Cubs: A look inside the mind of Theo Epstein

Cubs: A look inside the mind of Theo Epstein

March 31, 2013, 8:45 pm
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He’s a great friend, but he would step on my neck, slice my throat to win. That’s just who he is.
—Theo Epstein's former boss Kevin Towers, on Epstein's competitive drive

PITTSBURGH – Theo Epstein thinks about what it will be like when the Cubs own the town again, when every pitch matters and they are the No. 1 story.

Because everyone understands all it would take to fill the bandwagon back up is pushing past .500 and creeping around the second wild card. The fans will pour out of the Addison Red Line stop and jam into the Wrigleyville bars, angling to see the TVs and making it hard to get a drink.

Forget about one day breaking the 100-something-year hex. How about a summer where people are planning their nights around Cubs games and looking for W flags instead of Class-A Kane County box scores? 

Year 2 of the president’s rebuilding project begins Monday at PNC Park, where the Cubs and Pittsburgh Pirates could be playing against a backdrop of rain and snow showers. Even after 101 losses, this is the moment to be optimistic. 

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“Now and then I see clips of what it was like during the ’03 playoffs,” Epstein said, “and that sea of people body-to-body on Waveland and Sheffield and how great a contrast it is to what it’s like now, especially on a cold April night on a Tuesday.

“That kind of pops into my head sometimes when I’m walking over to the ballpark: Hey, all this hard work (and) so many different people making sacrifices to make the organization healthier and better (is) so that we can have that sea of people out there, having a great time. (It’s) so we can play when the ivy’s starting to turn colors.”

If chairman Tom Ricketts is going to call those Tribune Co. payrolls “unsustainable” and spend like a mid-market team while Forbes assesses the franchise value at $1 billion, the Cubs are going to need someone out front.

At this time last year, the Chicago Sun-Times put Epstein on the back page walking across Lake Michigan. The former sports editor at the Yale Daily News understands the angles, though he didn’t like the feeling of being on the outside looking in, sitting there by yourself and wondering what to write about. The group dynamic pulled him into baseball.

“I’m not comfortable making it about me, because it’s truly not about me,” Epstein said. “It’s first and foremost about the players and secondly it’s about this big group of people that has come together on a common goal to work hard and sacrifice. So it should be about the organization. People should be writing about all the things that are going into making this organization healthier.

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“Obviously, we live in a world where things are boiled down to 140 characters (on Twitter). If you can focus on one person, that’s the most convenient thing to do. But it doesn’t mean I have to be comfortable with it.

“I recognize the realities of it. That’s why I pick my spots. That’s why I’m not always down there during BP. That’s why I say no to 95 percent of media requests from national writers or people that want to write things about me. And also just for my own privacy. Once you start thrusting yourself out there, I think you become a hypocrite if you then decide to draw a boundary and pull back.”

Even if Epstein is not always a natural people person, somewhat shy and quiet, he depends on that network.

It’s the new minor-league pitching coordinator (Derek Johnson) who once tutored future Tampa Bay Rays ace David Price at Vanderbilt University. It’s the scouts who will be trying to find the next Cy Young winner to grab with the No. 2 overall pick in the June draft. It’s the coaches who will be teaching and pushing top prospects Javier Baez, Jorge Soler and Albert Almora.

[POSNANSKI: Epstein's Cubs on winning track -- it just may not seem that way

Those moments will have to do for now, though talk to enough people who know Epstein and you wonder how long before he’ll need a fix. His Boston Red Sox teams won at least 95 games six times and made the playoffs during six of his nine seasons in charge.

You listened to Epstein drop F-bomb after F-bomb at Fitch Park during the front office play-in event for the camp bunting tournament. You heard about how they had to end the pickup basketball games between Epstein and his staff and the Boston media during spring training in Florida.

“Theo’s as competitive as any man you’ve ever met,” said Peter Woodfork, Major League Baseball’s senior vice president of baseball operations, a former Red Sox staffer and Harvard University infielder.

“That drive helps him, but he’s a funny guy. It probably doesn’t appear that way today, but he’s about as normal as they come. He’s not a pretentious guy. It speaks to his parents, his family. He’s a very down-to-earth person. He’s way more comfortable in jeans and a T-shirt than a suit.”

As Arizona Diamondbacks general manager Kevin Towers – his old boss with the San Diego Padres – once said: “He’s a great friend, but he would step on my neck, slice my throat to win. That’s just who he is.”

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The wins and losses are the only scorecard that matters to Epstein. Even though he gets paid like a ballplayer now, he wasn’t motivated by money and didn’t have an interest in working on Wall Street.

Towers encouraged Epstein to go to law school, to build up his credibility while negotiating with agents and strengthen a small-market front office. Epstein worked full-time while going to the University of San Diego (class of 2000), picking the classes where attendance didn’t count because he’d disappear to Arizona for spring training for six weeks at a time. 

Epstein had to find out about life inside Big Law and asked Towers if he could work from the road for two months and become a summer associate at an Orange County firm. When Epstein was offered a six-figure job, Towers doubled his salary with the Padres, which was still about half of what he would have made at the law firm.

“Well, he is the smartest guy in the room,” Jason McLeod said, “but he’s also got a very free spirit to him.”

Epstein, who passed the California bar exam, has strong political beliefs, campaigning for John Kerry after the Red Sox won the World Series in 2004 and speaking at fundraisers for Barack Obama during the 2008 and 2012 presidential campaigns. He keeps that quiet because he understands most fans don’t want to hear about the intersection of sports and politics.

Epstein wound up becoming friends with Pearl Jam after he took over as Red Sox general manager. He launched Foundation To Be Named Later with his twin brother Paul, helping organize the “Hot Stove Cool Music” charity concerts in Boston.

McLeod – now the Cubs senior vice president of scouting and player development – first met Epstein back in the mid-1990s when they were starting out their careers in San Diego.

“It just kind of boils down to (this),” McLeod said. “We were at the time just two 20-something-year-olds who loved baseball, who loved talking baseball, who loved just gulping up (information). We would read scouting reports and look at stats and just talk baseball 24/7.”

They jumped at the opportunities to scout players. McLeod still cracks up telling the story about one of their first assignments, going together to Cal State Fullerton University to see a pitcher projected to go in the top four rounds of the draft.

“I think he didn’t get out of the first inning,” McLeod recalled. “So you got two young guys like: ‘This guy (stinks), man!’ He walked like two guys and for us it was all about just his performance that night was going to dictate his future ability. We’re like: ‘This guy (stinks!) Let’s go have some beers!’

“At that time, we were like two too-cool-for-school guys that were in their early 20s working for a major-league team. … I mean, life didn’t get any better, in Southern California, hanging out in the beach-town bars.”

At the age of 39, Epstein has grown into one of the most powerful jobs in baseball. He didn’t chase the money and still got rich. He hates the attention but still became famous. He went to the organization that hasn’t won a World Series title since 1908 and…

Special assistant Tim Wilken listens to Epstein and thinks of his old boss with the Toronto Blue Jays, Hall of Fame executive Pat Gillick, the architect of three World Series winners.   

“There’s some shyness to him, but he’s confident. He is extremely thorough,” Wilken said of Epstein. “When it comes down to brass tacks and you’re talking about someone, it’s always the baseball part at the end. He’s going to crunch everything in between, but when he comes down to that final decision, it’s always baseball.

“Both of them have great memories. Pat’s nickname was ‘Se Gap Wolley,’ which meant ‘Yellow Pages’ backwards, because they said he would actually memorize phone books. Pat just had a tremendous mind (and) Theo’s got a very similar (one).”

Epstein’s mind started racing last October, during a quiet moment with his young son Jack, walking around Wrigley Field and seeing how the ivy had turned into a collage of red, yellow and orange. He flashes forward when he sees film of the old playoff teams that connected so deeply with the city.

“The Cubs aren’t associated with winning – let’s be honest,” Epstein said. “So when you do see it – whether it’s clips from ’84 or ’03 – you almost do a double-take. It gets your attention and it takes your brain to a place where it normally isn’t, which is at the top: ‘This is how great it can be and it will be.’

“You almost have to take figurative rewards or let your brain make those leaps sometimes.”