The Chicago Cubs made clear progress during the 2025 season. They finished with a 92-70 record, placing second in the National League Central and returning to the playoffs for the first time since 2020.
In the postseason, Chicago opened with a strong showing in the Wild Card round, defeating the San Diego Padres in a best-of-three series. Their run ended in the National League Division Series, where they were eliminated by the Milwaukee Brewers in five games. After falling behind 2-0 in the series, the Cubs managed to force a decisive Game 5, but ultimately lost the finale 3-1.
Despite the disappointing ending, the Cubs can feel encouraged by the overall results of their 2025 campaign. Reaching the postseason again was a major step forward, and the organization is now focused on building momentum heading into 2026.
With expectations rising, Chicago is aiming to significantly upgrade its roster this offseason. One of the biggest names connected to the Cubs has been star infielder Alex Bregman, and recent developments suggest that interest may be mutual.
Cubs Seen as Top Fit for Alex Bregman
In an article for The Athletic, Jim Bowden evaluated the best landing spots for the top free agents in baseball and identified the Cubs as the strongest fit for Bregman.
Bowden noted that Bregman is seeking a long-term deal similar to the contracts recently secured by Kyle Schwarber and Pete Alonso. According to Bowden, Chicago may offer Bregman his best chance at that kind of commitment, especially as the team looks to replace offensive production in its lineup. He also highlighted the Cubs’ appreciation for Bregman’s leadership and ability to mentor younger players. If signed, Chicago could shift Matt Shaw to second base, trade impending free agent Nico Hoerner, or move Shaw into the outfield.
Bregman’s on-field production supports the idea of a strong fit. He would give the Cubs another impactful right-handed bat, something the lineup could use. Last season with the Boston Red Sox, Bregman hit 18 home runs, drove in 62 runs, and posted a .273 batting average. He has also reached at least 23 home runs in five different MLB seasons.
Competition Remains for Bregman
Even if the Cubs are viewed as a top destination, they are far from alone in pursuing Bregman. Bowden also pointed to the Detroit Tigers and the Red Sox as logical suitors.
Detroit has been connected to Bregman for some time and could benefit from adding a proven star infielder. Meanwhile, Boston has reason to consider bringing him back after his strong performance last season, especially after missing out on other high-profile targets.