By Nick Deeds | at
Free agency won’t officially begin until five days after the conclusion of the World Series, but teams are already well into the process of making their plans for the coming offseason. For many times, that will include pursuits of some of the winter’s top free agent talent. While Cubs outfielder Kyle Tucker is widely viewed as the top hitter headed into free agency this November, Bruce Levine of 670 The Score reported a connection between Chicago and one of the winter’s top pitchers: right-hander Dylan Cease. Levine reports that the Cubs are viewed as a potential top suitor for Cease and that he will be pursued by the North Siders this winter.
Cease has significant ties both to the city of Chicago and the Cubs organization as a whole. Drafted by the Cubs in the sixth-round of the 2014 draft, Cease developed into a top-100 prospect in the Cubs organization before being traded alongside Eloy Jimenez in the crosstown deal that brought Jose Quintana to Chicago prior to the 2017 trade deadine. While neither Jimenez nor Quintana quite lived up to expectations during their stints with their new clubs, Cease turned into the sort of top-of-the-rotation arm the White Sox were surely dreaming of when they made the trade. He was the runner-up for the AL Cy Young award with the South Siders in 2022 in his age-26 season and was traded to the Padres just before the start of the 2024 campaign for a package headlined by top pitching prospect Drew Thorpe.
2024 saw Cease put together another ace-level campaign as he pitched to a 3.47 ERA in 33 starts while striking out 29.4% of his opponents. He finished fourth in NL Cy Young award voting and even garnered some down-ballot MVP consideration. That seemed to set up Cease up for a major payday in free agency as long as he could keep it up in 2025, but he stumbled this year with a rather pedestrian 4.55 ERA in 168 innings of work. Cease’s peripherals were a good deal better than his results suggested, but a tough 2025 season creates a pattern of inconsistency that might worry some suitors after a similarly pedestrian 2023.
Cease might lack the sort of year-to-year consistency many clubs look for when searching for an ace to carry their pitching staff, but it’s still easy to see why he would be attractive to teams. The right-hander has been one of the game’s most durable arms in recent years, and his peripherals have remained far more consistent than his actual results. He’s struck out at least 200 batters in five consecutive seasons with at least 32 starts and a 165 innings in each of those seasons. While his ERA has fluctuated between 2.20 and 4.58 across those five seasons, his FIP (between 3.10 and 3.72) and SIERA (between 3.46 and 4.10) have been far more stable. While Cease’s 3.72 ERA ranks 29th among starters with at least 500 innings of work since 2021, his FIP (12th), SIERA (22nd), and xERA (11th) all rank more favorably.
Perhaps most importantly for the Cubs specifically, Cease throws hard and racks up strikeouts. His strikeout rate ranks 3rd in that aforementioned group, behind only Blake Snell and Gerrit Cole. His fastball velocity, likewise, ranks third behind Cole and Sandy Alcantara in that same group. Cease actually threw harder than his career average this year with a 97.1 mph fastball velocity. That was good for sixth among qualified starters this season, and his strikeout rate trailed on Tarik Skubal and Garrett Crochet. For a Cubs rotation that had the third-lowest fastball velocity in the majors at just 93.1 and put together a pedestrian 20.5% strikeout rate, Cease would be the sort of power pitcher a generally soft-tossing Cubs rotation could really benefit from.
As good of a fit for the Cubs as Cease might seem to be on paper, that shouldn’t be taken to mean a deal is necessarily likely to get done. Cease will have plenty of suitors as one of the top starters on the market, and big spenders like the Mets are known to be in the market for rotation help this winter. Cease’s familiarity with the Cubs organization and the city of Chicago is unlikely to give the Cubs a significant leg up considering that Cease is a client of the Boras Corporation, and agent Scott Boras’s clients aren’t known for affording much of a hometown discount in free agency.
The Cubs haven’t spent at the top of the free agent market very often in recent years. Since signing Jon Lester and Jason Heyward in back-to-back offseasons in 2014 and ’15, the Cubs have signed just two players to deals worth $100MM or more: Yu Darvish, who was famously traded to the Padres halfway through his six-year, $126MM pact with Chicago, and Dansby Swanson. Cease will surely be seeking a contract worth at least that much, and it’s unclear if the Cubs would be willing to go out of their comfort zone to land him.
Another factor could be the Qualifying Offer, as the Cubs have generally been reluctant to sign qualified free agents. Swanson is the only free agent Chicago has signed with a QO attached outside of re-signing their own players since they signed John Lackey to a two-year deal in December of 2015. Even if the Cubs aren’t interested in playing at the top of the market, it’s at least possible that they would circle back to Cease later this offseason if his market doesn’t materialize, as they did with Cody Bellinger during the 2023-24 offseason and attempted to do with Alex Bregman last winter.
It’s also worth wondering whether adding a starting pitcher will be the team’s top priority this winter to begin with. Whether they pursue a reunion with Tucker or not, targeting a bat in free agency could make some sense given that the club’s internal options to replace him in the lineup would be unproven prospects Moises Ballesteros, Owen Caissie, and Kevin Alcantara. The bullpen might also be a priority given that every high leverage reliever from this year’s relief corps except Daniel Palencia is scheduled to hit free agency this winter.
Of course, starting pitching could become a larger priority for the club in a hurry depending on how the option decisions between the club and southpaw Shota Imanaga play out in the coming days. Imanaga departing for free agency would create some urgency to replace him in the rotation, while him remaining in the fold alongside Jameson Taillon, Matthew Boyd, and Cade Horton with Justin Steele expected back from surgery in the first half of next season could be enough rotation talent to convince the Cubs to prioritize improving other areas of the roster. Colin Rea’s bargain $6MM club option for 2025 is likely to be picked up, and he’ll join Javier Assad as quality depth for the Cubs rotation headed into next year beyond their on-paper starting five.
