The Chicago Cubs and Shota Imanaga can take the rest of October to reflect on a largely successful season that ultimately ended in disappointment.
In assessing Imanaga’s intricate contract situation, a conservative front office guided by data-driven models, and a Japanese pitcher once nicknamed “The Throwing Philosopher,” will not want to make any reactionary decisions.
Cubs president of baseball operations Jed Hoyer is scheduled to hold his end-of-season briefing with the Chicago media on Wednesday at Wrigley Field. Knowing Hoyer’s deliberate style, it’s unlikely that he will use that forum to make any definitive statements about Imanaga’s future.
To recap, Cubs officials and Imanaga’s representatives finalized a four-year, $53 million contract in January 2024. The creative agreement included a series of club/player options, to maintain some flexibility as the left-handed pitcher assimilated into American culture and experienced Major League Baseball’s steep learning curve.
This explainer, based on information from league sources, maps out where the two sides could be heading.
• By exercising their option, the Cubs can lock in Imanaga for the 2026, 2027 and 2028 seasons at a total cost of $57.75 million.
With a fifth-place finish in last year’s National League Cy Young Award voting, Imanaga triggered salary escalators over the duration of the deal. A dazzling rookie performance (15-3, 2.91 ERA) initially made the idea of that three-year commitment seem like a no-brainer.
Those terms are in the organization’s comfort zone, part of a collaborative process that has consistently identified solid starters such as Jameson Taillon and Matthew Boyd. For reference, the Cubs have not signed a free agent at the top of the pitching market since 2018 – and Yu Darvish ended up getting traded midway through a six-year, $126 million contract in a pandemic-driven, salary-dump deal with the San Diego Padres.
For most of this year, Imanaga (9-8, 3.73 ERA) performed quite capably for a team built on pitching and defense. He pitches with some charisma and a certain kind of flair, enlivening the atmosphere for his starts at Wrigley Field. His success also gives the Cubs more credibility as they try to recruit the next waves of Japanese talent.
But this is also an analytical group that will try to project a pitcher who turned 32 last month. Imanaga missed most of May and June with a strained left hamstring and then allowed 15 home runs in August and September.
In October, Imanaga pitched relatively well in a loss to the Padres in the Wild Card Series. He then got knocked out in the third inning of a Division Series loss to the Milwaukee Brewers. Rather than start him in the decisive Game 5 at American Family Field, the Cubs unsuccessfully went with an opener and a bullpen plan, which seemingly added to this uncertainty.
• If the Cubs decline their option, Imanaga would gain a $15.25 million player option for 2026. He would also have another player option for 2027, meaning he would be guaranteed at least $30.5 million over the next two seasons.
In that scenario, Imanaga would very likely decline his player option for next season. He’s a proud, competitive individual who pitched in the All-Star Game last year. Good pitching is hard to find, and is a fragile thing to maintain.
The Cubs, however, could then make Imanaga a one-year qualifying offer worth slightly more than $22 million, a move that would tie his free agency to draft-pick compensation and potentially limit his options.
In that case, Imanaga’s return would depend on what the market will bear. He could take the higher salary in the hopes of approximating another Cy Young Award-caliber season, or attempt to top the two-year, $30.5 million structure and seek more long-term security.
• This final scenario appears to be so remote that it’s almost not worth mentioning. But if Imanaga exercises his first player option, the Cubs would hold a two-year option for 2027 ($24.25 million) and 2028 ($18.25 million).
The Cubs have almost exclusively avoided financial commitments beyond the 2026 season, the current expiration date for the baseball industry’s collective bargaining agreement.
Despite the late-season slump, this has still been a very good partnership among Imanaga, his teammates, manager Craig Counsell and pitching coach Tommy Hottovy. Over Imanaga’s 54 starts in a Cubs uniform, the club has posted a .667 winning percentage.
The Cubs had only one pitcher, Boyd, make 30-plus starts this year. Their farm system features just one pitching prospect who has generated much buzz recently – and Jaxon Wiggins threw only 78 innings during the 2025 minor-league season.
Perhaps this October would have played out differently if Justin Steele and Cade Horton were healthy, but the reality is the Cubs did not have the pitching depth to survive and advance through multiple postseason rounds.
Even assuming that Steele and Horton should be ready around Opening Day 2026 – with no setbacks – the nature of the game is that more pitchers will continue to get injured.
Given Chicago’s large, stable group of position players returning next season, and how thin its pitching staff looked by the start of the NLDS, the top priority will be to add established pitching talent, not subtract.