REPORT: Cubs Expected to Pursue Free Agent Starter Dylan Cease This Winter ...Middle East

“According to MLB insiders I know, people in the know in other organizations, they feel the Cubs will be there among the top suitors (Dylan Cease) … I would say it’s highly likely – like for sure – that he’s going to be looked at by the Cubs and be continued to be pursued.”

Boom. There’s that first big Cubs offseason rumor we’ve been looking for (and discussed the absence of yesterday). Let’s get into it.

Cubs To Pursue Dylan Cease

According to Bruce Levine on Inside the Clubhouse (9:30 am segment), the Chicago Cubs are expected to pursue free agent right-hander (and their former draft pick) Dylan Cease this offseason.

Our @MLBBruceLevine says MLB sources have confirmed the #Cubs will have interest in SP Dylan Cease this offseason.Bruce and @DavidHaugh are talking about Cease and a possible return to Chicago now on Inside the Clubhouse! Hang here: t.co/6pC174BHJJ pic.twitter.com/CQx5mLjNgG

For those following along closely, this shouldn’t come as too much of a surprise. The Cubs have long been seeking a hard-throwing, right-handed pitcher to mix into their largely left-handed and/or softer-tossing rotation for a contrasting look. Indeed, that’s why they targeted guys like Edward Cabrera and Sandy Alcantara at the deadline (Joe Ryan, too, though he doesn’t throw quite as hard), and why I wrote yesterday that you should expect those names to pop back up in Cubs trade rumors again this offseason. But free agency is another way to go, and that path costs only money.

The issue, of course, is that Dylan Cease is represented by Scott Boras, who is not going to let a bad results season for Dylan Cease (4.55 ERA) ruin his narrative. Instead, Boras will likely point to the five straight seasons of 32+ starts, the near-career-best 97.1 MPH fastball velocity, his name recognition, the strikeouts, and the still very significant upside. At the end of the day, this is a durable, flame-throwing righty on the right side of 30, who has twice finished inside the top-4 of Cy Young voting.

There are some hurdles here, though, even beyond the big one (Boras, the cost, the Cubs’ general reluctance to spend big on long-term deals for free agent pitchers).

For one, Cease did have some issues this season. He failed to complete 5.0 innings in 10 of his 32 starts. And of the 22 other outings, he allowed 4+ earned runs five times. To think of that another way, 15 of his 32 starts can be best classified as “bad.” Not a great ratio.

For another, Dylan Cease is eligible for (and will rightly reject) the qualifying offer. And that will attach him to draft pick compensation — obviously, that will impact any team that attempts to sign him, but the Cubs tend to value that pick very highly, and they bake that value into any offer they’re willing to extend. The silver lining there is that if and when Kyle Tucker signs with another team, the Cubs will gain a compensation pick, themselves, neutralizing the potential loss of signing a qualified free agent like Cease, but still. It makes a deal with the Cubs a little harder to imagine.

And lastly, while Dylan Cease does offer the right combination of youth, upside, velocity, and handedness, there are other interesting free agent pitchers out there in free agency. Some will be pricey (Framber Valdez, Ranger Suarez, etc.). But plenty of others (Jack Flaherty, Zac Gallen, Merrill Kelly, Shane Bieber, etc.) should be more reasonably available. And seeing how well the Matthew Boyd model worked out for the Cubs last season, you could imagine them trying to follow a similar path in 2026.

Until we know what sort of deal Dylan Cease is actually looking for, it’s difficult to judge whether this rumored interest is legitimate … or just some very useful leverage the Cubs can use when negotiating with those players’ agents (or other trade partners).

Ultimately, I don’t think the Cubs are going to set the market for a qualifying offer guy like Dylan Cease, but perhaps there is an opt-out route that could make some sense. In other words, maybe Dylan Cease will want to come back to Chicago, where he spent five years with the White Sox, to reestablish his value as a top-of-the-rotation type of pitcher in a high-profile market (on a team that should probably be back in the playoffs again next Fall).

And personally, that does excite me. I’m aware of the flaws, but if the Cubs coaching staff and front office believe they have a good understanding of the pitcher (and, hey, Jed Hoyer was here when they drafted him), then I can definitely get on board with Cease being the target this offseason. I love guys who’ve flashed that sort of upside.

So is Dylan Cease my No. 1 Cubs free agent pitching target this winter? No. But I am happy to learn of this rumored interest, and I hope it at least signifies the type (and tier) of pitcher the Cubs will target this offseason.

Related reading:

What Are the Cubs Going to Do this Winter? Who’s Available in Free Agency?Here's a quick look at the players who might catch their eye. Position by position. t.co/gx8aJ64vvi

Four Cubs Trade Targets We’ll Probably Hear About This Winter t.co/TeNpRbTETC pic.twitter.com/qRthTIzUoy

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