When Shota Imanaga opted out of free agency, questions emerged around the Chicago Cubs: would the left-hander return to the North Side, or had his time with the organization reached its end? The front office extended a $22.025M qualifying offer after Imanaga declined his $15.25M player option. So is he staying? Well, it’s still uncertain. And the front office isn’t sitting idle; they have expanded their search beyond the Japanese left arm.

The Cubs have identified two free agent pitchers who could reshape their 2026 rotation. It’s the Padres duo: Michael King and Dylan Cease. According to Spotrac, King carries a market value of $92 million, while Cease is valued at $185 million, totaling $277 million.

Both pitchers declined their options to enter free agency. In the injury-plagued 2025 season, King made 15 starts with a 3.44 ERA and 76 strikeouts in 73.1 innings. However, shoulder and knee issues led to a 6.11 ERA in his final five starts.

Cease completed 32 starts and threw 168 innings, finishing with a 4.55 ERA and an 8-12 record, while achieving 215 strikeouts for his fifth consecutive season over 200 strikeouts.

MLB Network’s Jon Morosi provided insight into the Cubs’ strategic approach during a recent broadcast, confirming the team’s interest spans multiple starting pitchers. “Focus on the pitching now for the Chicago Cubs because you’re right. They are interested in multiple starting pitchers. The Athletic had this report. Dylan Cease is on their list. Michael King is on their list.”

Morosi emphasized the historical connection with Cease and King’s upside despite injury concerns. “But Dylan Cease, I would love this fit with the Cubs. They’ve tried to bring him back on several occasions. Remember, he was originally a Cub before he was traded to the White Sox in the Jose Quintana deal. Michael King, elite stuff. He misses bats with the best of him. Now, he did have some injuries with the Padres this past year, but it seems that, right now, the indications are that he is healthy and ready to go. I think Michael King is a name to watch there as a potential fit for the Chicago Cubs.”

So, is this a done deal? Well, as per the insider, “the Cubs make any decisions quite yet until Imanaga makes his choice. 4 p.m. Eastern Time Tuesday.” Imanaga had a 3.73 ERA in 25 starts in 2025 with 117 strikeouts, but faced challenges, including 31 home runs allowed—20 in his last 12 starts—and a hamstring injury.

His postseason was tough as well, posting an 8.10 ERA in two starts with three homers allowed in 6.2 innings. Despite this, the team is awaiting his decision before making further moves.

As per reports, Michael King could be a budget-friendly addition to the rotation, showcasing elite strikeout ability when healthy with his effective sweeper.

Cease, meanwhile, brings his own compelling narrative. The 29-year-old was initially drafted by the Cubs before the 2017 trade to the White Sox, making a potential return full circle for the right-hander.

Brett Taylor of the BN Cubs Podcast recently discussed concerns regarding Cease and the aging curve for starting pitchers. “When it comes to starting pitchers and the aging curve, what you see is 90% of pitchers have a moment—29, 30, 31, 32, or so—where they will lose a couple clicks on their fastball and some of the sharpness on their breaking pitches.”

Cubs president of baseball operations Jed Hoyer addressed the team’s offseason approach at the GM meetings. “We’re going to have an active offseason,” Hoyer said. “Take that for what it’s worth.” The Cubs’ rotation beyond Justin Steele currently includes Matthew Boyd and Jameson Taillon under contract for 2026.

Imanaga’s qualifying offer decision deadline is November 19th at 4 p.m. Eastern.

If he accepts, he returns. If he declines and signs elsewhere, the Cubs receive draft pick compensation and can redirect resources toward other pitching targets like King or Cease. And if any of them do not fit the plan, they might circle pitcher from the Houston.

Left-Handed continuity as the Cubs look towards the Astros pitcher

As per reports, the Cubs might go for Framber Valdez, who will soon be a free agent after playing for the Houston Astros. They could use him to fill the vacuum left by Shota Imanaga. Valdez is widely seen as the best starting pitcher on the market this winter. Chicago is expected to offer him a four-year, $114 million deal.

It makes sense because Valdez throws from the left side as well. This means that Valdez could easily step into the role that Chicago had in mind for Imanaga. That kind of continuity could make the rotation change easier, without a significant shift in the club’s mindset.

Valdez has played in the playoffs before and has a history of durability and of pitching ground balls, which are important to the Cubs as they try to be more consistent.

The Chicago executive management has made it clear to the public that their #1 focus this offseason is beginning pitching. Olivier speculates that Valdez could be their top target rather than a backup.

For now, nothing is specific. A transaction of this size would require significant payroll room and carry long-term risk.

If the Chicago Cubs sign Framber Valdez to the rumored four-year, $114 million deal, their investment in the rotation would immediately go well above the $277 million they spent on Dylan Cease and Michael King.

The decision timeline hinges on Imanaga’s response to the qualifying offer.