The Chicago Cubs have some decisions to make regarding their roster this offseason. 

The Cubs will need to decide which free-agent pitchers they want to bring back for the 2027 season. Players like Kevin Gausman, Shota Imanaga, Clay Holmes, Matthew Boyd, and David Peterson could all depart in free agency.

What is the likelihood each of those Cubs free-agent starters returns? Let’s dive in and find out.  

The Cubs made a big move at the trade deadline to acquire Gausman. His numbers with the North Siders, though, were mediocre. The veteran right-hander had a 4.83 ERA and 57 strikeouts over 50 ⅓ innings pitched. 

Although the Cubs would likely welcome back Gausman, there’s a strong chance that he returns to the team that traded him at the deadline. Mitch Bannon of The Athletic recently reported that the 35-year-old wants to return to Toronto.  

Likelihood: 20%

Imanaga put together another solid campaign in 2026. He had a 3.77 ERA, 1.096 WHIP, and 174 strikeouts over 174 ⅓ innings pitched. The southpaw was also the Cubs’ best pitcher down the stretch, with a 2.25 ERA in the final month. 

However, Imanaga might not return to the team. Patrick Mooney of The Athletic recently reported that the writing may be on the wall for the left-hander's return to Chicago. That puts his likelihood of returning low. 

Likelihood: 15%

The Cubs and Holmes are really a match made in heaven. Holmes is an extreme groundball pitcher, while Chicago has an elite defense. For a pitcher who ranked in the 99th percentile in groundball rate this past season, there’s appeal for the right-hander to return in 2027. 

Now it’ll all depend on what Holmes actually commands in free agency. The 33-year-old is not technically a free agent yet, but the expectation is that he will decline his $12 million player option. That will give him the freedom to sign with any team. 

Likelihood: 50%

Boyd regressed a bit from his All-Star campaign in 2025. He posted a 3.91 ERA, 1.208 WHIP, and 96 strikeouts over 126 ⅔ innings pitched. The southpaw also gave up four runs across four innings in Game 1 of the National League Wild Card Round. 

There hasn’t been much talk about whether the Cubs want to bring Boyd back. But he is 35 years old and could get a nice payday after back-to-back solid pitching seasons. 

Likelihood: 35%

Peterson will command the least amount of money in free agency from this list, which is why there’s a strong possibility that he does return to the team. He’s definitely a pitcher the Cubs should be looking to bring back on a cheap deal.  

The former All-Star pitcher had a 3.70 ERA and a 1.369 WHIP across 80 ⅓ innings pitched with the Cubs in the back half of the season. Those numbers should play well in that No. 4 rotation spot next year. 

Likelihood: 50%