Craig Counsell left the Milwaukee Brewers primarily due to the opportunity for a new professional challenge and a groundbreaking contract offer from the Chicago Cubs. His contract with the Brewers expired, and the Cubs offered him a five-year deal worth $40 million, making him the highest-paid manager in Major League Baseball history. Counsell had expressed a desire for a change after dedicating nine seasons to managing the Brewers, a small-market team with budget constraints. Additionally, his family situation allowed him to commute from Milwaukee to Chicago easily, making the move feasible. The decision shocked many Brewers fans because Counsell was deeply connected to Milwaukee as a native and the most successful manager in Brewers history. His move to a division rival also fueled a sense of betrayal among supporters. However, Counsell indicated that the move was motivated by professional growth rather than finances alone. The Brewers had reportedly offered a contract to make him the highest-paid manager as well, but Counsell had already decided to pursue the new opportunity. Another significant factor that reportedly influenced Counsell's thinking to leave was the trade of star closer Josh Hader by the Brewers in 2022, which affected the clubhouse and his outlook on the team's direction. Overall, Counsell left Milwaukee to accept a highly lucrative contract and a fresh challenge, moving to the Cubs, which many saw as a dramatic and emotional shift given his local ties and legacy with the Brewers.