The Chicago Cubs find themselves at a pivotal offseason in terms of building a rotation capable of sustaining a deep postseason run. Injuries and limited depth exposed vulnerabilities in the starting pitching corps during the postseason, and the front office is now faced with several pressing decisions.
When the Cubs advanced to the National League Division Series, their rotation was already hobbled. Rookie prospect Cade Horton was sidelined by injury, Shota Imanaga failed to find consistent form, and veterans Matthew Boyd and Jameson Taillon were asked to carry heavier workloads than ideal. President Jed Hoyer openly acknowledged the need for greater depth on the mound.
The first major decision involves Imanaga, who could have remained in Chicago under a three‑year option worth $57.75 million, but the team declined that, and Imanaga opted against a one‑year $15.25 million player option, choosing instead to explore free agency. The Cubs now must decide whether to extend a qualifying offer (about $22 million) to retain compensation rights if he signs elsewhere, or to attempt a re‑signing with a new deal.
With Imanaga potentially gone, the rotation’s foundation currently rests on Boyd and Taillon, both under contract for 2026, and on the veteran Rea (if the Cubs pick up his $6 million option). The left‑handed Steele, once an All‑Star and Cy Young contender, is returning from left elbow surgery and remains an important part of the plan, though his availability early in the season is still uncertain. Behind that core, rising arms including Horton, Assad, Brown and Wicks will be counted upon. Also in the wings is top prospect Jaxon Wiggins, ranked No. 67 on MLB Pipeline’s Top 100 list and likely to break into the majors in 2026.
The third piece of the puzzle is how aggressively Chicago will pursue outside help. Their front office previously explored pitching trades at the deadline but balked at the asking prices. Sophisticated names ouf there include Sandy Alcántara, Joe Ryan and MacKenzie Gore. On the free‑agent front, high‑end options for the Cubs include Dylan Cease, Framber Valdez, Michael King, Ranger Suárez, Zac Gallen and Merrill Kelly. Whether the Cubs shop aggressively or opt for internal growth will shape their trajectory.
Looking ahead to 2026, the Cubs are looking to turn their good position into something more sustainable. Depth, consistency and a clear rotation plan will be critical if they are to convert their regular‐season momentum into a lasting postseason push. With the rotation in transition, the coming months may be as defining as any in the organization’s recent history.
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