What Does a Successful Cubs Offseason Actually Look Like?

Speculation is already surrounding the Chicago Cubs' offseason. With plenty of roster holes to fill, the team needs to find ways to improve and contend for a World Series title. It’s never that simple, but the opportunity is there, and it's very easy to get excited about the endless possibilities. At the same time, the Cubs fans need to set realistic expectations.

Would bringing in a player of Tarik Skubal’s caliber solve a big problem for the Cubs? Absolutely. He would give the Cubs a true ace on the staff. However, one player doesn’t solve all the problems this team faces.

Skubal may add an elite arm to the rotation, but the Cubs can't forget about the bullpen. And what about the position players? You have to decide whether to bring back Ian Happ and Seiya Suzuki. Signing someone like Skubal does make this team better, but not deep enough for a long playoff run. 

Indeed, the Cubs have to think hard about improving their all-around depth. Players like Skubal will demand a lot of money. He will reset the pitcher market. It doesn’t make much sense to put all your eggs in one basket when the basket has numerous holes.

With that in mind, let's talk about the steps the Cubs can take to truly turn this 2027 offseason into a success.

The Starting Rotation Needs Work

Focusing on the starting rotation, the Cubs need to build a combination of velocity and control. They need to add two solid starters. A player such as Michael King of the San Diego Padres makes a lot of sense. If he declines his player option, he becomes a free agent the Cubs must pursue. Like Skubal, King would also be the ace of the Cubs’ staff. 

Coming off a stellar playoff performance, including two deep no-hit bids, the Cubs would get the veteran leader they need with dominant playoff experience. In the 2026 postseason, King only gave up 5 hits, had a 0.64 ERA, and recorded 15 strikeouts. It was pure dominance when it mattered most.

Adding King would be a phenomenal addition, but the Cubs need more. Let’s revisit the 2026 trade deadline. Rumors had the Cubs trading for Reid Detmers from the Los Angeles Angels. Although it didn’t happen, the Cubs can pursue that option again. Detmers gives the Cubs a top-tier left-handed pitcher. It would cost the Cubs, but adding him to the rotation would be a huge win. 

Think about it: Adding both Michael King and Reid Detmers to the rotation would get the Cubs back into contention. They would headline the rotation, followed by Cade Horton. If healthy, Horton provides a solid third option, allowing for a slower recovery. It would let him ease back into the rotation without too much pressure to be the staff ace after a tough injury that cost him the entire 2026 season. 

The final two spots would be up for grabs. If healthy, Justin Steele is the clear option. The final spot depends on the cost and what the Cubs want to do. Do you give it to Ben Brown? Does Edward Cabrera suddenly turn around and earn that spot? Unlikely, but possible. Do the Cubs re-sign Matthew Boyd? Do they call up Jaxon Wiggins? They will have plenty of options.

The Bullpen Needs Reinforcements

The bullpen is President Jed Hoyer’s Achilles heel. It’s harsh but fair criticism. The bullpen cost the Cubs numerous close games they could have won and thus played a major part in erasing their home-field advantage. Now, Hoyer is looking to make some necessary adjustments to improve the bullpen.

Edward Cabrera will headline the bullpen whether Cubs fans like it or not. What will his role be? Manager Craig Counsell lost faith in him last year, but the Cubs have to see if there is anything they can get out of him. It would be a huge win and increase the depth they so desperately need. 

Ryan Zeferjahn will also play a major role moving forward. Like Cabrera, Zeferjahn struggled often, but he was a reliable pitcher when the Cubs needed him in the postseason. He provides the bullpen with stability and has elite stuff, including a hard fastball and a nasty curveball. The mix of pitches makes him a strong setup man for the Cubs. 

When healthy, you also can't look past Daniel Palenica. Just don't throw him in against left-handed hitters! The Cubs may want to be careful about the role they use him in, however. Pursuing a more dependable closer may be in their best interest.

Andrés Muñoz of the Seattle Mariners is the ideal target, but don’t expect him to reach the open market because he has a team option. Can the Cubs figure out a trade for him? Anything is possible. Realistically, Raisel Iglesias of the Atlanta Braves may be a better target for the Cubs. He earned 34 saves last year with 64 strikeouts and a 2.55 ERA. 

Cabrera, Palencia, Zeferjahn, and Iglesias, plus Colin Rea and the return of Phil Maton, could put the Cubs on the verge of building a reliable, deep bullpen. The team would need to add a left-handed reliever. A.J. Minter of the Minnesota Twins is an option to consider. That would be a major improvement, even if the Cubs don't sign that many free-agent bullpen arms.

Two Tough Decisions Must Be Made Regarding the Positon Players

The position players are essentially set. Not much change is expected, but the Cubs do have decisions to make on both Ian Happ and Seyia Suzuki. Although Ian Happ has struggled at times, it would probably be best for the Cubs to re-sign him, especially with rumors that he is considering taking a hometown discount.

If the Cubs re-sign Happ, don't expect them to re-sign Seiya Suzuki. The holes on the team would be right field and the catcher position. However, if the Cubs focus on pitching in the offseason, then the Cubs would be better off bringing back Carson Kelly and Miguel Amaya. It has worked for the Cubs, so why fix something that isn't broken?

With Suzuki leaving, can top prospect Ethan Conrad win a roster spot after the dominant performances he’s had in the minors? Expect him or Josiah Hartshorn to eventually win the other corner outfield spot opposite Happ. The Cubs are in a position to make some moves this offseason.

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