Cubs Appear to Be Plotting Two Main Paths Forward This Winter

This is essentially a reiteration or clarification of some of the ideas we’ve been discussing for a while now, but it seemed worthwhile to revisit them while we wait for further developments. The Cubs appear to be plotting two potential paths, with January 2 looming as the divergence. That’s when Japanese righty Tatsuya Imai has to make a decision on his new team, and the Cubs remain in the hunt by all accounts.

Pitching has been Jed Hoyer’s priority this winter, and he’s done a pretty good job of adding to the bullpen without spending much on it. Now comes the rotation, which could really use both depth and a higher ceiling. The 27-year-old Imai would check both of those boxes while giving the Cubs a controllable starter they can build around when several other contracts fall off the books after this season.

“I would say the feel-good part of signing Imai for the Cubs, along with the baseball smartness of the deal, is pretty equal,” Bruce Levine said on 670 The Score’s Inside the Clubhouse on Saturday morning. “If the Cubs come out of the winter here and they’ve signed Imai, they haven’t added another hitter to replace Tucker, I think they’re gonna be alright.

“Because you have the young hitting options in Ballesteros and Caissie to go along with what you already have in Suzuki kind of reinventing himself as a right fielder again last year when Tucker was out.”

Imai is projected to command around $25 million annually, which would take a big bite out of the roughly $40 million the Cubs have left under the first luxury tax penalty level. So unless Tom Ricketts is willing to green-light a lot more spending, which is possible given how much payroll falls off after 2026, there would be no more big additions. But if Imai goes elsewhere, the Cubs are going to have to pivot.

Rather than paying big for Framber Valdez or Ranger Suárez, they might choose to make a big splash for a position player.

“The Cubs have had many conversations with Scott Boras about Alex Bregman,” Levine noted.

The Blue Jays and Diamondbacks are also in the mix, with other recent reports characterizing Arizona’s interest as being very legitimate. If the Cubs were to make the winning bid for Bregman, they’d be eating up even more of that presumed budget. That means their only avenue to improve the rotation would come via trade, and a pair of Marlins have been mentioned frequently since at least the trade deadline.

“The Cubs have been after (Sandy) Alcántara and, more recently, Edward Cabrera a lot,” Levine said. “So instead of signing Imai, might they be going in the direction of, ‘We’re going to trade some of our inventory for Alcántara or Cabrera and then have another pitcher and some of our younger inventory from our minor leagues available to be able to make other trades or spend our last $30-40 million on a player like Bregman at third base.”

Alcantara’s $11.02 million AAV looks incredibly reasonable, but adding his salary to Bregman’s would still push the Cubs over into penalty range. What’s more, that AAV would actually jump by over $6 million because a trade would reset it to what is remaining on the deal. The Cubs would also have a $21 million option for 2027, though the uncertainty of that season creates a little unease.

Cabrera is almost three years younger and is under control for three years via arbitration, which will make him significantly cheaper for the next two years. Even that final arb year shouldn’t reach quite with Alcántara would be owed. That also means Cabrera will cost a lot more in terms of the player/prospect return, but such a deal would be easier to swallow when the Cubs would have three seasons of control.

Having Bregman in the fold provides a good deal of leeway when it comes to moving prospects as well. Of course, there’s still a ton of gray area because it’s not as simple as just saying the Cubs will land either Imai or Bregman. It’s more a matter of those two looking like their most likely big swings, after which the rest of the pieces will sort of fall into place.

Or rather, what happens with those two big names will determine Hoyer’s willingness to spend from his payroll and/or prospects. Having the ability to go over the first penalty could see the Cubs targeting more Imai and utility infielder Kazuma Okomoto, or it could mean getting Bregman and Alcántara. Levine teased an Imai/Bregman combo, but dropping $50-60 million on two players doesn’t seem to be in the cards. Unless Hoyer and Ricketts have been reading Bobby Frost, that is.

We’re down to a week left on Imai’s clock, and it’s hard to imagine Bregman signing before then. Both are Scott Boras clients, so the super-agent probably wants to conclude the more pressing set of negotiations before moving on. And if the Cubs are truly involved on both fronts, he knows he can keep them on the hook that much longer.

I’m interested in hearing what you all think is the most likely scenario, though I’d imagine the general public will go with the option that sees neither Bregman nor Imai on the North Side. Drop a line in the comments so we can discuss further which way you think the Cubs will go.

A) Sign Imai, add low/mid position player
2) Sign Bregman, trade for controllable starter
D) Sign neither, settle for fallbacks
X) Other (share specifics)

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