Friday, November 6, 2026 — the Cubs are in on the market’s biggest prize, but history says they rarely go this big.
The race for Tarik Skubal is taking shape, and the Cubs want in. Free agency opened to all 30 teams on Monday evening, and according to ESPN’s Jeff Passan, Chicago wants the two-time Cy Young winner “badly.”
The Case for Chicago
The fit is obvious. Jed Hoyer has said the Cubs’ offseason will focus mostly on pitching, and adding the best pitcher on the market would transform their rotation. Chicago’s projected 2027 luxury-tax payroll sits at about $168.9 million, leaving meaningful room under the threshold.
Skubal is also not attached to a qualifying offer, because he was traded midseason from Detroit to Los Angeles. That means signing him wouldn’t cost the Cubs a draft pick.
The Case Against
There is skepticism within the Cubs’ own organization about whether they can win a bidding war, Passan reported, and they could balk if the price climbs well above $300 million. That would be a massive break from their history: the largest contract the Cubs have ever given is Jason Heyward’s eight-year, $184 million deal.
The Competition
The Mets and Dodgers remain the two likeliest destinations. Los Angeles traded for Skubal at the deadline and has said it wants him back. New York has payroll flexibility and an owner, Steve Cohen, expected to push for a deal. The Yankees could consider him as well, possibly trading a starter to make room, and the Tigers may monitor the market in case his price drops — though that seems unlikely.
The Timeline
The expectation is that Skubal signs before the CBA expires on December 1, and some in the industry believe a deal could come as soon as next week’s GM Meetings. Skubal turns 30 on November 20. His 2026 line: a 2.72 ERA, 0.96 WHIP and 186 strikeouts in 158⅔ innings.
The Read
The Cubs’ interest is real, and their payroll gives them room. But wanting Skubal and paying for him are two different things. Unless Chicago is willing to obliterate its own spending record, it may end up as the team that drives up the price for someone else.
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