Front-Row Seat

The Cubs are poised to return to the postseason, thanks in part to Theo Epstein's grand vision

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“The game is best understood at 10,000 feet. But it is best enjoyed from the front row.”

— Chicago Cubs President Theo Epstein

CHICAGO — Theo Epstein said this to me a few years ago, just after he got the Chicago Cubs job, and he has repeated the quote to me many times since. It is probably the closest thing Epstein has to an all-encompassing baseball philosophy. Sure, there are other credos for him such as, “Control the strike zone from both sides of the ball” and “Nobody holds a press conference at the END of a big contract,” and “You want a lineup that is relentless one through nine,” and “The best way to cover your bases is to make a series of small bets.”

But these are smaller philosophies – sub-philosophies, you might call them.

The big one, though, remains this: The game is best understood at 10,000 feet. This was the driving point when I sat with Theo Epstein in his office during spring training in 2012, not long after he became the latest brave soul to take on the Thirteenth Labour of Hercules:

1. Bring back the skin of the Nemean Lion.

7. Wrestle the Cretan Bull.

11. Steal the golden apples of the Hesperides, guarded by a 100-headed dragon.

13. Lead the Chicago Cubs to the World Series.

As just about everyone noted at the time, there was something poetic about Epstein taking on the Cubs’ test. He had already been a pivotal figure in a baseball miracle; his Boston Red Sox (the team he grew up cheering AND the team he ran as general manager) won the World Series after 86 years of wandering in the desert.

But this was quantifiably different. The Red Sox had for decades been good but luckless. Between 1967 and 2003, they had played in October TEN times, and that included three World Series which they lost in seven games. In those 37 seasons, they finished with a winning record 29 times – the Red Sox were not fundamentally broken. They were not cursed either. They were simply unfortunate in the biggest moments. And then, suddenly, they were fortunate.

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The Cubs? Whole different thing. The Cubs have not even BEEN to a World Series since the year World War II ended. Since 1946, the team has lost 700 more games than it has won. Epstein will readily tell you he took over a Red Sox team that already had a Hall of Fame cast – Pedro, Manny, Varitek and so on. When he took over the Cubs, well, they had just lost 91 games. It was the ninth time since 1980 that they had lost 90-plus games.

And Epstein’s first year? They lost 100 games, something even the Cubs had managed to avoid since 1966. And here was the crazy part: Epstein KNEW they would. Well, maybe he didn’t know the exact won-loss record, but he knew the Cubs would be terrible that first year, and he knew they would be terrible the second year, and he suspected they would probably be terrible the third year and maybe the fourth year also.

This was the plan for Epstein, who is the team’s president, general manager Jed Hoyer and all the coaches and scouts and analysts working for the Cubs: Dispassionately build a new kind of Cubs team. They reviewed their assets. They had a young shortstop, Starlin Castro, and a couple of possibilities in the minor leagues and … well, the team had hit bottom. There were advantages. With losing comes high draft picks: Take advantage. With losing comes a willingness to make changes: Take advantage.

And the most important part was: Do not get distracted. Get up to 10,000 feet and, no matter how stormy the weather got, do not lose altitude. Make trades that may hurt in the short term but help in the long term. Avoid the pitfalls of the quick fix. Keep the bets small until the team is ready to compete. Revamp the minor-league system. Build a wide-ranging philosophy on everything from what to look for in player attitudes down to how to round first base on a single (“The Cubs Way!”) and make sure that everyone, from the players to the coaches to the video guys to the ticket takers to the vendors, embraces that philosophy.

Now, here we are, four years later, and the Cubs are in position to make the playoffs for the first time in years. They are being led by a bunch of kids. They are exciting and likable and already really good with blue skies ahead – truth is they are winning more quickly than anyone, including Theo himself, thought possible. They are providing something foreign to the baseball fans on the North side of Chicago: Hope.

So all that’s great. But what of the second part of the Theo Theology? What about: “But it is best enjoyed from the front row?”

“Yeah,” Epstein says, and he half-smiles. “I’m doing the best I can to enjoy.”

This, for Epstein, may be the greater challenge. The enjoyment part just does not come easily to Theo Epstein. He wonders if this is the Boston in him, wonders if this is the inborn New England certainty that doom, inevitably, awaits. “Into each life some rain must fall,” wrote that cheery New Englander Henry Wadsworth Longfellow. “Some days must be dark and dreary.”

“This September is going to be enormously challenging,” Epstein says. “September is extremely hard on everyone. They’re so young and inexperienced and we’re being chased by a three-time World Champion and it’s just so tough because there will be times with a young team when you wonder how they ever even won two games in a row and …”

He can’t help it. The Cubs began Thursday 7 1/2 games up on the Giants with 17 games to play – their magic number to clinch a Wild Card berth Is down to 10 – but if you bring up such things Epstein will remind you that his 2011 Red Sox seemed like a playoff lock too, and that ended horribly. Epstein needs to worry. He needs a crisis to manage and a dragon to slay. It is in his nature.

This, I’ve long suspected, was the reason he took the Cubs job in the first place. He’s hinted around this in conversations but I’ve never quite gotten him to just admit it: I think things were too easy in Boston. Oh, sure, they weren’t easy at all in 2011, when the Red Sox made a bunch of splashy signings and the team imploded in September and there were all sorts of silly controversies like the one about some high-profile pitchers supposedly squatting in the clubhouse during games, eating chicken, drinking beer, playing video games.

But, let’s be honest: These were first-world baseball problems. Even the disastrous 2011 Red Sox won 90 games. They averaged 93 wins in Epstein’s years as Boston’s general manager, and they never had a losing record, and they won two World Series, and came awfully close two other times. He enjoyed building the minor-league system and did a good job at it. But, realistically, the Red Sox had the money to paper over mistakes and the history and fan base to bring in just about anyone they wanted.

Sure, there were challenges in Boston, extreme challenges, as we have seen in Boston in the years since he left (though even in those spotty years the Red Sox won another World Series). And he obviously loved the Red Sox all his life. But for someone like Theo Epstein, who craves the “dare to be great” challenge, I think Boston was frustrating.

Chicago offered that challenge. Here was a moribund organization with an ill-fated history and a flagpole from which they often hung an “L” so that the passenger in the passing El Train would know that the Cubs lost again. The Cubs had a 30-something outfield making about $40 million, an overpriced one-time ace who had been suspended for the last month of the season and a blah minor-league system without a Baseball America Top 30 prospect. It was pretty dismal.

Epstein, I suspect, did not take the job in SPITE of all those challenges. He took the job BECAUSE of all those challenges.

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He and Hoyer cleared house. Remember that scene in the movie “Hoosiers,” where Norman Dale has his team practice for a long time without basketballs. That was the Cubs in 2012. The entire thing was about changing the mindset and making some small adjustments (like moving Jeff Samaradzija to the rotation) and writing “The Cubs Way” manual and losing. Lots and lots of losing. People in Chicago have certainly seen their share of losing through the years, but that 2012 version of the Cubs was particularly grim, with the team losing 43 of its last 61 games, scoring one or fewer runs 16 times in the process. Like in Hoosiers, there were plenty of grumbles that the guy might not know what he’s doing.

“In this era, we decided it might be harder to find young hitters that can control the zone and hit for power,” Epstein says. “They’re hard to find. Teams won’t give them up when they do find them. It wasn’t any bit of genius, we just thought that whether it’s through the draft, through trades, we were going all in on hitters. It’s like being at the roulette table. You can’t cover every number. You have to pick your spots. We started with hitting.”

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Epstein likes the roulette analogy. The Cubs didn’t do anything overly bold in those early years. Like he says: They just made a series of small bets. Epstein and the Cubs traded for a favorite prospect of his, Anthony Rizzo. They drafted Kris Bryant and Kyle Schwarber with their first-round picks. Samardzija took well to starting pitching, so they traded him at top value to Oakland for gifted young shortstop Addison Russell. They made a couple of small pitching bets too – trading for fading pitching prospect Jake Arrieta and drafting a hard-throwing but raw Hector Rondon in the Rule V draft.

None of these moves, with the possible exception of the Samardzija deal, made the front page. The Cubs got a little bit better in 2013, and they played surprisingly well in the last couple of months of 2014. And that’s when Epstein decided it was time.

“I think we flipped that switch because of a number of factors,” Epstein says. “Last year, the most important thing was to play well enough to put us in a position to get more aggressive. We did that. Rizzo had a breakthrough season for us. Arrieta had a breakthrough season. We drafted Schwarber and he took a step forward in his timetable. Bryant exploded.  And then, Joe Maddon fell into our laps.”

Everyone around the Cubs – management, players, fans, everybody – will say that it was Maddon who took the team from the 10,000 feet phase to the front-row phase. Maddon has long been one of baseball’s best managers, but his transition from Tampa Bay to Chicago was a little bit messy. Maddon opted out of his contract with the Rays and became a free agent. The Cubs fired manager Rick Renteria barely a year after hiring him, a move that gutted Epstein and briefly created a storm.

“We saw it as a unique opportunity and faced a clear dilemma: be loyal to Rick or be loyal to the organization,” Epstein wrote in a statement at the time. “In this business of trying to win a world championship for the first time in 107 years, the organization has a priority over any one individual. We decided to pursue Joe.”

With Maddon in place, Epstein and the Cubs stopped making little bets and started making big ones. They signed pitcher Jon Lester for big money. They brought back pitcher Jason Hammel for pretty big money. They traded for a veteran leadoff hitter, Dexter Fowler, and they began calling up (or recalling) the kids, all of them – Bryant, Schwarber, Russell, Jorge Soler, Javier Baez, Matt Szczur, on and on.

At the start, the Cubs looked raw but interesting. They hovered around .500 until June, and then began to take off. Pitching got them going. Arrieta had improbably developed into one of the game’s best pitchers. Rondon anchored a better-than-expected bullpen. In August, the young lineup turned it on. The Cubs hits 44 home runs, averaged five runs a game, wore pitchers out with (using Epstein’s favorite word) their relentless approach.

“Not that it’s a perfect measuring stick by any means,” Epstein says, “but if you look at our pitches per plate appearance, we were 30th and we increased it a little bit each year. Now we lead the league in pitches per plate appearances. Our walks and our on-base percentage have followed suit – it’s the same in the minor leagues. We have a ton of guys who know how to grind out at-bats.

“That’s really what makes us tick. We’re very proud of the organization. This was the plan, but it’s a difficult transition to effectuate. We strike out a lot but we walk a lot, our home runs are up … we haven’t had too many starting pitchers get deep into the games against us unless they have a Cy Young on their resume. And you can see in the third or fourth game of series that bullpens are worn out against us.”

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Epstein smiles: “We view this as the beginning,” he says. “But we’d like to make it to October this year and we’d like to do some damage in October.  You can’t take anything for granted. You never know how many times you’re going to get there.”

Which leads back to the question of how much Epstein is enjoying the ride. He says that he is enjoying it, but he says it without his voice raising even a little. He tells a cool little story. Every day, he walks back to home after games – he lives fairly close to the park.

“There’s a difference from three or four years ago,” he says. “First of all, I did not have that much company walking back with me then. But it felt like part of the ‘Walking Dead’ walking back. There was no energy coming from the game, from the park. It was all about, ‘What are we doing next?’ And that was painful. That was tough, seeing all those long faces. People did recognize me and they gave lots of advice or they questioned what we were doing.

“Now, walking back, you feel like you’re part of a party on the sidewalk. People are floating home from the ballpark, really happy. You walk back and you’re walking with a Bryant jersey or Rizzo jersey or Schwarber jersey. It’s a collective experience.”

And this seems to be as far as as his New England nature will let him go. In Chicago, the party is in full force – and Chicago knows how to party. Epstein seems content to enjoy it from a remove (a collective experience). Only then, I ask him about his 7-year-old son Jack. And then, well, his whole face brightens. And he digs in.

“He’s had his first real little league season,” Epstein says. “It is his first time following a team, his first time reading the rulebook cover to cover. He has a deep understanding of the game. And he’s in.”

Now Epstein’s voice gets louder and more excited.

“He loves this team. He came out on the road with us to four games, and it seemed like we won every one of them on a walk-off hit. We hit five home runs. We won four games in a row. And now he thinks that’s what baseball is. Every morning he asks me, ‘Dad, did we win or lose?’ And if we lost, he’s like, ‘What? We lost again? What is happening?’ He thinks we should always win.

“It’s been like that all year. Not just for him. It’s like that for the team, if you were to take a snapshot of the season, it would be another young player comes up. He hits a game-winning home run. Oh, hey, we won. Thirty-five thousand people are happy. We get to go celebrate and play softball and have a beer and go out. And oh yeah, we get to to do it again tomorrow with another young player coming up. It’s a surreal baseball paradise.”

And with this, Epstein looks out on the field happily as batting practice goes on. Sure, he has to go back to 10,000 feet, has to go back and see what trouble awaits. But every now and again he he realizes, man, it’s true: It really is a great view from the front row.