Cubs’ biggest offseason needs and who might actually fill them

The World Series is over, and the true start to the offseason has arrived. The Chicago Cubs were a victory away from reaching the NLCS, but the result of 2025 proved that the front office still has some work to do if they are going to be a legitimate contender in 2026. The Cubs have the prospect capital and financial flexibility to be among the most aggressive teams in baseball during the offseason, but that's a level of urgency the front office hasn't had since the team won the World Series in 2016.

The obvious need the Cubs have as free agency gets underway is for power pitching, both in their starting rotation and the bullpen. However, it can't be understated that the Cubs are expected to lose Kyle Tucker this offseason. While the Cubs may be ready for Owen Caissie to replace Tucker in right field, the team will need to find a way to replace the offensive production the All-Star outfielder had during the first half of 2025.

Who could fix the Cubs’ most glaring offseason problems?

Given how the Cubs have operated in recent years, it's not as easy as pointing to the top name available at the position they need and saying that they will sign that player. The Cubs will never act like the Los Angeles Dodgers or New York Mets.

Starting pitcher - Joe Ryan

Joe Ryan was among the controllable starting pitchers the Cubs checked in on at the MLB trade deadline. The Minnesota Twins had a fire sale at the deadline, and had they been afforded more time, they likely would have found a suitor for Ryan.

With two more years of arbitration, the financial cost of adding Ryan wouldn't rival the Cubs' spending on a top free-agent starting pitcher. The prospect cost would sting, but the top-heavy farm system the Cubs have has to be put to use in trade if the front office is not going to use free agency to address their biggest needs.

Replacing Kyle Tucker's offense - Alex Bregman

Replacing Tucker's offense is easier said than done. As much as Kyle Schwarber makes sense for the Cubs, it's hard to see Schwarber passing up on a return to the Philadelphia Phillies, especially since the Cubs won't be outbidding the Phillies. With the Cubs seemingly having their starting outfield set, bringing Cody Bellinger back doesn't make much sense either.

The guess here is that the Cubs make a strong push for Alex Bregman. The Cubs identified Bregman as the piece last offseason that could transition them from being a good team into a great team. They weren't wrong, but the problem was that the Cubs made a pursuit of Bregman a priority far too late in the offseason. The Boston Red Sox likely will make a strong push to bring Bregman back, but the Cubs being involved shouldn't be that surprising.

High-leverage relief pitcher - Devin Williams

Chances are the Cubs' bullpen is going to look quite different in 2026. It would seem that Daniel Palencia will be on the inside track for the closer's role, but most of the high-leverage relief pitchers Craig Counsell turned to in 2025 are free agents this winter.

It wouldn't be a complete shock to see the Cubs turn to Counsell's former bullpen ace with the Milwaukee Brewers, Devin Williams. Williams struggled in his only season away from the Brewers, and could be looking for a prove-it deal this offseason to replenish his stock. The Cubs make a ton of sense here.