Chicago Cubs pitcher Shota Imanaga warms up before a baseball game against the Colorado Rockies, Saturday, Aug. 30, 2025, in Denver. (AP Photo/David Zalubowski)

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As the baseball offseason approaches, the Cubs have a number of questions to answer about what their 2026 roster will look like. Things like whether to extend a long-term contract offer to Kyle Tucker and whether to pursue starting pitcher Dylan Cease in free agency. The latter might come down to another decision the Cubs front office has to make this winter: Whether to pick up Shota Imanaga’s contract option that would keep him in Chicago for three more years or let him walk after just two seasons in a Cubs uniform.

The first option would mean paying Imanaga another $57 million and keeping him in the rotation through the 2028 season on a contract with a no-trade clause. If they don’t choose that route, then things get a little more complicated. There’s a scenario where Imanaga gets a one-year option for 2026, but it’s a risky one for him considering his age, so he is not likely to take that option. There’s also a scenario where the Cubs decline the aforementioned three-year option and offer him a qualifying offer of probably one year and about $22 million, also probably not something Imanaga would be inclined to accept.

Not that long ago, it might have looked like an easy choice to keep Imanaga in Chicago for three more seasons. But his struggles down the stretch of the 2025 regular season and in the playoffs may have muddied those waters a bit.

“When we signed Shota, if you would have sort of shown us his production over the last two years, you would have taken that in a heartbeat,” Cubs president of baseball operations Jed Hoyer told reporters at the end-of-season press conference. “So not only has he produced for us, but he’s just a great teammate, a terrific asset to the organization.”

Again, while Imanaga’s overall numbers look good, a troubling tendency to give up home runs emerged for him late in the season, particularly in September. Imanaga allowed 20 home runs and posted a 5.17 ERA over his final 12 games. That tendency made Imanaga hard for Cubs manager Craig Counsell to rely on during the playoffs and contributed to their failure to advance past the Brewers in the NLDS. He gave up two home runs in his Game Two start of the division series, one that proved to be a crucial loss for the Cubs.

But it’s possible that this small sample of starts won’t sway Hoyer’s decision. Under different circumstances, it’s just a pitcher having a rough stretch over the course of four weeks or so, and an experienced pitcher like Imanaga can usually be trusted to make adjustments and bounce back. Perhaps it’s just the timing of this bad patch of starts that has made it seem like picking up Imanaga’s three-year option isn’t so obvious a decision.

Doing so would add significantly to the Cubs’ payroll for next year, and that could impact their approach to players like Tucker and Cease, along with any other free agents they are hoping to lure. Spotrac’s payroll projections for 2026 have the Cubs sitting well below the $244 million first tier of the luxury tax threshold, so there is room to spend, but keeping Imanaga and Tucker would chance their payroll status notably.

“Obviously, we have decisions to make, and we have discussions to make, and over the next two or three weeks, we’ll do that,” Hoyer told reporters. “But I’ve got nothing but positive things to say about Shota.”

Hoyer has many decisions to make this offseason, Imanaga being just one of them. In many respects, 2025 was a very successful season for the Cubs. They improved by nine wins over their 2023 and 2024 seasons and reached the playoffs for the first time since 2020. They won a playoff game and a playoff series for the first time since 2017. Their victory in the wild card round over the Padres this year was the first time the Cubs had won either a postseason game or a postseason series since they beat the Nationals in the division series and then won one game in the championship series against the Dodgers eight years ago.

That gap in time represents the falling off from the expected competitive window the Cubs thought they had opened when they reached the NLCS in 2015 and then won the World Series the following year. Though the Cubs went back to the NLCS in 2017, the won just one of the games in that series and had not had any postseason success since then. By 2021, they were trading away nearly every member of that championship core and moving on from the hopes brought by the 2016 team.

To Hoyer’s credit, since taking over for Theo Epstein as the president of the organization, he has rather quickly rebuilt the ballclub into one that could get back to the playoffs and have some amount of success. But the paradigm in Chicago and among the Cubs fanbase has shifted in the last ten years, and more than just getting there is expected. This winter, Hoyer has a chance to keep moving forward from the success of the past season, and deciding what to do with Imanaga will be a big part of that process.