Chicago's offseason is underway, and the Cubs' free agent pitchers could tell the story. Multiple key pitchers are set to enter free agency. Looking at the Cubs' players with options , the list gets longer. However, since that is hard to predict right now, we will focus strictly on the pitchers entering free agency. Minor League pitchers move teams frequently, but four key Major League pitchers could be on their way out.
One of the biggest Cubs free agent pitchers is Shota Imanaga . The lefty has been a key part of the rotation for the past three seasons. In that time, he is 35-21 with a 3.45 ERA. In 492.1 innings, he has 465 strikeouts. This past season, he was one of the Cubs' most durable pitchers, appearing in 174.1 innings. Imanaga went 11-10, with a 3.77 ERA and 174 strikeouts.
Quality left-handed pitchers can be expensive to get and even harder to keep. However, Imanaga is not an easy call to keep. He allowed 35 home runs. This was the second most in the league. It kept up the trend from the previous season; he just threw down the middle of the plate too much.
When in control, he can be dominant. The home run issue is just too much to overlook. I am a big Imanaga fan, but giving him over $2o million a year is just too difficult. Pitching is one of the Cubs' biggest needs , but they need to be smart with how they spend their money. There's a world where he returns to Chicago, but other teams will pay a lot of money for quality left-handed pitching. A bidding war would likely leave him as one of the Cubs' free-agent pitchers leaving Chicago.
Another key piece who could be out is Kevin Gausman . The veteran was acquired at the trade deadline, but didn't have a massive impact. After joining Chicago, he went 4-2 with a 4.83 ERA. This led to a postseason start, where he allowed three runs in 3.1 innings. At times he looked great; other times just solid.
Sep 30, 2026; San Diego, California, USA; Chicago Cubs pitcher Kevin Gausman (12) delivers a pitch in the first inning against the San Diego Padres during game two of the Wildcard round for the 2026 MLB Playoffs at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images
Of the four Cubs free agent pitchers, he is the one I have the hardest time seeing return. Even when he was moved at the deadline, it was clear he was a rental. Many thought he could return to Toronto after the season. I think Chicago would want to get younger, and Gausman has reached his ceiling. It wasn't a long time, or an elite time, but he gave Chicago solid play.
David Peterson saw a vastly improved season after joining the Cubs. The veteran lefty went 6-2 with a 3.70 ERA after being traded to Chicago . Chicago's elite defense helped take his reliance on ground balls to the next level. It felt like a match made in heaven, and the two sides benefited from the low-cost move.
Now, the issue is that it may not be low-cost to keep him. Peterson proved that he is a quality pitcher when backed by a strong defense. As I mentioned with Imanaga, lefties are expensive. That being said, I don't think Chicago will need to break the bank to keep him. Of the Cubs' free agent starters, Peterson coming back feels fairly realistic. They may want a higher-upside talent, but this could be a good re-signing to stabilize the rotation.
Aaron Civale may be the most under-the-radar player among the Cubs free agent pitchers. He isn't as flashy as the others but is a nice weapon. For two straight seasons, he has pitched better in Chicago than elsewhere. In 2025, he had a 2.08 ERA in 13 innings with the Cubs. He left for the Athletics and had a 5.42 ERA in the first half of 2026. When he came back to Chicago, he had a 1.72 ERA in 36.2 innings.
Every time he was called on, he stepped up. This was both for single innings and to fill the gap when starters got pulled early. Because of his inconsistent history, it is hard to see him getting a large deal. At the bare minimum, Chicago needs to look at what it would cost. He would be able to slot in as a solid arm to give the bullpen more consistency.
The Cubs free agent pitchers have the chance to heavily impact Chicago's offseason. The biggest focus needs to be on the pitching. Whether it is through the player with options, or free agents, they likely need to bring back a few familiar faces. Hard decisions will need to be made, and only time can tell which players get to run it back with the Cubs' elite defense.
Main Photo: Kamil Krzaczynski-Imagn Images
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