Presented By Mooney

Owners keep hiring young white guys with Ivy League/East Coast backgrounds to run their baseball teams, trying to sell hope to the fans and win the first press conference with the idea of the next Theo Epstein.

That implicit suggestion reduces a future Hall of Famer to a few bullet points in the media guide, underestimating Epstein’s creativity, open-minded nature, relentless approach and ruthless streak. It overlooks the unique, complex working conditions at Fenway Park and Wrigley Field. It underestimates how much the game – and his life – has changed since he became the Boston Red Sox general manager in November 2002.  

Credit Cubs chairman Tom Ricketts for not believing that myth, sensing that Epstein had grown tired of the power struggles in Boston and needed a new challenge. Ricketts made the home-run hire in October 2011 and possessed the long-range vision to invest in what’s become a very big front office. Epstein activated the five-year plan where a lot of things actually went wrong…and the franchise still just won its first World Series title since 1908.

Epstein will cast a long shadow over the GM meetings this week at the Omni Scottsdale Resort & Spa at Montelucia in Arizona, where 29 other franchises will be trying to play catch-up against the Cubs, a defending champion with arguably the industry’s best collection of young talent, a renovated Wrigley Field as an economic engine and promises of a new TV megadeal.

“He’s always looking for something, some type of competition, something to get the juices flowing,” said Darnell McDonald, who played for the Cubs and Red Sox and now works as a coordinator in the organization’s mental-skills program. “You know how they talk about Jordan? How Jordan would get mad if people weren’t guarding him hard enough and he’d get in fights in practice? Yeah, that’s him.”


Epstein absolutely hates to lose, whether it’s races up Camelback Mountain, a group outing to Topgolf, soccer at the team’s spring-training complex in Arizona or a pickup basketball tradition in the playoffs. Epstein’s crew played at the Golden State Warriors’ practice facility during a divisional-round series against the San Francisco Giants. They also took over the Staples Center’s purple-and-gold court in downtown Los Angeles one morning before a National League Championship Series game that night at Dodger Stadium.  

If that sounds like something out of “Entourage,” don’t forget that Epstein has now spent 25 seasons in Major League Baseball, or more than half his life, giving him a broad base of experience and a deep network of contacts.

Super-agent Scott Boras remembered Epstein as a young staffer with the San Diego Padres who joined Kevin Towers – the gunslinger GM at the time – for a meeting about Xavier Nady and kept asking questions. Nady’s 2000 draft class lined up with Epstein getting his degree from the University of San Diego Law School (without really going to class) and trying to build off his Yale University education and exposure to the worlds of scouting and player development.

“We talked about law school and baseball and appropriate backgrounds,” Boras recalled, launching into one of his trademark analogies. “I told him: Law school is like a rubber band on an envelope. The fact of the matter is – it’s what’s inside the envelope that matters. It helps you bundle things. But other than that, you only need it for things that are collective. The real decision-making is in the envelope.”

Really, there is no textbook for handling egomaniacs in Boston or all the wheeling and dealing in Chicago. Handcuffed by the leveraged partnership with Sam Zell’s Tribune Co., the Cubs needed Epstein’s brand name and built-in credibility from those two World Series titles in Boston to justify not operating like a big-market team.

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Epstein took the unprecedented step of not spending the entire 2014 payroll on that year’s team after losing the Masahiro Tanaka sweepstakes to the New York Yankees, essentially creating a savings account for baseball operations (and Jon Lester’s $155 million contract). When the Cubs won 97 games and two playoff rounds last year, Epstein pushed the business side to fund a $290 million spending spree on free agents.   


“As we looked to put the 2003 and ’04 clubs together, there was already an elite core in place,” Epstein told a Cubs Convention audience in January. “You had Manny Ramirez, Jason Varitek, Nomar Garciaparra, Pedro Martinez on the mound. What was needed in Boston was turning over the whole second half of the roster and buying low on players.

“With the Cubs, I think one of the things that we had to do was take an honest look at what was in the organization when we got here. And a lot of people always ask us: ‘Well, we like what you’ve done, but couldn’t you have done it quicker?’ Or: ‘Couldn’t you have tried to compete more while you were rebuilding?’

“And I honestly think looking back that this was the only choice we had to get to this point. There just wasn’t enough talent on the major-league roster. There weren’t enough resources. There wasn’t enough coming in the minor-league system.

“The biggest difference is that here we had to be really single-minded over a three-year period about just acquiring young talent to build to the point we got to in 2015.”

Boras, of course, directed all of his pointed, personal criticism (“Meet the Parents,” “All-Day Sucker”) toward a patient ownership group that wouldn’t take the bait. Boras also emphasized the idea that emerging clients like probable MVP Kris Bryant, Cy Young Award winner Jake Arrieta and All-Star shortstop Addison Russell improved markedly after joining the Cubs.

“We did a lot of business in Boston,” Boras said. “Jackie Bradley wasn’t a first-round pick. You go back into the framework of Varitek and (Derek) Lowe and Jacoby (Ellsbury) and we managed all those things. (Theo) did something smart, though – he always let the negotiations (run through) his staff. He’d have somebody else do them – and we would talk baseball.

“We always had a good rapport and good logic. The one thing that was clear to me was he really enjoyed baseball information. He liked to make collective decisions. Not just his decision. And I think that has really helped him in his career, because he’s surrounded himself with good baseball (people).

“He’s kind of had an egoless approach to being a general manager or a president where he really wanted to come out with the best decision, whether or not that was his original thought going in or not. That’s a real important quality.”

That’s one reason why the Cubs are usually heard in the echo chamber of rumors, even when Epstein didn’t have money to spend or a clear need or an obvious fit for a particular player. The Cubs are always kicking the tires or doing background work and don’t mind when others try to connect the dots, believing there can be a competitive advantage in the misinformation.


Sometimes it takes dumb luck, like when a deal with the Atlanta Braves for Randall Delgado collapses in the middle of the 2012 season. If you could have seen the look on Ryan’s Dempster’s face back then, it would have reinforced a perception that Epstein lacked interpersonal skills, viewed players only as commodities and didn’t spend enough time around the big-league team, skipping almost all of the road trips.

But then Epstein invited Dempster into the team’s offices before that July 31 deadline, working with him to approve a trade to the Texas Rangers that would yield future Cy Young Award contender Kyle Hendricks.

“He cares about the players – he really does,” said Dempster, who’s now one of Epstein’s special assistants. “Hey, man, he’s got a job to do. Sometimes it’s hard, I’m sure, to have to cut that feeling button off and make decisions that are best for the ballclub.

“At the end of the day, he understands the sabermetrics, the numbers side, and all that. But he also understands the chemistry side and guys in the locker room and what they mean. That’s rare. It’s hard to do both, and I think he does both exceptionally well.”

One scout described how draft meetings can be so exhausting, because there are times where it feels like everyone in the room has eliminated the player from consideration, only to have Epstein ask one more question and reignite the discussion. Epstein personally visited with first-round picks Albert Almora Jr. (2012), Bryant (2013) and Kyle Schwarber (2014) before the draft and each player contributed to that Game 7 World Series win over the Cleveland Indians.

“There’s a trust in Theo and his whole process,” said catching/strategy coach Mike Borzello. “You know he’s putting things together and heading in the right direction and you’re just patient about it. Over time – if you’re lucky enough to still be here – you figure it’s going to work out.”

Epstein inherited Mike Quade as manager and quickly fired him after a debriefing on the organization. Epstein hired and fired Dale Sveum and didn’t hesitate to dump another handpicked manager (Rick Renteria) as soon as Joe Maddon became a free agent after the 2014 season. Borzello is a Sveum hire who won four World Series rings with the Yankees before following his godfather, Joe Torre, to Los Angeles. Borzello helped the Cubs dig out of a 101-loss season in 2012, witnessing the entire scope of the rebuild.

“(Theo’s) the perfect guy to work far, as far as I’m concerned, because he takes everyone’s opinion,” Borzello said. “He values your opinion, whether you’re in (agreement) or not. He wants to hear why you feel the way you do. He evaluates everyone’s ideas and comes to his own decision.


“I’ve been in places before where that wasn’t really the case. You felt like a lot of people had things to offer and they really weren’t asked. And maybe you can avoid some mistakes just by using all that you have.

“Theo values that more than anywhere that I’ve ever worked.”

Epstein never trashed the place after losing the bidding war for Jose Contreras, but he had gone into those negotiations by instructing Louie Eljaua to buy up a block of rooms at the Hotel Campo Real in Nicaragua, trying to box out the Yankees and get the Red Sox closer to the Cuban pitcher. Eljaua – a trusted holdover from the Jim Hendry regime – now runs international operations for the Cubs as another one of Epstein’s special assistants.

“I believe he has a genuine appreciation for what everyone does in baseball operations,” Eljaua said, “from the scouts to the player-development people to the medical staff (to) the clubhouse guys. He will go out of his way to pat someone on the back or shoot someone a text or an email and commend them on a job well done. You may not take the time to do that as much when you’re 28 or 29 years old.

“He expects excellence – and the bar is set real high here – but I would say he’s more patient with the process than he was 15 years ago. He’s also earned the right to implement a plan that requires patience, as he’s done here. The plan still has to be executed. And he’s done an amazing job of steering the ship and making sure we all have the tools to get it done.” 

With Epstein signed to a five-year extension worth in the neighborhood of $50 million, the Cubs ending a 108-year drought really only feels like the beginning of a golden age of baseball on the North Side.