Cubs expected to pursue a former Cy Young finalist in free agency

The Chicago Cubs may be about to take a big swing for their rotation.

Chicago is expected to pursue San Diego Padres pitcher Dylan Cease in free agency this winter, Bruce Levine of 670 The Score reported this week. According to Levine, the Cubs are seen as a potential top suitor for Cease.

The right-hander Cease, 29, is considered to be one of the marquee arms on the free agent market. He just posted his fifth consecutive season with 200 or more strikeouts and also was the AL Cy Young runner-up with the Chicago White Sox back in 2022.

Cease was a little bit volatile though in 2025, posting an 8-12 record with a 4.55 ERA and a 1.33 WHIP. While his swing-and-miss stuff is still some of the best in baseball, Cease was more prone this year to walks as well as overall hard contact.

For the Cubs, they relied heavily this season on the likes of Matthew Boyd (34), Jameson Taillon (33), and Shota Imanaga (32) in their rotation. When those pitchers struggled, especially during the NLDS against the Milwaukee Brewers, Chicago’s title hopes came undone.

Cease is younger than all of those guys and may come at a slight discount given the up-and-down season he just had for the Padres. Still, it is very possible that the Cubs could face some heavy competition for Cease’s services as the seven-year MLB veteran was heavily pursued by some major teams at this year’s trade deadline (before ultimately staying put in San Diego).

H/T MLB Trade Rumors

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