks the end of the five-day exclusive window in which teams can negotiate only with their own players, so this deadline coincides with the real beginning of the Freddy Peralta and Tarik Skubal sweepstakes, despite the fact that neither of those hurlers are eligible to receive the QO.

Skubal, Peralta, and Michael King headline a strong class of starters who won't have the encumbrance of a QO on them as they enter free agency. Keep in mind that the Cubs, as competitive-balance tax payers in 2026 and a large-market team, get far worse compensation for their own players if they sign elsewhere after turning down the QO than they must give up if they sign a player who receives a QO this winter. For that reason, every decision to sign someone who has that attached to them (Trevor Rogers of the Orioles, for instance, is certain to receive one) will have to be weighed especially heavily, and the Cubs might be wise to get more aggressive in the pursuit of players without the QO to worry about than they otherwise would.

Be it in free agency or via trade, and be they returnees or new faces, the Cubs need to add at least two corner outfielders, a catcher, four starting pitchers and two solid relievers this offseason. Ideally, one of those position players will be a big, middle-of-the-order bat, but if they aren't, the team needs to shop for one of those, too. Their shopping list is long and the items on it are expensive. The time they have to get it all done is short. Beginning Monday, it will be an extremely active month throughout baseball. The Cubs need to start finding fits almost as soon as the QO deadline passes at 4 PM CT Monday.