The Chicago Cubs are coming off a season that saw them take a meaningful step forward — but not quite enough of one. A postseason berth and near–NLCS run marked real progress, yet it also exposed the gap between Chicago and the true heavyweights of the National League.

The Dodgers just won back-to-back World Series titles and are already rumored favorites to sign Kyle Tucker — maybe the Cubs’ best player in 2025 — in free agency. Los Angeles isn’t slowing down. That’s the standard. That’s the gap Jed Hoyer and company need to close this winter.

The offense remains a priority, but Chicago’s best path to contention might start on the mound. Their rotation was good enough to get them to October — just not deep enough to win there. That’s why heads turned when reports surfaced of a possible reunion with former top prospect and ex–White Sox ace Dylan Cease.

Jim Bowden tabbed the Cubs as a potential fit for cease in his Top 50 free agents column. And according to Bruce Levine, the Cubs are expected to pursue Cease in free agency. But what kind of fit would this actually be?

The Player

Dylan Cease has been everything from a Cy Young contender to a struggling mid-rotation arm over the course of his big-league career.

After being traded by the Cubs to the White Sox in the 2017 José Quintana deal, Cease debuted in 2019 and gradually developed into one of the American League’s most electric arms. His 2022 season remains the high point — a 14–8 record, 2.20 ERA, and 6.4 WAR that led the league, culminating in a second-place finish for the AL Cy Young Award.

He took a step back in 2023 with the White Sox but rebounded nicely after being dealt to San Diego. With the Padres, Cease went 14–11 with a 3.47 ERA and 224 strikeouts across an MLB-leading 33 starts. He’s the only pitcher in baseball to make 32 or more starts in each of the last five seasons — a rare mark of durability.

2025 wasn’t his best year statistically. His control wavered again, leading to a 1.32 WHIP and 4.55 ERA. Still, he punched out 215 batters — and dominated the Cubs when it mattered most, throwing 3.2 shutout innings with five strikeouts against them in Game 2 of the NL Wild Card Series.

Even when Cease isn’t at his peak, his stuff is overpowering enough to change a game — the kind of arsenal built for October. That’s something the Cubs’ current rotation, talented as it is, doesn’t quite have.

The Contract

Even coming off a down season, Cease’s representation — led by Scott Boras — guarantees he won’t come cheap.

Over the last five years, Cease has averaged more than 220 strikeouts per season with a 3.72 ERA. Those are the numbers his market will reflect, not one inflated season ERA.

Spotrac projects his market value at seven years, $185 million — roughly $26 million per year. Bowden’s projection was even steeper: six years, $187 million, or over $31 million annually.

That’s a hefty price, but it’s the going rate for a durable, high-strikeout starter who can post a sub-4.00 ERA and take the ball 32 times a year. The Cubs have the money to spend — and a rotation that might be one ace short of being truly elite.

With Justin Steele, Cade Horton, Shota Imanaga, Matthew Boyd, and Jameson Taillon already in the mix, Chicago doesn’t need to overhaul the staff. They just need one big swing — a difference-maker who can start a deciding game of a playoff series.

The Fit

On paper, Cease would be a luxury signing. But this is the offseason to splurge.

Could the Cubs roll into 2026 with a rotation of Steele, Horton, Imanaga, Boyd, and Taillon? Absolutely. Would that group be good enough to win 90 games and make the playoffs again? Probably.

But if the goal is more than another Wild Card berth, this is where you upgrade. The Dodgers, Brewers, and Phillies all have frontline arms they can trust in October. The Cubs need one too.

Cease, Framber Valdez, or Ranger Suárez — any of them would represent the kind of “over-the-top” move that turns a playoff team into a contender. And after the injuries and late-season fatigue that plagued the 2025 rotation, Chicago could use that depth and reliability.

The Verdict

It just feels right.

Cease will be 30 on Opening Day, entering the prime of his career — and it would be poetic for that stretch to happen back in a Cubs uniform.

Steele, Imanaga, and Boyd give Chicago a lefty-heavy staff. Cease is the electric right-hander that perfectly balances the rotation. And the fact that the Cubs are already linked to him before free agency officially opens suggests Jed Hoyer might be gearing up for a serious pursuit.

Prediction: I love the fit. I think it happens. I'll say six years and $186 million.