Chicago Cubs 2025-2026 Offseason Wish List

Bring In a Big Rotation Arm

The Cubs’ starters played arguably the biggest role in keeping the team afloat in the second half, and they nearly led the way to an NLCS berth with the way they performed in the early postseason rounds.

Still, there’s a pretty clear need to find a way to improve the rotation. Just take a look at what they have returning next season:

• Cade Horton is fresh off being named the runner-up in NL Rookie of the Year voting, but he’s still early on in his big-league career. While his future is very bright, it’s not unreasonable to expect more challenges in his sophomore year

• Matthew Boyd earned his first All-Star nod last summer and was the most consistent arm in the rotation. However, he faced some struggles down the stretch, he’ll turn 35 in February, and he’s entering potentially the last year of his deal (mutual options for 2027).

• Jameson Taillon provided quality innings when he was healthy, but he did miss about two months of action due to lower-body injuries. He’s also entering the last year of his deal, and he just turned 34.

• Shota Imanage accepted the Cubs’ qualifying offer last month (one year for $22.025 million), and he is a one-time All-Star with top-five finishes in NL Cy Young and Rookie of the Year voting in 2024. However, he himself struggled in the second half and into the postseason, to the point that he didn’t even pitch in Game 5 of the NLDS (which was supposed to be his day to pitch).

• Colin Rea spent a lot more time in the rotation than likely was ideal entering the year, but he pitched admirably and helped stabilize things as the injury bug hit. Still, he’s 35 years old and might fit best as a swingman.

• Justin Steele finished fifth in NL Cy Young voting in 2023 and had turned into one of the better starters in the league over the last few seasons. However, he underwent a “revision repair” of his left UCL, and it’s unclear exactly when he might be ready to pitch.

• Javier Assad, Jordan Wicks and Ben Brown provide depth, but injury (Assad) and underperformance (Wicks, Brown) kept them from being key contributors in 2025.

It’s a solid group of starters with enough depth to cover for injuries or underperformance, but it doesn’t feel, on paper, like the most intimidating group. It seems to be missing that upper-tier arm. So where can the Cubs look to find one?

As far as free agency goes, Dylan Cease (a former prospect in their system) is already off the board after signing with the Toronto Blue Jays. Other top free-agent starter options include Framber Valdez, Ranger Suárez, Michael King and Zac Gallen. Each are already at least 30 years old, but each also has the potential to provide high-end production.

Another intriguing free-agent possibility is Tatsuya Imai, the 27-year-old Japanese right-hander. Chicago reportedly has “very real” interest in Imai, who has until January 2 to sign with an MLB team.

Though it’s unclear what kind of contract it will take to land, and though there seems to be some question regarding if he’d be more than a mid-rotation arm, he could still be a very good add (with upside) to the Cubs rotation.

The trade market is another avenue Chicago could pursue. At this past trade deadline, upper-tier starters with multiple years of control — such as Minnesota’s Joe Ryan, Miami’s Edward Cabrera and Washington’s Mackenzie Gore — weren’t moved. The Cubs would certainly have to dip into their prospect capital to get a deal done, but they should look at this side of the market for an upgrade.

All in all, a frontline starter (or close to it) feels like a must. Chicago should have plenty of avenues to explore to try to acquire one.

Bolster the Bullpen

Unlike in the rotation, at this point, the Cubs’ bullpen has a much different outlook moving into next season.

Daniel Palencia, who took hold of the closer’s role from essentially mid-May on, will return and likely slot into a late-inning role again. Phil Maton, who Chicago signed to a two-year, $14.5 million deal at the end of November, has made at least 63 appearances every season since 2021 and should provide consistent innings. Porter Hodge will also look to rebound for a season more in line with his impressive rookie campaign in 2024.

Outside of that, though, things currently look different. Gone are key contributors like Brad Keller, Caleb Thielbar and Drew Pomeranz. At the moment, less-proven internal options like Luke Little and Ethan Roberts would be in line to take their place. Depending on the starting pitching outlook, arms like Rea, Assad or Brown could move into the bullpen full time until a need arises in the rotation.

Regardless, more relief additions are clearly necessary.

Reunions with Keller, Thielbar or Pomeranz aren’t out of the question, though it’s unclear how their 2025 success will impact their market. The Cubs could go after a top-tier reliever still on the market, like Edwin Díaz or Robert Suárez, but they’ve been mostly hesitant to go big for relief arms.

It’s more likely that Chicago rebuilds the bullpen with more under-the-radar additions. The organization has had plenty of success with that in recent years, including that trio of departed high-leverage relievers from this past season.

Whether it be a smaller free-agent contract (even on a minor league deal with a spring training invite), a trade or a waiver claim, expect that be the main course of action when it comes to adding relievers.

Figure Out the Position-Player Puzzle

One of the biggest objectives for the Cubs this winter is figuring out how to replace Kyle Tucker’s production. Yes, he had struggles in the second half that may have turned some fans off of him. Still, when he was right, he was a major catalyst for the offense, and Chicago has to somehow fill that role.

However, with the number of position players remaining from last season, that won’t necessarily be an easy task.

As the starting lineup stands, the Cubs will return both Carson Kelly and Miguel Amaya as the catching tandem. Michael Busch, Nico Hoerner, Dansby Swanson and Matt Shaw make up the infield, and Ian Happ and Pete Crow-Armstrong will reclaim their spots in left and center field, respectively.

How Chicago will fill the two remaining starting spots — designated hitter and right field — is currently a bit unclear.

Seiya Suzuki played 102 games at DH last season, but he’ll likely retake more of the load in right in 2026. It’s possible Owen Caissie and Kevin Alcántara get time in right field and give Suzuki more opportunities to just worry about hitting, though Moisés Ballesteros would also mix in at DH.

Rolling with the roster as is would require manager Craig Counsell to get creative with playing time. But that doesn’t necessarily mean the offense would be at the level it needs to be.

Could the Caissie/Ballesteros/Alcántara mix provide a similar level of production to what they’d be losing in Tucker? It’s possible, but far from guaranteed. To help, the Cubs could bring in an outside bat — one with more big-league experience than their young but promising hitters.

One obvious course of action would be just bringing Tucker back to Chicago. The potential length and cost of the contract he might receive make that seem very unlikely at this point, though.

Reuniting with an ex-Cub like Cody Bellinger or Kyle Schwarber would bring in a left-handed bat. Bellinger would also be able to take over in right field (and also spell Busch at first base when necessary), while Schwarber would give them a full-time DH with proven power numbers. But those reunions haven’t really had any steam in the rumor mill.

According to reports, including from The Athletic, Chicago has renewed interest in Alex Bregman, who they pursued but didn’t land last offseason. Matt Shaw developed into a Gold Glove finalist at third base in 2025, but his bat had its ups and down. Bringing in Bregman, then, would inject a more accomplished hitter into the lineup at third base.

That would also likely mean Shaw moves into a utility role. That may not be the best outcome for his long-term development, but mixed in with Caissie, Ballesteros and Alcántara, it would give the Cubs plenty of solid, young depth on the big league roster.

Chicago may not end up bringing in anything more than a bench bat or two to fill out the position-player side. It’s certainly possible the Cubs let the kids play, giving Shaw, Caissie, Ballesteros and Alcántara larger roles throughout the season.

Whichever route they do ultimately take, they have to figure out how to put together a playoff-caliber lineup for 162 games.