Chicago Cubs Risk Brutal 2027 Outlook if $22 Million Starter Walks

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SAN DIEGO, CALIFORNIA - SEPTEMBER 29: Manager Craig Counsell #11 of the Chicago Cubs looks on before game one of the National League Wild Card Series against the San Diego Padres at Petco Park on September 29, 2026 in San Diego, California. (Photo by Orlando Ramirez/Getty Images)

The Chicago Cubs were dropped from the Wild Card Series after the San Diego Padres won Games 1 and 2.

Trouble is now rounding the corner for the Cubs as they enter the offseason.

Free agency will drastically impact their 2027 campaign.


Chicago Cubs Must Retain $22 Million Starter

Shota Imanaga
GettyCHICAGO, ILLINOIS – AUGUST 05: Shota Imanaga #18 of the Chicago Cubs delivers a pitch against the Los Angeles Dodgers at Wrigley Field on August 05, 2026 in Chicago, Illinois. (Photo by Michael Reaves/Getty Images)

Early in 2024, Chicago finalized a deal with Japanese southpaw Shota Imanaga.

But now, he is set to become a free agent, which could leave the Cubs in a predicament.

As noted by Tim Kelly of Bleacher Report, the 33-year-old arm, “The Cubs may have hoped Imanaga would decline their QO last offseason, setting them up to receive draft-pick compensation if he signed elsewhere. This time around, Jed Hoyer and company will be left empty-handed if Imanaga walks.”

Last year, the two parties couldn’t agree to terms until a one-year, $22.025 million qualifying offer was issued.

During his 2026 campaign, he logged a 3.77 ERA and 174 strikeouts across 174.1 innings pitched through 32 starts. He walked 37 batters along the way.

This was a season filled with trouble in the pitching department, and Imanaga walking would undoubtedly add to this.

“The Cubs don’t seem to have the pitching system in place, organizationally, to be able to churn out many of their own wins, which means shopping for bargains each offseason,” Matt Snyder of CBS Sports noted.

Not only is Imanaga entering free agency, but so is valuable starter Kevin Gausman. The departure of these two alone will be enough to derail Chicago if something isn’t done in time.


Snapshot of the Chicago Cubs’ 2026 Campaign

Shota Imanaga
GettyCHICAGO, ILLINOIS – AUGUST 30: Shota Imanaga #18 of the Chicago Cubs reacts after giving up a three-run home run to Héctor Rodríguez #43 of the Cincinnati Reds (not pictured) during the fourth inning at Wrigley Field on August 30, 2026 in Chicago, Illinois. (Photo by Michael Reaves/Getty Images)

Chicago wrapped up its regular season riding an 89-73 overall record in the National League Central.

This placed them below the Milwaukee Brewers (103-59), but still a great distance away from edging them out.

The Cubs advanced to the Wild Card Series, but they dropped both games to the Padres, leaving loyal fans in dismay.

Game 1 resulted in an 8-0 loss on Tuesday, Sept. 29, and Game 2 finished 4-1.

Chicago is now eliminated from the postseason, and San Diego is entering the NLDS against the Brewers.

With such a frustrating ending to their 2026 season, something must change.

Imanaga and the pitching staff aside, Snyder wrote, “I’m not suggesting that Hoyer or general manager Carter Hawkins should definitely be fired, but I’m not sure either move should be off the table. I’m not necessarily saying the front office needs to spend more, either.”

As the Cubs enter the offseason, president of baseball operations Jed Hoyer has some difficult decisions to consider, and so do those around him.

Imanaga is a good starting point, but the work certainly won’t end there.

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Chicago Cubs Risk Brutal 2027 Outlook if $22 Million Starter Walks

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