The Chicago Cubs are entering the offseason facing critical decisions regarding player acquisitions and potential extensions after a 2025 season that saw them break their postseason drought but ultimately fall short against the Milwaukee Brewers in the NLDS [9]. The team's focus is now on re-tooling to make a deeper playoff run next season [5].
Key Player Decisions and Potential Acquisitions
One of the biggest questions looming over the Cubs is what to do with Kyle Tucker, who is heading into free agency [1, 3]. The Cubs traded two talented young players to acquire Tucker as a rental last offseason, and while he performed well in Chicago, his future with the team remains uncertain [3]. Meanwhile, the Cubs have seemingly removed themselves from the Shohei Ohtani sweepstakes [4, 5]. The team wasn't willing to budge on the deferred money deal that Ohtani eventually agreed to, suggesting he was always leaning towards the Dodgers [4].
However, the Cubs may consider pursuing Dylan Cease, currently a starting pitcher for the San Diego Padres [7]. Cease has existing ties to the city and the Cubs organization, as he was originally drafted by the Cubs and later traded in 2017 for Jose Quintana [6]. Signing Cease to a multi-year deal should be financially feasible in the coming years, especially as contracts of players like Seiya Suzuki and Ian Happ expire [6]. The Cubs are also looking at potential free-agent fits, including standouts from other teams [2].
Extension Talks and Roster Stability
The Cubs may also consider extending Ian Happ's contract [11]. Happ has been a consistent player for the franchise and a mainstay in left field [11]. An extension would keep him around and potentially allow him to reach 200 career home runs for the Cubs [10]. Despite experiencing slumps, Happ has shown the ability to go on tremendous hot streaks, making him a valuable asset to the team [10].
Looking back at the 2025 season, Willi Castro, acquired from the Twins at the deadline, struggled in the second half [8]. On a positive note, Palencia stepped up as closer, notching 22 saves after taking over the role from Ryan Pressly [8]. The Cubs' offense ranked in the top half of the league overall, but their performance dipped in the second half, finishing 16th in OPS (.721) and 20th in runs scored (281) [8].
TL;DR
* The Cubs face a critical offseason, deciding whether to re-sign Kyle Tucker and exploring other free-agent options [3]. * Chicago has apparently bowed out of the Shohei Ohtani pursuit [5]. * Dylan Cease could be a potential target, given his ties to the organization and the city [6]. * An extension for Ian Happ is on the table, recognizing his consistency and value to the team [11].