Even when the Chicago Cubs have a successful season, there is usually a “but” that follows it. For more than 100 years, the “but” was not winning the World Series. Now, after amassing 92 wins and returning to the playoffs in a full 162-game campaign for the first time since 2018, there should be a feeling of hope suffusing the North Side. The Cubbies are theoretically positioned for a prosperous run in the National League…. but fans are skeptical ahead of Winter Meetings.
The Tom Ricketts-owned ballclub has an abundance of free agents this offseason, with Kyle Tucker and Shota Imanaga headlining the group. Fostering growth can be difficult without continuity. The expectation around the league is that Chicago will lose its All-Star outfielder to the highest bidder, but (it can have a positive connotation as well), the front office is positioned to make a big move elsewhere.
“The Chicago Cubs know that finishing second to the Milwaukee Brewers in the NL Central every year is inexcusable, and with Tucker expected to depart for greater riches, they’ll have plenty of money to burn,” USA Today's Bob Nightengale writes. “They want another corner outfielder, and will be shopping in the expensive aisle for starting pitching, with fellow {general managers} predicting they could land Framber Valdez and/or Dylan Cease.”
Fans will not tolerate inaction. While they may accept moving on from Tucker, who did blend into the background during the second half of the 2025 campaign, at least one notable addition is expected. Retaining a solid starting rotation is vital, especially if Imanaga joins another squad.
Do the Cubs have their eye on a prominent hurler?
Valdez and Cease each come with question marks, but they also offer plenty of appeal. Before faltering down the stretch last season, the former had earned the reputation of being one of the most consistent left-handers in the league. He posted a 3.36 ERA in 188 games with the Houston Astros and has logged 190-plus innings in three of the last four years. Though, the Cubs may have to carefully consider possible character concerns after Valdez crossed up catcher Cesar Salazar in September.
Cease is more erratic on the mound, recording a 4.50-plus-ERA twice in the last three campaigns and owning a 10.0 percent career walk rate. However, few hurlers possess more firepower than the 29-year-old righty. He has eclipsed 200 strikeouts in four consecutive seasons and boasts two top-five Cy Young finishes. Teams covet swing-and-miss stuff, specifically for the playoffs, so he should command a fair amount of interest.
Chicago president of baseball operations Jed Hoyer will presumably take a look at these two free agents and other front-line starting pitchers this winter. Ultimately, though, it will take Ricketts' seal of approval for the Cubs to put together the huge offseason the city is demanding.
