Cubs Eye Reunion With Dylan Cease as Free Agency Looms

The Chicago Cubs are targeting Dylan Cease to strengthen their roster. Find out what this means for the upcoming offseason.

The Chicago Cubs are expected to make a strong push for right-hander Dylan Cease this offseason, according to Bruce Levine of 670 The Score, as the team looks to add a power arm to its rotation.

The move paid dividends for the White Sox, as Cease became a Cy Young runner-up in 2022 before being dealt to San Diego prior to the 2024 season.

What Cease Brings

Despite a down 2025 season with a 4.55 ERA, Cease remains an attractive option for teams seeking rotation help. His underlying metrics suggest better performance than his surface numbers indicate, and he brings exactly what the Cubs’ rotation lacks: power and strikeouts.

Story continues below.

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Cease has struck out at least 200 batters in five consecutive seasons while making at least 32 starts each year.

Challenges Ahead

Landing Cease won’t be simple. As a Scott Boras client, he’s unlikely to offer any hometown discount to his former club, and he’ll likely command a contract worth at least $100 million. The Cubs have been hesitant to spend at the top of the free-agent market in recent years, with only Yu Darvish and Dansby Swanson receiving nine-figure deals since 2015.

Additionally, Cease will likely receive a qualifying offer from San Diego, and the Cubs have historically avoided signing qualified free agents, with Swanson being the lone exception in nearly a decade.

Rotation Priorities

The Cubs’ pursuit of Cease may depend on whether Shota Imanaga exercises his opt-out clause. If Imanaga departs, adding a front-line starter becomes more urgent. If he stays alongside Jameson Taillon, Matthew Boyd, and promising rookie Cade Horton, the Cubs might prioritize other areas.

With Justin Steele expected back from surgery and Colin Rea’s option likely to be picked up, the Cubs have rotation depth—but they lack the high-velocity, strikeout pitcher that Cease represents.

For a team looking to take the next step in the competitive NL Central, reuniting with their former prospect could be the perfect move.