Massarotti: Chicago Cubs And The Culture Of Winning

By Tony Massarotti

At the risk of dating myself, does anyone remember that famous scene in When Harry Met Sally, when Meg Ryan feigns an orgasm in the middle of a diner? An older woman seated nearby takes in Ryan’s act, then eagerly tells the waitress, “I’ll have what she’s having.”

This is how I feel about Theo Epstein.

I’ll have what he’s having.

The Cubs are back in the National League Championship Series, folks. For the first time in their history they have reached the NLCS in consecutive years. And they did so last night with a wildly improbable 6-5 win over the San Francisco Giants, scoring four times in the ninth inning to erase a 5-2 deficit. That leaves Madison Bumgarner in the bullpen all winter, destroying any chance of further heroics from him this October.

Here’s the ultimate conclusion: the old Cubs would have lost this game, landed in Game 5, resurrected decades of torturous history after a historic season in which they were indisputably the best team in baseball. But the new Cubs? They win this game now, and they do so in dramatic fashion to continue a seemingly methodical march toward immortality.

At least for now.

In the middle of it all stands Epstein, who looks more and more like baseball’s chosen one following a night on which the Cubs were positively stifled by Matt Moore. Twelve years ago, Epstein helped the Red Sox over the hump to their first world title in 86 years, overcoming a 3-0 American League Championship Series deficit to the New York Yankees in the process. Three seasons after that, the Sox won another world title after overcoming a 3-1 ALCS deficit to the Cleveland Indians, showing the kind of determination and resiliency that seems indisputably evident in these Cubs.

After that win over Cleveland, Epstein stood near the home on-deck circle at fabled Fenway Park, acknowledging that a new generation of Boston players — from Dustin Pedroia to Jon Lester — would never have to deal with the burden of organizational failure because, well, the Red Sox weren’t losers anymore.

“That’s a great thing to have associated with your organization,” Epstein said. “It establishes a real culture of winning and overcoming obstacles throughout the organization. You can’t teach that.”

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Are the Cubs headed there now? There are obviously still hurdles to clear. After Aroldis Chapman blew a save Monday night, the Cubs showed up on Tuesday for Game 4 and fell behind early. The Cubs tied the score at 1 before the Giants went ahead by scores of 3-1 and 5-2, and you could see fans squirming on the North Side (whine country?) all the way out in wine country.

And then this happened: a single by Kris Bryant, a walk by Anthony Rizzo and a double by Ben Zobrist. It was 5-3 with runners at second and third. Willson Contreras delivered a two-run single to tie the score before a Jason Heyward bunt and throwing error by Giants shortstop Brandon Crawford, then a go-ahead single by Javier Baez.

Twenty-two pitches, six batters, five runs. And just like that the Cubs were in the NLCS.

“Nobody really cares in [the Chicago clubhouse] about a curse or a goat or anything else,” former Red Sox pitcher and current Cubs ace Lester told reporters after last night’s win. “If we make a mistake, we’re not going to blame it on a curse or anything else like that. We’re going to blame it on ourselves and be accountable for it and move on to the next play or the next moment. … We’ve got too many young guys in there that don’t even know what that stuff is, you know what I mean? So, it’s almost better to play naive and just go out and worry about us, worry about the Cubs and not anything else in the past or, like I said, any animals.”

Lester would know, of course. He was the very first draft pick of the new Red Sox in 2002. He was reared in a winning culture that knew nothing else.

That’s the same culture Epstein and the Chicago Cubs might soon possess.

Tony Massarotti is an avid Boston sports fan and has covered sports in Boston for more than 15 years for both the Boston Herald and Boston Globe. He now serves as a co-host on afternoon drive on 98.5 The Sports Hub in Boston. He was a two-time Massachusetts Sportswriter of the Year as voted by his peers and has written four books, including “Big Papi,” the New York Times-bestselling memoirs of David Ortiz. You can follow Tony @tonymassarotti.

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