Cubs face sweeping offseason overhaul with pitching staff at the center of it all

What happened

The Cubs are staring down one of the more consequential offseasons in recent franchise memory. Per a detailed offseason outlook published by Anthony Franco at MLB Trade Rumors, Chicago carries $483MM in total future commitments — not including future deferrals, and assuming Clay Holmes opts out of his $12MM player option — while simultaneously facing a free-agent class that includes some of the most recognizable names on the roster. The position player core is, per Franco's framing, arguably the best in baseball. The pitching staff is a different conversation entirely.

Why it matters

Few teams are likely to experience as much roster turnover this offseason as the Cubs, per MLB Trade Rumors. Chicago reached the playoffs in consecutive years but did not advance beyond the Division Series in either run. Franco notes that both the pitching staff and the offense share responsibility for this year's Wild Card Series loss in San Diego, but it is the absence of impact arms that the outlet identifies as the gap separating the Cubs from the sport's top tier.

That framing lands with some weight given what the Cubs already have locked in on the position player side. Alex Bregman is under contract through 2030 at $140MM. Nico Hoerner is guaranteed $138.5MM through 2032. Pete Crow-Armstrong is locked in at $110MM through 2032. Dansby Swanson carries $78MM through 2029. That is a formidable infield and outfield foundation — and it makes the pitching question feel less like a luxury and more like an obligation.

The Cubs' identification of the rotation as their primary offseason priority, reported earlier this week, is consistent with the structural picture Franco lays out. The offense is not the problem. The arms are.

The numbers

The Cubs finished 89-73 (.549), landing second in the NL Central and 14 games back in the division race, which was already decided. Their Wild Card standing came in at rank 2, sitting +1.0 relative to the cut line — enough to get in, not enough to go deep.

The $483MM in total future commitments is the headline figure, and it comes with the asterisk that it excludes future deferrals and assumes Holmes opts out. The 2027 guaranteed payroll alone sits at $108.25MM under those same assumptions, with $10MM of Bregman's salary deferred. Phil Maton is owed $9MM through 2027, including the buyout of a mutual option on a subsequent season. Shelby Miller carries $1.5MM through 2027, including the buyout of a club option on a subsequent season.

On the arbitration side, MLBTR contributor Matt Swartz projects Justin Steele at $6.8MM, Michael Busch at $5.4MM, Edward Cabrera at $4.8MM, Javier Assad at $2.3MM, Miguel Amaya at $1.7MM, Braxton Garrett at $1.6MM, Ben Brown at $1.3MM, Gabriel Arias at $1.3MM, Daniel Palencia at $1.2MM, Ryan Rolison at $1.1MM, and Ethan Roberts at $800K. Franco flags Garrett, Arias, and Roberts as non-tender candidates.

Where the club stands

At 89-73, the Cubs closed the regular season second in the NL Central and entered the postseason as a Wild Card team. They are eliminated from the division race. The streak entering this stretch reads W1. The postseason run ended in San Diego, and the offseason machinery is now fully in motion.

What we don't know yet

### Will Holmes opt out — and what does that mean for the bullpen?

Holmes holds a $12MM player option, and per MLB Trade Rumors, he is reportedly expected to opt out. That expectation is not a club announcement, and the decision has not been reported as finalized. If he does opt out, he joins a free-agent list that already includes Shota Imanaga, Seiya Suzuki, Ian Happ, Kevin Gausman, Matthew Boyd, David Peterson, Michael Conforto, Caleb Thielbar, Tyrone Taylor, Trent Thornton, Aaron Civale, Hunter Harvey, and Tyler Austin. That is a substantial number of players whose 2027 status remains unresolved.

Several option decisions also hang in the balance. The Cubs hold a $7.5MM option on Colin Rea (with a $1MM buyout), a $2.5MM option on Jacob Webb, and a $3.3MM option on Javier Assad — though Franco notes Assad remains arbitration-eligible even if the option is declined. Matthew Boyd and the Cubs hold a $15MM mutual option with a $2MM buyout. Hunter Harvey and the Cubs hold an $8MM mutual option with a $1MM buyout. Carson Kelly and the Cubs hold a $7.5MM mutual option with a $1.5MM buyout. Caleb Thielbar and the Cubs hold a $6MM mutual option with a $500K buyout.

The Harvey decision carries its own context. Per Posterior Wire reporting from earlier this week, Harvey was largely unavailable due to injury in 2026, pitching in only 4 games for the Cubs after a history of recurring injuries. Whether the Cubs exercise an $8MM mutual option on a reliever who appeared in 4 games is a question the front office will need to answer with full knowledge of his medical picture — none of which has been reported.

The Imanaga and Suzuki situations are perhaps the most operationally significant unknowns. Both are listed as free agents, and neither departure nor return has been reported as likely or unlikely. Their presence or absence would reshape the lineup and the payroll picture in ways that ripple into how aggressively the Cubs can pursue rotation help.

What to watch

The rotation is the story. Franco's piece is explicit: the Cubs are a tier or two below the best teams in baseball because of pitching, not hitting. The Fielding Bible Awards the organization received this week — Player of the Year and Team of the Year honors for 2026 — underscore how well-constructed the defensive and positional side of the roster already is. The gap is on the mound.

Watch the option decisions first, since they set the payroll floor and clarify which returning arms are actually in the picture. The Holmes opt-out expectation, if it materializes, removes a key bullpen piece and adds urgency to the relief market as well. The non-tender decisions on Garrett, Arias, and Roberts will signal how the front office is thinking about roster construction at the margins.

And then there is the larger free-agent market, where the Cubs will presumably be active shoppers for starting pitching. The $483MM reportedly already committed is a real number, but the 2027 guaranteed figure of $108.25MM — again, under the Holmes opt-out assumption — leaves room to maneuver depending on how the option decisions fall and what the club decides to do with its arbitration class.

The position player core is set. The Cubs know what they have there, and so does everyone else. What happens this winter on the pitching side will determine whether the next postseason run ends in the Wild Card round again or goes somewhere further.

Per MLB Trade Rumors, the Cubs have the offensive foundation. The offseason is about finding out whether they can build a staff worthy of it.