4 Cubs targets likely to come off the board fast at the 2025 Winter Meetings

With the Winter Meetings taking place next week, there should be an uptick in rumors surrounding the Chicago Cubs as they look to address their biggest need of the offseason: adding a top-of-the-rotation starting pitcher. A goal at which the Cubs appear to be at a crossroads in their attempt to accomplish it.

To the surprise of no one, reporting after the fact confirmed that the Cubs were involved in the bidding for Dylan Cease but bowed out once the offer from the Toronto Blue Jays surpassed $200 million. It's hard to find a silver lining in that reporting, considering that it is the space the Cubs have been living in since 2019. However, in adding additional context, The Athletic's Patrick Mooney and Sahadev are, at least, saying there's a chance the Cubs sign a pitcher to a nine-figure deal this offseason.

4 Cubs targets likely to come off the board fast at the 2025 Winter Meetings

The premise is that the fact that the Cubs were even involved in the bidding for Cease at this stage of the offseason would offer some sense that the front office should be active at the Winter Meetings. Time will tell, but as the offseason's tentpole even often proves, once one move happens, potential targets could come off the board quickly.

• Michael King

Michael King may not land the largest deal, among free-agent starting pitchers, at the Winter Meetings, but he could be one of the first to sign. Framber Valdez and Ranger Suarez, given their durability, could fetch more, but King's high ceiling could see teams move to bring him in as soon as possible. The Cubs will likely be among those teams, and if the free-agent market is the primary method with which they address their need in the rotation, King feels like the obvious selection.

• Tatsuya Imai

Timing sort of dictates Tatsuya Imai deciding at the Winter Meetings or within days after. Imai's posting window closes the first week of January, and with teams usually entering a lull to close out the calendar year, it would make sense for Imai to sign next week. Imai is one of the youngest options on the free-agent market, and for a team like the Cubs, their preference could be to spend on a future projection like his, as opposed to throwing money at a veteran approaching the wrong side of 30.

• Brad Keller

Given the success Brad Keller had in the Chicago Cubs' bullpen last season, he figures to be a popular name at the Winter Meetings. When the offseason started, and the impression was that the Cubs weren't going to be signing any reliever to a multi-year deal, Keller's return to Chicago felt unlikely. Now, with the Cubs looking to add another established arm after signing Phil Maton, Keller's return could be in the cards.

• Alex Bregman

Given that Alex Bregman is represented by Scott Boras, never say never, but it doesn't feel like Bregman's free agency will have the same charade it did last year, when it extended until the start of spring training. The Cubs are likely keeping tabs on Bregman, with the idea that he represents a clear upgrade for their offense at a position they could use one, but the Boston Red Sox may act quickly to bring him back--especially after addressing their rotation need with the trade for Sonny Gray last month.