Cubs' Biggest Misses of Winter to Date Came This Weekend. Can They Find the Right Alternatives?

Other than players like Shohei Ohtani and Juan Soto, it's a little silly to fixate on any one free agent, from a fan perspective. The likelihood of landing that particular player is quite low, because (after all) the players in question are free to choose the team they prefer. For reasons financial, geographic, competitive or personal, plenty of players end up going somewhere else, even though they seemed like a great fit for the team. Getting upset each time that happens is a recipe for perpetual hot stove misery, and the point of the hot stove season is fun, not misery.

Eventually, though, a team does have to find the best player and value they can, and act on it. Sit and watch too long, and good lanes close up for you. The good solutions to obvious problems grow thin, and the few still available become more costly, because the agents or team executives involved begin to sense that they can apply leverage in negotiations. After a flurry of moves this weekend, the Cubs might be approaching that territory—though it would be too much to suggest that they're there already.

The Mets signed Clay Holmes to a three-year, $38-million contract Friday night. That was a tough break for the Cubs, and a good example of the phenomenon above, because the Mets intend to move Holmes to the starting rotation. That would have made it practically impossible for the Cubs to rationally match New York's offer, because Holmes (while a fine candidate for that increasingly popular conversion) was not a great fit for the Cubs' projected starting rotation. They couldn't do much to prevent missing out on Holmes. Nonetheless, it was a bitter pill to swallow, because Holmes was one of the best candidates for the bullpen upgrade the team clearly needs this winter. Losing out on him unavoidably reduces the number of good options available to the team, in one area in which that list was already a bit short. There are rumors that they're interested in Kirby Yates, who could be a great short-term fix, but if Holmes hadn't gotten a big offer to switch roles, he could have shored up the back of the Cubs pen through 2027.

On Sunday, the market gave the Cubs another 1-2 punch to the proverbial gut, as Tyler O'Neill and Michael Conforto each signed reasonably-priced deals. O'Neill will make just under $50 million over the next three years with the Orioles, while Conforto—one of my favorite targets for the team should they trade Cody Bellinger, after he had a season in which his superficial stats failed to keep up with good batted-ball data and especially impressive bat-tracking numbers—landed with the dynastic Dodgers on a one-year deal that didn't even reach $20 million. That's this winter's answer to last year's Teoscar Hernández signing for Los Angeles, and another painful miss for the Cubs.

Realistically, the team almost certainly felt like they couldn't sign a player like Conforto or O'Neill before trading Bellinger. Again, that would have put them in a tough position to deal with either teams or free agents, because the whole industry is aware of the self-defeating limits being placed on the team's spending by ownership and acquiesced to by their insufficiently assertive front office. Still, the missed opportunities are real.

There are still plenty of ways the team can try to improve themselves, overall, even if and when they trade Bellinger. The number of viable options dwindled this weekend, though, and whereas it might have been easy to shrug off misses on players like Willy Adames or Shane Bieber due to their cost and fit on the roster, a few players who went elsewhere most recently cut deeper. Jed Hoyer faces a stern test, and Conforto, especially, would have gone a good distance toward helping him pass it. Instead, he'll have to thread the needle from a different angle.