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​Wrigley Field, the "Friendly Confines" of Chicago's lovable losers

The Chicago Cubs are in a familiar place this weekend . . . last place in their division. Still, the team's famously loyal fans dream on, including the famous one our Mo Rocca has been talking to:

As a longtime observer of Washington politics, George Will knows something about winning and losing.

The view from inside Wrigley Field's scoreboard 00:20

As a lifelong fan of the Chicago Cubs, he knows mostly about losing.

"At an age too tender to make life-shaping decisions, I made one: I became a Cub fan," he laughed.

"The Cubs have not won the World Series since 1908. Now that's two years before Mark Twain died."

But the long-suffering Cubs DO have something no other team has: Wrigley Field, the Windy City's legendary ballpark.

Does Will remember the very first time he walked in there? "I do," he told Rocca. "Sat right over there, Cubs played the Dodgers. I think it was about 1950, and I think they lost, but this may be an inference."

Did Will ever dream of playing there? "No," he laughed. "Cubs aren't very good, but I'm really bad. I played baseball briefly and badly, in Little League in Champaign, Ill. My team was the Middendorf Funeral Home Panthers. Our color was black."

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Columnist George Will with Mo Rocca at the site of many a Cubs fans' disappointments. CBS News

Will's latest book, "A Nice Little Place on the North Side," is all about his favorite pastime -- and his favorite ballpark, which this year turned 100.

George Will on throwing out the first pitch at Wrigley Field 00:29

Wrigley Field is older than the Supreme Court building, the Lincoln and Jefferson Memorials, the Golden Gate Bridge, the Empire State Building, Mt. Rushmore, and Hoover Dam.

Opened in 1914 as Weeghman Park, it was renamed in 1927 after Cubs owner and chewing gum magnate William Wrigley Jr.

The park still has its original hand-operated scoreboard (for which, Will noted, the Cubs have a lot of uses for zeroes), and then there are those legendary ivy-covered outfield walls.

"Now, you know you've got a problem when your franchise is most famous for the flora," said Will of the signature ivy. "But people come to see it. And it is emblematic of it."

But that lovely foliage hasn't always been popular with the players. In fact, Will believes that the ivy may be partly to blame for the Cubs' poisonous performance over the years.

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Justin Ruggiano of the Chicago Cubs looks for the ball in the outfield ivy hit -- a ground-rule double -- at Wrigley Field on June 5, 2014. Jonathan Daniel/Getty Images

"The Cubs decided this: The team is terrible, the ballpark's a gem. Let's get people to come to see the ballpark, not what goes on in the ballpark."

Hence Wrigley's warm and welcoming nickname: The "Friendly Confines." "They have gone out of their way to be friendly," said Will. "This was the first ballpark in which, when a foul ball went into the stands, you could keep the ball."

And Wrigley was the first ballpark to pitch itself to the fairer sex, at a time when most baseball venues skewed male, with much drinking and gambling.

"It was not a welcoming place for women," said Will. "So William Wrigley said, 'We're going to get women to come out, and make them feel safe.' So he invented Ladies Day. Ladies Day didn't just mean discounted tickets; it meant they opened the gates -- come on in free!"

Actually, Wrigley has never really struggled to fill its seats. The Cubs are the only team whose record doesn't correlate with their attendance.

"It's been a problem," said Will. "That Cub fans are so loyal - masochistic, some would say -- that their attendance does not vary directly with their won/lost record."

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Crown

"In fact, you point out that attendance at Cubs games correlates four times as much with the price of beer at the ballpark than it does with how the team is actually playing," said Rocca.

"That's right. Cub fans will put up with a lot, but not with expensive beer. So they draw the line somewhere."

But you won't catch George Will downing any of those ballpark brewskis; he watches his Cubs sober. "Exactly. And if you're not sober when you come in, you will be when you leave."

Rocca asked, "What would happen if the Cubs won the World Series?"

Will replied, "A lot of people say, 'Oh the romance will be gone, and the charm will be gone, and they won't be the lovable losers anymore.' That assumes you love losing.

"But if you don't, and I don't, then I'm prepared for the decadence of victory."


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