For Chicago and Cleveland, an unthinkable question: What if we win?

Yes, the thought actually occurred to Alan Herman.

A few years ago, on a deep-sea fishing trip with his boat caught in violent storm, Mr. Herman began to fear for this life.

“Is this the way I’m going to die?” he worried.

Then, of course, he thought about the Chicago Cubs.

He had never seen them win the World Series. 

Beginning Tuesday with Game 1 of the World Series against the Cleveland Indians, many Cubs fans are honestly beginning to contemplate the end of that one constant in their life: For better or (mostly) worse, the Cubs were always the “loveable loser.” The team has not won the World Series since 1908 and not even appeared in one since 1945, two years before Jackie Robinson broke baseball’s color barrier.

Yes, Cleveland has not won a World Series since 1948 (baseball’s second-longest drought). But it has appeared in a World Series as recently as 1997, and this spring, basketball’s Cleveland Cavaliers broke the city’s 52-year title drought in any professional sport.

By Cub standards, their cup runneth over. 

It is a prospect that, to some Cub bleacher bums, is terrifying.

“I’m more scared of what happens if we win,” says Justin Glawe, a Cubs fan in his 30s, in a text message. “We know failure. We understand it. We know depression and sadness; some of us wallow in it. What we don’t know is success.”

The simple joys of Cub fandom

It was the same prospect facing Boston Red Sox fans in 2004, when they ended their 86-year title drought. But while the Red Sox drought was characterized by angst and frustration, the Cubs’ last 107 years have been only occasionally punctuated with enough success to generate frustration.

In that way, being a Cub fan has been less about hope than the simple pleasure of the sport – and of Wrigley Field – without the burden of expectation.

“Let’s play two,” as Cubs great Ernie Banks once said, is about the joy of the game for its sake and the knowledge that, win or lose, you can give it another try the next day.

“Life is not a challenge as much,” says Herman, who is in his 50s. The Cubs’ larger lesson is: “there’s going to be another game in your life tomorrow.”

Marty Behn, also in his 50s and a longtime season-ticket holder, remembers when there were so few fans at Wrigley that the team closed the upper deck. He’s not so worried about the existential angst over a potential Cubs win.

“It’s a great question, but … I’ve been waiting my whole life for this,” he says. “If somehow the mystique behind being a Cubs fan is lost … I don’t care.”

Indians fans won’t be outdone. Cleveland’s economic struggles, together with its futility across professional sports, had become a part of the city’s identity. “They call [the city] ‘the factory of sadness,’ ” says Matt Theel, a longtime fan.

So the Cavaliers championship and the World Series berth have buoyed spirits, perhaps disproportionately. “These things have been alleviated,” he adds.

What 'curse'?

It’s a reminder that the talk of “curses” is nothing more mysterious than making better sports decisions and changing an old mind-set.

Indians manager Terry Francona and Cubs manager Joe Maddon are cut from the same cloth in that way.

In an interview with the Cleveland Plain-Dealer, Indians’ owner Paul Dolan said Francona has given the franchise “a culture of winning, a culture of hope.” And Maddon, asked about the concept of the “loveable losers” this weekend, shrugged it off.

“You know that thing I’d always heard, about the Cubs being lovable losers, I never quite understood that,” he told ESPN, “because that’s not how I was raised. So getting here and really not paying attention to all the nonsense, the superstition that really has dragged a lot of people’s minds down – to escape that is great.”

For Herman’s part, he expects the Cubs to win. But he’s also prepared, as always, for disappointment. After all, he says, it won’t be the end of the world. “It would just mean the beat goes on.” 

Glawe just hopes that, if the Cubs do win, fans don’t lose the simple joys of being a Cubs fan.

“I just don’t want us to become jaded and forget all the 38-degree opening days when we watched for love rather than an expectation of winning.”