The Chicago Cubs are gearing up for a promising 2025 season following a transformative offseason. After missing the postseason for two consecutive years despite solid records, the Cubs made significant moves to enhance their roster. The acquisition of Kyle Tucker from the Houston Astros brings elite talent to the outfield, while Ryan Pressly’s addition aims to solidify a previously shaky bullpen. Chicago's interest in Alex Bregman showcases a continued commitment to improvement.

Moreover, the Cubs are looking to bolster their pitching rotation, with Jordan Montgomery emerging as a potential target. After a rough season with the Arizona Diamondbacks, where he posted a 6.23 ERA, Montgomery rebounded well with the St. Louis Cardinals and Texas Rangers, finishing the 2024 season with a 3.20 ERA and playing a crucial role in the Rangers' World Series victory. The Cubs see acquiring Montgomery as a low-risk, high-reward strategy to deepen their rotation and prepare for potential postseason play.