The Chicago Cubs, per very early reports, are targeting front-of-rotation pitching this offseason. Specifically, they have their eyes on the San Diego Padres’ hard-throwing right-hander Dylan Cease, according to various media reports.
More News: Chicago Cubs: Will Japan loom large in Cubs’ 2026 plans?
Cease, who turns 30 on December 28, will officially become a free agent shortly after the World Series and is expected to move on from the Padres in search of greener pastures and a more lucrative contract.
The question is whether the Cubs would be that team to provide the payday he’s expected to command (estimated at $158 million over six years by Spotrac), especially with plenty of other teams also looking to add a high-end starter heading into 2026.
Chicago Cubs have legit interest in Dylan Cease
Sep 18, 2024; San Diego, California, USA; San Diego Padres starting pitcher Dylan Cease (84) is congratulated in the dugout after a pitching change in the ninth inning against the Houston Astros at Petco Park. Mandatory Credit: Orlando Ramirez-Imagn Images
More News: Will the Chicago Cubs move on from Matt Shaw in 2026?
MLB insider Bruce Levin feels that, at the very least, the Cubs are in the running and considered a top contender for the services of their former top prospect, who they traded to the White Sox back in 2017.
“According to MLB insiders I know, people in the know in other organizations, they feel the Cubs will be there among the top suitors (for Dylan Cease),” Levine said during an interview with 670 the Score. “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.”
On the surface, this reported interest in Cease flies in the face of what would normally be expected of Cubs ownership and the front office. Chicago has shied away from big-ticket free agent starting pitching since signing Yu Darvish to a multi-year contract in 2018.
The Cubs’ current rotation seems already set from one to five, with Matthew Boyd, Shota Imanaga, Jameson Taillon, Cade Horton, and a returning Justin Steele. Colin Rea and Javier Assad will also be around as backup.
But, realistically, there’s a great deal of uncertainty when it comes their starting five.
Starting pitching concerns
Oct 1, 2025; Chicago, Illinois, USA; Chicago Cubs relief pitcher Shota Imanaga (18) reacts after giving up a two-run home run in the fifth inning against the San Diego Padres during game two of the Wildcard round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images
The Cubs still have to decide whether to pick up their option on Imanaga, who faded considerably as last season progressed and collapsed completely in the postseason. Boyd had a remarkable bounce back season after a long stretch of injury, but he also began to fade late in the season. There’s considerable concern that he’ll experience some degree of regression this coming season. Horton was a surprise breakthrough asset and, arguably, the best pitcher in all of baseball through the second half of 2025. However, the rookie has a history of injury and missed the final days of the regular season, along with the entire postseason, due to another physical setback. And when it comes to Steele, there’s no guarantee when, exactly, he’ll come back from his elbow surgery and whether he’ll be as dependable as he’s been in previous years.
Chicago also needs to take into consideration that Taillon and Boyd will become free agents at the end of the 2026 season, along with Rea.
So, it does make sense for the team to lock in an elite-tier starting pitcher who will be a guaranteed presence for this coming season and beyond.
But will Cease be that guy?
Bringing Cease aboard?
Oct 5, 2024; Los Angeles, California, USA; San Diego Padres pitcher Dylan Cease (84) throws a pitch in the second inning against the Los Angeles Dodgers during game one of the NLDS for the 2024 MLB Playoffs at Dodger Stadium. Mandatory Credit: Kiyoshi Mio-Imagn Images
That depends on a lot of things. Money will be an issue, even though Chicago is in a good position to be buyers this offseason. But a power-throwing righty would sure look good sandwiched between softer-throwing, more nuanced pitchers like Boyd and Imanaga. It would also be nice to carry an elite arm into postseason play when/if the Cubs make the playoffs again.
Cease is due for a better season this year after posting a 4.55 ERA in 2025. His velocity hasn’t dipped and his stuff remains solid. He also has the odd quirk of delivering better results in even-numbered years, which shouldn’t mean much of anything to the analytics-driven Cubs, anyway (Cease posted an average ERA of 4.53 ERA in 2019, 2021, 2023, and 2025 while notching an average ERA of 3.00 in 2020, 2022, and 2024).
But, most of all, adding Cease would mean adding another top arm to the front of the Cubs rotation. And, as we’ve all learned, a playoff-serious team can never have too much pitching.
Forgotten costs of free agency could steer Cubs’ offseason
Read More
For More Great Chicago Sports Content
Get the latest Chicago sports news, analysis, and breaking stories on the Bears, Bulls, Blackhawks, Cubs, White Sox, Sky, and more! Tap the star to add us to your favorites on Google News, so you never miss a story on your favorite Chicago teams.
Follow us on Twitter at @chicitysports23 for more great content. We appreciate you taking time to read our articles. To interact more with our community and keep up to date on the latest in Chicago sports news, JOIN OUR FREE FACEBOOK GROUP by CLICKING HERE