Yet in the century without a championship, the ballpark has been in first time and time again in changing the way America watches baseball.
It was the first to let fans keep foul balls. The first with permanent concession stands. The first with organ music. The first to clean the park and broadcast games as part of an effort to diversify the fan base and attract women and their kids to a game traditionally more popular among men.
"We think of all this as so obvious, but back then this was considered revolutionary," said Cubs historian Ed Hartig.
The ballpark will mark its 100th birthday this spring, and the Cubs plan a celebration in April to honor one of the nation's most classic ballparks, where runs still register on a manual scoreboard and watching a game is like taking a step back in time. As the centennial approaches, the Cubs and Chicago have found themselves stuck in a debate about how far to go in modernizing the ballpark with the same Jumbotron that towers over other fields.
"When you put a Jumbotron in the outfield I think you are messing with what makes Wrigley Wrigley," said Phillip Bess, director of graduate studies at the University of Notre Dame's architecture school and who helped lead an effort to save Fenway Park from demolition. "If the Cubs do that it means they really don't understand what it is about Wrigley that is unique (and) the kind of place people will come to even when the team is bad."
But don't be so quick to call Wrigley Field a tired, old home of a perennial loser. It may have been the last ballpark to install lights for night games, but he park's ivy-covered walls are a defining feature of what was once a sparkling, modern ballpark run by men who were trying to create a new experience for fans.
The park was built by a man named Charles Weeghman for a team in something called the Federal League, which was trying to give the more established National and American Leagues - which the Cubs and the crosstown White Sox played in - a run for their money.
After hiring the same architect who a few years earlier designed Comiskey Park for the White Sox, workers needed just two months to demolish the buildings that once housed a seminary and build a simple, single-story grandstand and the rest of the 14,000-seat Weeghman Park just in time for the start of the 1914 season. Finished two years after Boston's Fenway Park, it cost about $250,000. Two years after the park opened, the Cubs moved in.
"It was considered a great looking park, a lot nicer than the rat-infested park the Cubs were playing in on the West Side," said Stuart Shea, author of "Wrigley Field: The Long Life and Contentious Times of the Friendly Confines."
More important is that it was built with an eye to the future: It could be retrofitted and expanded, something that was considered genius, he said.
From almost the day it was built, the owners started tinkering with the place. After nine homers were hit in the first three games - an astronomical total for the time - the Chicago Federals, the original tenants, picked up the left field fence and moved it back about as much as 50 feet in some spots. In the early '20s, the Cubs expanded the seating capacity and the size of the playing field itself by slicing the grandstand into 11 pieces and moving them to create more space. The pitcher's mound today sits where the batters' box used to be.
Wrigley also was keen to understand the Cubs were losing money because women simply refused to come, or let their children come, to a filthy and unsafe ballpark.
The park, renamed Cubs Park in 1919, began to feel different than anyplace else. Shea believes the reasons start with Weegham's obsession with cleanliness, something he learned in the restaurant business. Hartig said it was William Wrigley Jr., team owner P.K. Wrigley's father, who, after a couple years of investing in the team, bought Weeghman's shares and started making changes.
"The Cubs were really the first ones to start cleaning the ballpark after every single game and (make) sure that the players always had the cleanest uniforms," Hartig said.
Wrigley also cleaned up the way the park operated.
"You could have a ticket and someone would be sitting in your seat already because the usher was bribed," Hartig said. "So coming home from the game with a bloody nose because there was a fight over a seat was not uncommon."
To fix that, Wrigley hired a professional ushering service. The Cubs also started to view the park as a "green space," kind of like an urban oasis, said Tim Wiles, former director of research at the National Baseball Hall of Fame.
The Cubs didn't invent Ladies Day. But that didn't matter; they just did it better than anyone else, letting women in the park for free for every Friday home game. At the same time, they rejected the popular notion that if they put home games on the radio fans would listen to games instead of attending them. The games simply whet the appetite of fans.
By 1927, two years after the first regular-season broadcast, the Cubs became the first National League team to draw more than a million fans.
Now, the famed ballpark is in for another makeover. The $500 million project, which includes a Jumbotron proposal, is on hold because the team wants assurances from the neighboring rooftop owners that they won't sue over obstructed views.
The Cubs have also said repeatedly they don't want to destroy what makes Wrigley one of the most popular and recognizable sporting venues in the country.
Still, the team argues Wrigley needs to be brought into the 21st century, generate more revenue and attract younger fans who expect things like Jumbotrons. Team Chairman Tom Ricketts has said he's running a baseball team, not a museum.
While some disagree, others say no change will erase what makes Wrigley Field what it is.
"The Cubs is sort of a Chicago institution that is not entirely dependent on the exact nature of Wrigley Field," said former U.S. Supreme Court Justice John Paul Stevens, who as a child watched Babe Ruth's called shot from his seat near third base. "There's sort of a spirit that goes with the Cubs."