San Diego Padres starting pitcher Dylan Cease works against a Milwaukee Brewers batter during the first inning of a baseball game Wednesday, Sept. 24, 2025, in San Diego. (AP Photo/Gregory Bull)
Copyright 2025 The Associated Press. All rights reserved
Starting pitcher Dylan Cease is set to be an unrestricted free agent this winter after two seasons with the Padres, and it is almost certain that a number of teams will be vying to sign him. Cease will be entering his age-30 season in 2026, so this will represent his last chance to get a top-dollar contract. Though 2025 was something of a down year for Cease, he should still be one of the most sought-after arms on the market.
One team that has already been specifically linked to Cease is the Chicago Cubs. On October 25, Bruce Levine of Chicago’s 670 AM sports radio reported a connection between Cease and the Cubs. There has not been a lot of speculation beyond that, but because free agency can’t officially begin until next week, there is also not much reason to expect hot stove talk.
That said, the Cubs make a lot of sense as a landing spot for Cease. They are coming off of a successful season in which they improved their regular season win total by 9 games over the past two years and reached the playoffs for the first time since 2020, so the Cubs should be expected to be looking to keep getting better. One of the major steps in that process will be signing outfielder Kyle Tucker to a long term deal, and along with that, the Cubs will likely be working to bolster their pitching staff.
The starting rotation combined for 10.3 fWAR in 2025, and that was without Justin Steele, who went down in April with an elbow injury that required Tommy John surgery. That wins above replacement total of 10.3 was good for 17th in baseball, which means the Cubs have plenty of room for improvement.
Cease would be a great fit for the Cubs in that regard. Even in an off year, Cease was good for 3.4 wins above replacement in 2025, which matches the Cubs’ leader among starters, Matt Boyd. Cease has demonstrated during his career that he will have some ups and downs, and when those peaks come, he can help carry a pitching staff. In 2024, for example, Cease was good for almost five wins above replacement, and in 2021 and 2022, he had fWAR totals well above four.
It’s clear that Cease would make the Cubs better. They should have a solid starting pitching staff going into 2026, but adding Cease to the mix would give heft to the middle of the rotation. The Cubs might have missed on improving enough at the July trade deadline, and that decision may have contributed to falling short against the Brewers in the division series earlier this month, but they have a chance to right that ship this winter.
The primary question with Cease might come down to cost. The Cubs are projected to be about $94 million below the luxury tax threshold in 2026, according to Spotrac, and with more money coming off of the books in the years after that as the contracts of players like Seiya Suzuki and Ian Happ expire, signing Cease to a multi-year deal should be easily done, at least financially.
Cease would come to the Cubs with existing ties to the city of Chicago and the Cubs organization. Cease was originally drafted by the Cubs and was rising through their farm system when he was a part of the 2017 trade for Jose Quintana that sent Cease to the White Sox. Cease debuted with the Sox in 2019 and was a part of their 2020 and 2021 playoff teams before they traded him to San Diego in March of 2024.
Whether that would make Cease more apt to return to Chicago is not certain, but the familiarity of both the city and the Cubs organization could realistically play a role in Cease’s decision when he weighs the offers coming in from different teams.
There is little question that Cease has many of the qualities in a starting pitcher the Cubs are in the market for. He has started at least 30 games in each of the last five seasons, and even in off years, Cease logs high strikeout totals. In 168 innings pitched last season, Cease had 215 strikeouts. And in each of the past five years, Cease has never had a strikeout total lower than 214. In short, the man is a strikeout machine, something the Cubs could badly use, as they ranked 24th in baseball in strikeouts in 2025.
In all, Dylan Cease is easily a good fit for the Cubs. A return to that organization makes a lot of sense, both for them and for him as a pitcher. There will undoubtedly be a few offers coming his way, and the question might be whether the Cubs field one that is competitive enough and whether Cease thinks coming back to Chicago is something that will benefit his career.