Over a century and a half marked primarily by disappointment, the Chicago Cubs have fired their share of managers. But never before had they done so with the warmth and gratitude that marked their farewell at the end of the 2019 season to Joe Maddon, the manager who just three years ago led the franchise to its first World Series victory in more than 100 years.
In a joint press conference announcing the decision not to extend Maddon’s expiring contract, the Cubs’ president, Theo Epstein, began his remarks with reference to “lifelong friendship” before explaining that the club and manager had mutually agreed “that this type of change is a win-win.” Maddon one-upped Epstein’s euphemisms, calling it “a great day, actually.” The apparent determination to set a new high-water mark for praise and admiration in the course of a conscious uncoupling was understandable. Beneath the smiles, both Maddon and the Cubs must have been wistful that their magical partnership had ended so soon.
“Anybody would take that five-year run including a World Series championship for the first time in 108 years,” Maddon observed at the press conference. He was right, of course: The Cubs and their fans would’ve been thrilled if they had been told, at the moment Maddon was hired, how the next five years would play out. Then again, sports fans are greedy, so once Maddon showed the Cubs what it felt like to shed their “lovable losers” label, they were loath to relapse. Indeed, Maddon may have been too effective for his own good: Whatever quibbles might fairly be raised about his tenure, his exit was hastened by the magnitude and immediacy of his success. When you do the impossible in your second year on the job, the follow-up act is a bear.
When the Cubs hired Maddon in November 2014, fans earnestly feared that they might not live to see the team win the World Series. That fatalism had been instilled not just by a century of run-of-the-mill incompetence, but also by the Curse of the Billy Goat, the black cat that walked in front of Ron Santo, the Gatorade spilled on Leon Durham’s glove, and poor Steve Bartman.
But Maddon’s hiring brought uncommon hope. During his nine years as the manager of the Tampa Bay Rays, Maddon established himself as one of baseball’s cutting-edge thinkers, becoming an early adopter of analytics and defensive shifts, and leading the perpetually under-resourced organization to the playoffs four times and the World Series once. His arrival in Chicago signaled the transition of Epstein’s rebuilding plan from collecting prospects to trying to win, and provided the credibility to sign the free-agent pitcher Jon Lester to anchor the Cubs’ starting rotation.
Maddon “embraced the target,” setting the seemingly unrealistic goal that the last-place team he inherited would make the playoffs in 2015. His optimism proved prescient, as a surprise 97-win campaign culminated in playoff victories over the Pirates and Cardinals. Maddon’s relentless positivity and nurturing approach proved ideal for talented but raw young players such as Javy Báez, whom Maddon allowed to play through their mistakes. And Maddon charmed the Chicago press with rambling stories and wit, reducing the media glare on his players. By the time Maddon arranged for actual bear cubs to cuddle with players during spring training in 2016, it was clear that he was the perfect fit to lead a young team under immense pressure as World Series favorites.
The 2016 season unfolded like a dream: The Cubs led the National League from wire to wire. In their first World Series appearance since 1945, they rallied back from a 3–1 series deficit to force Game 7 against the Indians. The Cubs’ extra-inning win, which required a 17-minute rain delay that felt like divine intervention, unleashed a multigenerational catharsis a century in waiting. Armed with a young core of talent, a big-market budget, and a legendary achievement in his pocket, Maddon surely had the best, and most secure, managerial job in the baseball world.
Except that he didn’t. Before the Cubs could even hold their championship parade, fans and the media began questioning whether Maddon almost blew the World Series with his heavy usage of the closer Aroldis Chapman (who surrendered a shocking home run in the eighth inning of Game 7, necessitating the rain delay). Chapman answered in the affirmative, Epstein acknowledged that he had been concerned in the moment, and Maddon himself eventually admitted that he had left Chapman in too long during Game 6 (when the Cubs led by seven runs). As Patrick Mooney observed in The Athletic last week, “In a strange way, the World Series win that should have made Maddon untouchable may have chipped away at his aura of invincibility.”
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.
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