It’s that time of year again, with the 2026 season in the books. Free agent season!
Only this year, it’s different, because only a few weeks from now, MLB owners are likely going to lock out MLB players and all transactions, along with everything else in MLB, will stop. This could lead to a lot of signings over the next few weeks, as I noted in this article last month.
In this series I’m going to look at some players who the Cubs could target in free agency, guys who could be useful to the team in different
areas. I’ve already done that for the Cubs’ own free agents in this series from last month. For this series I’m going to be working off of MLB Trade Rumors’ Top 50 free agent list, though I won’t write about absolutely everyone on the list.
So, Tarik Skubal. Clearly the top free-agent pitcher, clearly one of the best pitchers in baseball. He turns 30 in a couple of weeks and has had three outstanding seasons in a row, after missing some of the 2023 season with elbow issues. (He also had some of those this year, but came back from a “loose bodies” elbow procedure with no apparent ill effects.)
Various sources have projected him to get a contract between eight and 10 years with a total value of $350 million to $500 million. MLBTR says nine years, $425 million, or an AAV of $47.2 million.
Let’s stop right here. You know the Cubs aren’t going to do that. I know the Cubs aren’t going to do that.
I’m here to argue that the Cubs shouldn’t do that, even if they could.
Well, that’s provocative. Let me explain.
All five of the pitchers in the Cubs’ rotation at the end of the 2026 season — Shōta Imanaga, Kevin Gausman, David Peterson, Clay Holmes and Matthew Boyd — are free agents. Beyond that, the next-up group, Ben Brown, Cade Horton and Justin Steele, all had various forms of injuries in 2026 and what they can contribute in 2027 is uncertain.
So that leaves… Javier Assad and what army?
With Skubal expected to get an AAV of at least $40 million and perhaps $50 million, what would that leave for the Cubs to sign other pitchers? Skubal can’t pitch every game.
Should the Cubs spend that much on free-agent pitchers (or on those they acquire by trade)? Absolutely, positively yes. They need to invest in pitching infrastructure and stop trying to patch the sinking ship, as they did this year. And in my view, the best way to do that — if they’re going to invest $50 million in that infrastructure this winter — would be to use it on multiple pitchers. Guys who might not be Cy Young candidates, but maybe No. 2 guys. I’ll talk about some of those guys in upcoming installments in this series.
Maybe you don’t agree with me or believe me. Maybe you’ll believe ESPN’s Jeff Passan:
The Chicago Cubs badly want Skubal. They also are skeptical that they will be willing to compete at the sort of dollars Skubal is expected to get — well in excess of $300 million, potentially in the $400 million-plus range.
And that’s exactly my point. The Cubs don’t have to sign the guy who makes the most money to succeed. In fact, they did spend quite a bit of money last offseason on Alex Bregman, and after a slow start for the third baseman, that worked out just fine.
If the Cubs do want to compete, spread out that money over multiple pitchers. Don’t put it all on one guy.
I’m sure you’ll tell me why I’m wrong, so have at it. But my stance is: Pass on Skubal. Spend the money? Absolutely. Just do it elsewhere.
