3 offseason goals the Cubs front office must complete by Opening Day

The Chicago Cubs made the playoffs this past season for the first time since 2020, ultimately bowing out to the division rival Milwaukee Brewers in the NLDS. With 2026 in mind, here are three areas the Cubs need to improve on in order to advance further.

3 areas the Cubs need to address to be competitive in 2026

Bolster the rotation

The Cubs found themselves scrambling at season’s end, as several of their starting pitchers were either sidelined due to injury or experienced regression. While Cade Horton established himself as a potential ace of the future, both Shota Imanaga and Matthew Boyd failed to maintain their early season form. Imanaga, in particular, gave up 18 home runs in his final 11 starts of the season including the postseason, making him a liability on the mound in the season's late stages. 

Imanaga returns to the Cubs in 2026 after accepting the team's qualifying offer and Justin Steele is set to rejoin the fold after missing almost all of 2025 with an elbow injury. If healthy, these two will provide a steady boost to the rotation, but the Cubs need a true top of the line ace if they want to go deep into next October. 

Establish a plan in the outfield 

Barring a miracle, Kyle Tucker is gone. Tucker declined the Cubs’ qualifying offer and is destined to chase a salary far above what Chicago is willing to offer. After holding on to him at the trade deadline, Owen Caissie looks to be the heir apparent in right field, but he’s, well, not Kyle Tucker. In an albeit small sample size of 12 games, Caissie batted .192 with just two extra base hits, leaving questions on whether he can fill the void left by Tucker.

The other alternative from within would be to move Seiya Suzuki back to the outfield and run Moises Ballesteros as the full-time DH, which would bring Suzuki’s defensive liabilities back into play. The other option would be to explore options externally (reunite with an old friend perhaps?) either in free agency or by trade. Both Caissie and Kevin Alcantara are still valuable chips should the Cubs decide to make a splash on the trade market.

Tighten up the infield depth

Last offseason, the Cubs appeared to be one of the front runners for free agent third baseman Alex Bregman, but never pulled the trigger. Bregman eventually signed with the Boston Red Sox, and the Cubs began the season with top prospect Matt Shaw manning the hot corner. While Shaw opened the season with a slow start, he proved he could be a valuable piece of the future, accumulating 3.1 bWAR with 13 home runs along with stellar defense throughout his debut campaign.

Still, the Cubs have a chance to rebound on last year’s whiff, as Bregman opted out of his three-year deal with the Red Sox, placing him back on the market once again. Even with a second half slump, Bregman finished the year with a more than respectable 128 OPS+, immediately making him the top third baseman on the free agent market. The Cubs are set to lose a huge part of their offense with Tucker’s departure, and could be inclined to lean towards proven offense and let Shaw develop in more of a utility role.