Cubs Urged to Pursue Blockbuster $149.5 Million Offseason Move

The Chicago Cubs must prioritize starting pitching this offseason after their rotation is projected to lose four key pieces to free agency, according to an analysis published by Cubs Roundtable.

Shota Imanaga and Kevin Gausman are set to become unrestricted free agents, while Matthew Boyd’s mutual option and Clay Holmes’ player option are expected to go unexercised, leaving both likely headed to the open market as well.

The Cubs could attempt to re-sign one or more of those pitchers, given their familiarity with the organization and some solid contributions during the 2026 campaign, the report noted.

However, reports suggest Imanaga’s return is in doubt and that Gausman could return to Toronto to finish his career, leaving the status of Boyd and Holmes uncertain at best.

Regardless of retention efforts, Chicago needs to add multiple starters this winter, including a true No. 1 who can deliver in high-leverage situations, the analysis argued.

The Cubs lacked such an ace in the postseason, as Boyd allowed four runs in four innings in Game 1 of the National League Wild Card Series and Gausman surrendered three runs in 3 1/3 innings in Game 2.

Tarik Skubal, the two-time American League Cy Young Award winner, represents the ideal solution as one of baseball’s premier pitchers, according to the Roundtable piece. Acquiring Skubal would require a commitment exceeding $300 million, a figure the analysis suggested ownership under Tom Ricketts is unlikely to approve.

Instead, the Cubs should turn to San Diego Padres right-hander Michael King, who holds a player option for the 2027 season that he could decline, positioning him as a free agent.

King finished the 2026 regular season with a 12-10 record, 3.21 ERA, 1.18 WHIP and 159 strikeouts across 185 innings in 32 starts.

The 31-year-old also dominated the Cubs in Game 1 of the NL Wild Card Series, tossing seven shutout innings with eight strikeouts.

King’s contract includes a $28 million player option for 2027 (or a $5 million buyout) and another option for 2028, giving him leverage to test the market after a healthy, productive year.

Spotrac projects King to be worth around $149.5 million over five years, a valuation that would place him among the more attainable high-end options in a free agent class dominated by longer and costlier commitments.

Signing King would upgrade the Cubs’ rotation and provide the front-line starter the team missed during the 2026 playoffs, the analysis concluded.

The Cubs face a broad free agent class headlined by Skubal, but King offers a more attainable path to addressing their most pressing roster need while remaining within a more realistic spending range.