(670 The Score) Sincerity is like obscenity – you know it when you see it.
When you hear it. When you sense it.
And Theo Epstein consistently delivered it, from his first day as Cubs president of baseball operations on Oct. 25, 2011 through a surprise news conference announcing his departure Tuesday.
Whether Epstein was addressing baseball matters in front of a microphone or engaging in casual conversation at the ballpark or bar, he connected with uncommon transparency and candor. In a baseball Theocracy, everybody and everything mattered. He could speak with an edge or eloquence, depending on the situation, and his abundance of confidence lacked pretense. He could be the smartest person in the room without feeling the need to prove it, mixing humility with humor as he maintained a self-awareness considered rare in his profession. He explained professional failures as thoroughly as he did successes, taking as much time as necessary to get his point across until his audience ran out of questions.
All of those qualities will be missed greatly with Epstein moving on, not because they made the 46-year-old Chicago’s most compelling sports executive to cover but for how that leadership style dramatically transformed the culture of the Cubs. From the front office to the dugout, Epstein infused the organization with an attitude rooted in accountability and accessibility but also relatability, something that matters when your baseball home sits in a neighborhood on the North Side.
It was on Epstein’s walk home from Wrigley Field one day years ago during the Cubs’ rebuild that he experienced something significant that he remembered as he reflected on his tenure. As Epstein recalled, he eavesdropped on a group of Cubs fans sharing their excitement over the progress of some young players on the rise.
“It felt like the line between fans and front office members and players blurred,’’ Epstein said. “It felt like we were in on a secret.’’
Epstein’s plan felt like Wrigleyville’s open secret. One of his greatest gifts as a communicator involved the ability to let people in just enough to get a glimpse without revealing too much, a strength on display again during his final hour-long media session. Epstein openly reminisced, about the time Jed Hoyer, his confidante and successor, pounded the table for reliever Pedro Strop in the famous 2013 trade with the Orioles that brought Jake Arrieta to the Cubs. About the morning after winning the 2016 World Series when Epstein woke up after passing out in his bed and realized it wasn’t a dream that had haunted him for years but the reality of feeling “free of that burden moving forward.’’ About becoming close friends with Cubs chairman Tom Ricketts, whose clandestine recruitment of Epstein after the 2011 season made everything possible. About looking forward to second-guessing Cubs manager David Ross as a season-ticket holder and enjoying a beer to get “the full Bleacher Bum experience.’’
Without the power of Epstein’s personality – that trademark sincerity – Joe Maddon never may have been persuaded to leave Tampa Bay to manage the Cubs. Without Maddon giving the Cubs credibility, who knows if Jon Lester ever would have signed a free-agent contract with the Cubs before the 2015 season? And without Lester …? The Ricketts family purchased the Cubs in 2009, but legitimacy arrived when Epstein did two years later.
“Early on, he promised us sustained success,’’ Ricketts said Tuesday. “He delivered sustained success.’’
To deliver on his promise, Epstein modernized an operation stuck in the past, turning an old-school mentality into a private-school approach, sparing no expense to give the Cubs state-of-the-art facilities and technology. He developed a plan at the major and minor league levels and followed it, fearlessly bottoming out because he recognized that was the shrewdest way to climb to the top. He made more smart moves than dumb ones and admitted the biggest regret he leaves with stems from the Cubs’ lack of postseason success since winning it all in 2016.
Perhaps the ultimate compliment for Epstein comes in acknowledging he raised expectations so high that it feels as if he leaves having not met them. As absurd as it sounds, Epstein set such a lofty standard that winning the most elusive championship in sports wasn’t enough. He conditioned Cubs fans to expect championships, plural. Many baseball observers figured at least another World Series title would follow their epic championship but, alas, baseball happened. The Cubs offense broke, irreparably. The core of players whom Epstein expected to carry the team dropped off significantly. Gradually, the window began to close.
Nothing ever can replace the sweet satisfaction the Cubs created for their fans on that magical night in Cleveland after Kris Bryant cleanly fielded the grounder and fired the ball to Anthony Rizzo for the final out to end baseball’s longest wait. Nor can anybody deny feeling a tinge of disappointment that history didn’t repeat itself under Epstein. Yes, the Cubs sustained success as he promised on Day 1. But they didn’t build a dynasty as the 2016 Cubs implied. One day that still might nag Epstein, perhaps when his career gets a full accounting upon his inevitable entry into the Baseball Hall of Fame in Cooperstown.
And so the curtain closes on Cubbie Camelot, one brief shining moment in franchise history that lasted nine years but seemed shorter. Nobody calls the Cubs lovable losers anymore. Nobody mocks the idea of “The Cubs Way’’ that Epstein brought to town. Nobody can argue that Epstein became the new standard by which sports executives in our city are measured.
What’s his encore? What's next? Baseball needs Epstein more than Epstein needs baseball. For the first time since he was a teenager, Epstein looked forward to a summer without having to go to the ballpark unless he wanted.
He invoked the example of late Hall of Fame football coach Bill Walsh, who believed in changing jobs every decade. Epstein walked away from a $10-million salary in 2021, in the midst of a pandemic, because the Cubs face another rebuild with massive changes ahead requiring, as Epstein put it, “decisions best made by somebody who’s going to be here a long time, not just a year.’’ He resisted the idea that he felt “burnout’’ and carefully avoided ruling out anything, knowing himself well enough to realize how much he can't resist a great challenge. He referenced a future in baseball that may involve running another team or perhaps owning part of one.
There will be some who push Epstein to one day replace MLB commissioner Rob Manfred. There might be others – Bears fans? — who would love to see Epstein try his hand running an NFL team. The political arena? The entertainment industry? There will be no shortage of options for a man of many talents still four years shy of his 50th birthday.
Someone asked the former Yale sports editor if he would write a book.
“That’s for old people,’’ Epstein quipped. “And great former presidents.’’
What a unique chapter Epstein just closed.