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The top 10 Cubs stories of the 2010s, #2: The hiring of Theo Epstein

The Cubs had a new baseball executive this decade. He changed everything.

Chicago Cubs Introduce Theo Epstein as President of Baseball Operations
Theo Epstein at Wrigley Field after his introduction as Cubs President of Baseball Operations, October 25, 2011
Getty Images

It’s remarkable to look back at the last eight years of Cubs baseball and wonder what they would have been like if the Boston Red Sox had won their final regular-season game in 2011.

The Red Sox seemed as if they were cruising toward a playoff spot that year. On August 31 they led the A.L. East by 1½ games, and it appeared that even if they lost that division lead to the Yankees, they’d be the then-single wild card team, as they led the Rays for that spot by nine games on that date.

Everything that could have gone wrong did. The Red Sox had a 7-20 September — even worse than the 11-16 September that put the 2019 Cubs out of the postseason — but even after that, if they had defeated the 92-loss Orioles on the season’s final day, they’d have tied Joe Maddon’s Rays for the wild-card spot.

But they didn’t. One strike away from victory, Jonathan Papelbon served up a ground-rule double to Nolan Reimold and three pitches later, Robert Andino singled in the game-winner and the Orioles won 4-3, eliminating the Red Sox.

If the Red Sox make that postseason and have a decent playoff run, is Theo Epstein as anxious to leave his hometown? In that event, would the Red Sox have been as willing to let him go? In a farewell column in the Boston Globe, Epstein wrote:

Football legend Bill Walsh used to say that coaches and executives should seek change after 10 years with the same team. The theory is that both the individual and the organization benefit from a change after so much time together. The executive gets rebirth and the energy that comes with a new challenge; the organization gets a fresh perspective, and the chance for true change that comes with new leadership. This idea resonated with me.

I’ve long believed that was a rationalization on Theo’s part, a way for him to leave Boston gracefully when they didn’t seem to have the same view of him.

If the Red Sox are in the playoffs in October 2011, Theo wouldn’t have been spotted by an eagle-eyed Cubs fan at this neighborhood Starbucks:

Mark Yellon

After originally denying it was him, Theo explained himself at his introductory news conference:

“When I’m somewhere where I don’t want to be recognized and somebody recognizes me, I have a couple standard lines I go to,” Epstein said. “I usually always say like, ‘Oh no, that’s not me, but I guess I kind of look like him. I get that a lot.’ Or I say, ‘Theo Epstein? Who’s that?’

”And I was so excited to be in Chicago and so surprised to be recognized that I dropped both lines on this guy without stopping to realize they don’t really work well in concert with each other. My mistake, and actually, I’m a little bit more of a Dunkin’ [Donuts] guy to begin with. Now that I know Dunkin’ supports the Cubs, that’s a good thing.”

I think you can see why those lines don’t work well together. After loosening up the media crowd at that news conference, Theo spoke these words that I, for one, will never forget:

“To me, baseball is better with tradition, baseball is better with history, baseball is better with fans who care, baseball is better in ballparks like this, baseball is better during the day. And baseball is, best of all, when you win,” Epstein said during a packed Wrigley Field news conference.

For someone who had spent nearly his entire life immersed in the Red Sox, it gave the feeling that he understood the situation he was coming into.

Here’s that introductory news conference from October 25, 2011:

(Aside: Wow, he looks so young. Theo was just 37 years old when he was hired.)

And then he dragged the Cubs baseball operations into the 21st Century. At the time the Ricketts family took over the ballclub, the Cubs had the second-fewest full-time employees of any MLB team (only the Marlins had fewer). With a beefed-up scouting staff and new analytics hires. the Cubs were ready to build a real organization, something they’d really never previously had.

I’ll freely admit that I read Epstein’s call for “parallel tracks” to mean he was going to try to “win now” while simultaneously doing the rebuild. With the benefit of hindsight, obviously that wasn’t possible. “Tanking,” a phrase that came into vogue in the mid-2010s, helped bring the Cubs Kris Bryant and Kyle Schwarber, and they don’t win the World Series without those guys. Shrewd scouting and trading brought the team Anthony Rizzo and Jake Arrieta, among others, culminating in the 2016 World Series championship.

Attempts to win another World Series by Theo backed him into something of a financial corner, and many of his trades and signings didn’t work out in the second half of his tenure as they did in the first. (Incidentally, despite the Cubs cruising to their most wins in 106 years in 2016, Theo’s contract extension wasn’t announced until a couple days before that year’s regular season ended.)

Does Theo truly feel “10 years is enough” in one location? Would he sign a contract extension after 2021 if offered? Do the Cubs want to start over with new management again after two more seasons?

We don’t know the answer to those questions, not yet, anyway. What we do know is that Theo Epstein’s baseball operations department brought to the Chicago Cubs something they hadn’t had in 108 years, a World Series title. No matter what happens going forward, for that we are eternally grateful.