How ludicrous is the idea of the Cubs signing Tarik Skubal?
Very ludicrous. But it shouldn't be.

The Jed Hoyer Cubs have a lot of things to be embarrassed about. Scoring one run in two payoff games. Spending barely 26.5 hours in the playoffs. Blowing home field with a staggering finish to the season. Finishing second to the Brewers four years in a row. Being the only big market team in a division and not winning that division in a full season since 2017.
And worst of all, breaking their incredible streak of finishing with the fifth best record in the National League in the second half at four seasons.

The made a run at it, but their sad finish to the season this year opened the door for Arizona and they kicked it right down.

How sad.
Jed spent most of his end of the season press conference emphasizing that he knows they have to improve their pitching. He tried to dodge questions that laid the blame at the franchise's incredible decade and a half run of ineptness in drafting (or signing international prospects) and developing pitchers, but that root cause is so obvious that even Carter could probably figure it out.

OK, probably not Carter.
Despite just how bad their pitching was last year (and it was mostly very bad) there are a handful of guys the Cubs should try to bring back.
Jed kept repeating "we really feel like we blew a great opportunity" so often that he seemed like a lunatic. The 2026 Cubs were built (in his mind, at least) to win this year, and a big chunk of the team becomes free agents the day after the World Series ends. But the good news for Jed is that mostly the players who can leave aren't worth a shit. Seiya Suzuki will be a real loss. They might miss Carson Kelly. But it's long past time to be rid of Ian Happ and Caleb Thielbar.
With their trade deadline acquisitions the Cubs' payroll for the season was $269.2 million. They went over luxury tax threshold one, but with the CBA expiring on December 1, who knows if that means anything?
Their committed payroll for next season at one point was going to be very, very low. At one point in the offseason the only veteran signed to a real contract for next season was Dansby Swanson. Then they signed Alex Bregman and Phil Maton (woof) and extended Nico Hoerner and Petecrow Armstrong.
But how flexible is their payroll next year?
Very.