The Chicago Cubs have been sending mixed signals in their offseason strategies, transitioning from bold moves to a more conservative approach. After firing David Ross and hiring Craig Counsell, the Cubs made some notable signings but failed to make significant roster additions.

This winter, they traded for Kyle Tucker from the Houston Astros but also let go of Cody Bellinger to the New York Yankees, raising eyebrows among fans. The Cubs' front office is focused on incremental improvements and balancing short-term success with future potential, as they aim to break a playoff drought that has lasted since 2018.

The Chicago Cubs concluded the 2024 season in a less favorable position compared to 2023, despite having the same record. This prompted significant offseason changes, starting with the signing of veteran pitcher Matthew Boyd to a two-year deal aimed at strengthening their rotation.

Boyd's impressive ERA of 2.72 in 2024 came from a limited number of innings, raising questions about his durability. The Cubs also executed a major trade, acquiring superstar Kyle Tucker from the Houston Astros, while parting with Isaac Paredes, Cam Smith, and Hayden Wesneski.

Additionally, the Cubs traded Cody Bellinger to the New York Yankees, freeing up payroll space. With a current payroll of $131.3 million, the Cubs are positioned to make further moves to enhance their competitiveness for the 2025 season, marking a promising offseason for the franchise.

The Chicago Cubs are actively enhancing their pitching staff this offseason, having traded for Eli Morgan and signed Phil Bickford. They also added veteran Matthew Boyd to strengthen the rotation.

While pursuing high-profile players, the Cubs are reportedly interested in Hoby Milner, a former Milwaukee Brewers pitcher, to bolster their bullpen. Manager Craig Counsell's connection to Milner could influence this potential move.