No matter how you slice it, the Chicago Cubs were one of the most disappointing teams of 2024. Improved play in the second half enabled a winning record and a second-place finish in the NL Central, but the Cubs finished six games out of a wild-card spot and a whopping 10 games behind the rival Brewers. At this time a year ago — before our collective focus shifted to star players such as Shohei Ohtani and Juan Soto — the baseball industry was in shock following the Cubs’ ultra-aggressive maneuver to hire manager Craig Counsell away from Milwaukee with a five-year, $40 million deal, the largest contract ever given to a big-league skipper.
That Milwaukee then ran away with the division while the Cubs were stuck in the mud for much of Counsell’s first season at the helm only made Chicago’s uninspiring campaign that much more frustrating. The Cubs have not reached the postseason since Jed Hoyer assumed the top front office role after Theo Epstein departed following the 2020 season, and they haven't won a postseason game since 2017. Considering the talent on the roster and the massive commitment made to Counsell, such shortcomings can be tolerated for only so much longer.
This organization must find a way to reestablish itself as a legitimate contender in the National League, and quickly. Here are the five biggest questions facing the Cubs this winter. “Anytime a really good player decides to stay with you, that's good news,” Hoyer this month after Bellinger’s decis.