Those nagging doubts were magnified by heightened expectations. After the thrill of 2016, anything short of a dynasty felt like a disappointment, fairly or not. The 2017 Cubs won 92 games and advanced to a third consecutive National League Championship Series—yet the dominant narrative was that the Cubs had suffered from a “championship hangover”; 2018 was similar. The Cubs won 95 games, tied for the most in the National League, but abruptly ended their season with back-to-back losses in the divisional tiebreaker and Wild Card games. Epstein declared that the team’s offense “broke” and announced that Maddon would manage the final season of his contract without an extension.
By then, Maddon had become the preferred target for Cubs fans’ frustrations and media second-guessing. His reputation as a “players’ coach,” once his greatest strength, was recast as a liability, especially when several of the Cubs’ no-longer-quite-so-young players stalled or regressed in their development. The 2019 Cubs reinforced that narrative, producing results that were “less than the sum of the parts” of their roster. (A manager certainly deserves some blame for such extreme inconsistency, but other factors were beyond Maddon’s control: poor free-agency decisions by the front office, a key veteran’s months-long personal leave, a rash of post–All-Star–break injuries suffered by star players.) Despite the struggles, the Cubs stayed in contention for a fifth straight postseason berth—until a brutal nine-game September losing streak knocked them out of the playoff race and sealed Maddon’s fate.
In their joint press conference on the season’s last day, Maddon and Epstein each spoke at length about change as an organizational positive. There is surely truth to those sentiments, as there is to the rationale that the personality and skill set that made Maddon such an ideal fit for a young, unproven squad are not necessarily the best fit for managing the 2020 Cubs. Moving on was a logical decision, consistent with recent prevailing wisdom that teams should move on from even highly successful managers in the face of disappointment.
But the change likely won’t pay off. Maddon may not have been flawless, but he was remarkably successful: The Cubs ranked third in the MLB in wins during his tenure. Cubs players effusively praised Maddon and appeared genuinely saddened after his departure became official. And while he surely made mistakes, the man who was regarded as a brilliant tactician for the first decade of his career did not suddenly get dumber in the past three years. Tellingly, Epstein’s press-conference prediction that there would be a “bidding war” for Maddon appears accurate, with multiple teams reportedly interested in hiring him to replace their own recently fired managers.
Meanwhile, Epstein and the Cubs must now decide who has the strategic and interpersonal skills to step into Maddon’s enormous shoes. At best, it seems the Cubs will be making an educated guess: Of the five candidates identified publicly to date, four have never managed before, and the fifth (Joe Girardi, late of the Yankees) was let go from his previous job based on concerns about his ability to “communicate and connect with” players. Regardless of whom the Cubs select to replace Maddon, he is unlikely to succeed—at least if the only definition of success is to deliver another championship banner to Chicago. As the Cubs and their fans should know better than anyone else, winning the World Series is incredibly difficult. Sometimes it takes 108 years.