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Dan Shaughnessy

Cubs looking like the Red Sox’ baseball cousins

Team president Theo Epstein (right) and manager Joe Maddon were the key leaders for a Cubs team that won 97 games this season.Jeff Haynes/Associated Press/File 2015

Theo Epstein isn’t complaining. His Chicago Cubs just finished their regular season with 97 wins, which hasn’t been topped by any Cubs team since 1945, and the Cubs’ whole season could be over Wednesday night . . . but Theo knows that’s how the playoffs work. He was a little kid in Brookline when the 99-win Red Sox were taken out of the playoffs by a swing of Bucky Dent’s bat back in 1978.

Doesn’t matter. That’s October baseball. And there’s no crying.

Nothing in baseball beats a one-game playoff. That’s what we saw Tuesday night when the Astros beat the Yankees, 3-0, and that’s what we get Wednesday night in Pittsburgh when the Cubs and Pirates — two of the three best teams in baseball — play a single game for the right to move into the Division Round.

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“I accept it,’’ says the former Boy Wonder general manager of the Red Sox who is finishing his fourth year as baseball boss of the Cubs. “I understand why baseball came up with it. You can’t take too long with this round. It’s not fair to let the division winners stand around and get cold, like the Rockies did in 2007.

“There’s no denying that starting the postseason with two Game 7s, essentially, is great for TV. It’s really hard to have a gripe if you don’t win your division. Baseball’s not supposed to be completely fair.’’

Much as we love Pittsburgh, its ballpark, and its storied baseball franchise (last World Series win, 1979), the Cubs go into the 2015 postseason baseball tournament as America’s Team. And it’s not even close.

Remember the days when everybody was rooting for the Red Sox? Curse of the Bambino? Near-misses year after year? Legendary old ballpark? Young Theo Epstein running the baseball operation?

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That’s what’s going on in Chicago this year.

The Cubs have not won the World Series since Teddy Roosevelt was finishing his first full term as president in October of 1908. The Cubs have not won a postseason game since a fan named Steve Bartman decided it would be a swell idea to reach over the rail and try to catch a foul ball that Cubs outfielder Moises Alou was waiting to snag (when the doomed Cubs were five outs from getting to the World Series in 2003).

The Cubs play in an ancient ballpark with ivy-covered outfield walls. And their long-suffering fans believe that this is finally the year. The Cubs are the Red Sox’ baseball cousins.

“There are a lot of similarities to where we are now and where we were with the Red Sox, pre-2004,’’ says Epstein, who signed a six-year deal with the Cubs after quitting the Red Sox in the wake of the epic 2011 collapse. “In Chicago, we have a passionate, loyal, dedicated, emotional fan base that deserves the ultimate prize. I think there’s just a slight difference in sensibilities with the fan base.

“I only get away with saying this because I consider myself a Bostonian, but being a Red Sox fan growing up, there’s a little bit more of an edge to the Boston fan base.

“It’s a little more cynical, expecting the other shoe to drop, even in good times. You sort of sense that tension at Fenway at times.

“Here, it’s just the opposite. Even in the face of a losing century, there’s a sense of optimism when you still enjoy your day at the ballpark with sunshine, sitting in the bleachers, having a few beers. There’s a personal, familial connection to the team that really resonates.

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“Because of that, it’s the best feeling in the world to help those fans enjoy meaningful games in October. It’s the worst feeling in the world to disappoint them.’’

Losing Wednesday would be wildly disappointing because the Cubs have a starting pitcher who has been close to unbeatable this season. Jake Arrieta finished 22-6 with a 1.77 ERA, and after the All-Star break, he compiled an ERA of 0.75. It’s almost too good to be true, which would certainly inspire fear in the bad old days of Red Sox Nation.

“He’s so ready for this moment,’’ says Epstein. “He’s walking around a little bit like John Wayne now, with a lot of confidence, and his teammates really pick up on that. It’s been good for our club.’’

Epstein’s manager is the inimitable Joe Maddon, an irreverent, somewhat kooky philosopher, famous for reinventing baseball every other week. Maddon, 61, was almost hired by the Red Sox but Epstein instead selected Terry Francona in 2004. Rejected by the Sox, Maddon went on to challenge Boston from the Tampa Bay dugout for nine seasons.

“When you’re on the other side, you know that his teams are always the aggressor,’’ says Epstein. “They always played loose. They always dictated the game. They didn’t back down from anybody, and players seemed to love him.

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“But you never know until you’re in the same clubhouse with him every day whether it’s sort of a manufactured act or whether it’s the real deal. Now, I know. The players are, like, 35-40 years younger than him and they really like him.’’

How does Epstein feel about Jon Lester, who went 11-12 with a 3.34 ERA after signing a six-year, $155 million deal with the Cubs last December?

“He pitched great — clearly one of the top 10-15 pitchers in the National League,” says Epstein. “Two hundred innings, 200 strikeouts. He pitched in big games for us, pitched in some bad luck when he’d go seven strong and take a loss.

“He brought a winning attitude to the clubhouse right away. We feel great about him. He had base runners going crazy on him in April and it would have been really easy to fold his tent and he didn’t. The way he rallied in the face of that adversity showed a lot to his teammates. I’d definitely re-sign him again.’’

What is Epstein’s assessment of how things went down with his former team this year?

“It looks like Ben Cherington did a hell of a job,’’ he says. “Honestly, I don’t want to get too involved in the politics of it at all, but I’d say that I still follow the players we acquired while I was there and that Ben helped develop and break into the big leagues, and I just think that they’re in good hands and that Ben’s leadership will be seen through a very kind lens when it’s all said and done.

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“When Bogaerts, Betts, Bradley, Swihart, Owens, and all those guys reach their ceilings and hopefully win a World Series in Boston — you can’t talk about those guys without talking about Ben’s role in helping acquire them when I was there and helping develop them when I left.

“The timing [of Cherington’s firing] was horrible and I feel terrible for him. He’s one of the most significant figures in Red Sox history in the last 15 years, playing an incredibly meaningful role.”

Epstein had less to say about the ousting of his former mentor/nemesis Larry Lucchino (“Obviously he had an enormous impact. Larry did a lot of great things when he was there.”), but it doesn’t matter anymore. It’s ancient history.

Epstein’s new mission is winning a World Series for the century-starved Cubs, and the only game that matters now is Wednesday night in Pittsburgh.


Dan Shaughnessy is a Globe columnist. He can be reached at dshaughnessy@globe.com. Follow him on Twitter at @Dan_Shaughnessy.