Chicago Cubs Fans — 108 Years of Loyalty Finally Rewarded

The North Side Faithful: A Century of Hope, Heartbreak, and Redemption

The Chicago Cubs are one of the oldest franchises in professional sports, founding members of the National League in 1876. They won back-to-back World Series titles in 1907 and 1908, establishing an early dynasty that their fans assumed would continue for decades. No one could have imagined that the 1908 championship would be the last for over a century — that generations of Cubs fans would live and die without ever seeing their team win it all.

The Cubs of the early twentieth century were a powerhouse, winning multiple pennants and playing in some of the most memorable games in baseball history. But as the decades passed and the championships didn't come, something remarkable happened: the fan base didn't shrink. It grew. Cubs fandom became defined not by winning but by loyalty itself — by the act of showing up, season after season, generation after generation, in defiance of disappointment.

Wrigley Field: The Heart of Cubs Fandom

Wrigley Field, which the Cubs have called home since 1916, is the physical embodiment of the fan experience. Built in 1914, it is the second-oldest ballpark in Major League Baseball (after Fenway Park in Boston) and is considered a national historic landmark. Its ivy-covered outfield walls, hand-operated scoreboard, and intimate neighborhood setting make it unlike any other stadium in professional sports.

For Cubs fans, Wrigley is more than a venue — it is a family heirloom. Grandfathers take grandchildren to the same seats where their own grandfathers took them. The smells of hot dogs and beer, the sight of the ivy turning from green to brown as autumn approaches, the sound of the El train rumbling past — these sensory experiences are shared across generations, creating a continuity of fan experience that stretches back over a century.

Wrigley Field did not have lights until 1988, meaning that for most of its history, all Cubs home games were played during the day. This created the tradition of the "day game at Wrigley," which became central to the Cubs' cultural identity. Office workers called in sick, college students skipped class, and retirees made afternoon baseball a daily ritual. The daytime schedule gave Wrigley a casual, convivial atmosphere that distinguished it from every other ballpark in America.

The Curses and the Heartbreak

Cubs fandom is inseparable from its mythology of curses and heartbreak. The most famous is the Curse of the Billy Goat. In 1945, during the World Series against the Detroit Tigers, Billy Sianis was asked to leave Wrigley Field because his pet goat, Murphy, was bothering nearby fans. Sianis allegedly cursed the team, declaring they would never win the World Series again. The Cubs lost the series, and the curse entered baseball folklore.

For decades, the curse seemed to hold. The Cubs did not return to the World Series for 71 years. Along the way, there were agonizing near-misses that deepened the mythology. In 1969, the Cubs held a commanding lead in the NL East before collapsing in September, losing to the "Miracle Mets." In 1984, they were five outs from the World Series before a ground ball went through Leon Durham's legs. And in 2003, the Steve Bartman incident — when a fan interfered with a foul ball during the NLCS against the Florida Marlins — became one of the most infamous moments in baseball history, leading to a Cubs collapse and another season of heartbreak.

Each of these moments could have broken a fan base. Instead, they strengthened it. Cubs fans developed a darkly humorous fatalism — "Wait till next year" became the unofficial motto — while maintaining a stubborn, irrational hope that the next season would finally be the one. This combination of suffering and optimism became the defining characteristic of Cubs fandom.

2016: The Greatest Championship in Sports History

When the Cubs won the 2016 World Series, it was not merely a baseball championship — it was the resolution of the longest narrative arc in sports history. The journey to the title was itself the stuff of legend. Manager Joe Maddon's team, built by general manager Theo Epstein (who had previously broken the Red Sox's 86-year curse), featured a core of young stars including Kris Bryant, Anthony Rizzo, Javier Báez, and Addison Russell.

The World Series against the Cleveland Indians was a seven-game epic. The Cubs fell behind three games to one — and many fans, conditioned by decades of heartbreak, began to fear the worst. But this time was different. The Cubs won Game 5, Game 6, and then Game 7 in a 10-inning masterpiece that featured a rain delay, a game-tying home run by the Indians, and a go-ahead RBI double by Ben Zobrist in the 10th inning.

When Mike Montgomery recorded the final out, the reaction was unlike anything in sports history. At Wrigley Field, where fans had gathered by the thousands to watch on screens, the roar was deafening. Across Chicago, strangers embraced in the streets. Grown men and women wept openly. Fans drove to cemeteries to visit the graves of parents and grandparents who had died without ever seeing the Cubs win. The victory parade drew an estimated 5 million people to downtown Chicago — one of the largest peaceful gatherings in human history.

The Cubs Fan Identity After 2016

The 2016 championship changed Cubs fandom in profound ways. For a century, being a Cubs fan was defined by waiting. After 2016, the identity shifted — Cubs fans could finally call themselves champions, but they also carried the weight of all those years of patience. The championship did not diminish the fan base's passion; if anything, it intensified it, because fans now understood how precious and fleeting victory could be.

Today, Wrigley Field continues to draw millions of fans per season. The Wrigleyville neighborhood has been transformed by development, but the core traditions — the ivy, the scoreboard, the seventh-inning stretch, the rooftops — endure. The Cubs remain one of the most popular and best-attended franchises in Major League Baseball, and their fan base stretches far beyond Chicago, reaching across the Midwest and into every corner of the country.

Icons of Cubs Fandom

The celebrities, characters, and everyday heroes who define what it means to be a Cubs fan.

Bill Murray

Bill Murray is the most famous Cubs fan in the world and arguably the most passionate celebrity sports fan in American culture. Murray grew up on the North Side of Chicago, attended Cubs games as a child, and has remained a devoted fan throughout his decades-long career in Hollywood. He was present at Wrigley Field and in Cleveland for the 2016 World Series, and the images of Murray crying tears of joy after the final out became one of the most iconic photographs in sports history. Murray's love for the Cubs is genuine, deep, and spans his entire life — he is the embodiment of the long-suffering fan finally rewarded.

Eddie Vedder

Pearl Jam frontman Eddie Vedder is a lifelong Cubs fan who grew up in suburban Chicago. Vedder wrote and recorded "All the Way," a song about being a Cubs fan that became an anthem for the 2016 championship run. His emotional performance of "Take Me Out to the Ball Game" during the seventh-inning stretch at Wrigley Field is a fan-favorite tradition. Vedder represents the artistic, emotional side of Cubs fandom — the understanding that supporting this team is not just a hobby but a deeply felt part of one's identity.

Ronnie "Woo Woo" Wickers

No discussion of Cubs superfans is complete without Ronnie "Woo Woo" Wickers, who has been attending Cubs games at Wrigley Field since the 1960s. Known for his distinctive "Woo! Woo! Cubs! Woo!" cheer, his full Cubs uniform, and his presence at virtually every home game for over five decades, Ronnie Woo Woo is the living embodiment of Cubs fan culture. He is a Wrigley Field institution — as much a part of the game-day experience as the ivy on the walls or the "W" flag on the scoreboard.

The Bleacher Bums

The original Bleacher Bums of the late 1960s and 1970s were a rowdy, passionate group of fans who gathered in the cheap outfield bleacher seats to drink, cheer, and create an atmosphere that became legendary in baseball. The group included future famous Chicagoans and inspired a hit play. While the original Bleacher Bums are long gone, their spirit lives on in the bleacher sections of modern Wrigley, where the most vocal and enthusiastic Cubs fans continue to gather.

The Generational Fans

The true icons of Cubs fandom are the anonymous families who have passed their loyalty down through four, five, and even six generations. These are the great-grandchildren of fans who watched the 1908 World Series, who grew up hearing stories of a championship they could barely imagine, and who raised their own children to believe that someday — maybe — it would happen again. When it finally did in 2016, many of these families experienced it together, closing a circle of hope that had been open for over a century.

Traditions That Define Cubs Fan Culture

The Seventh-Inning Stretch

While the seventh-inning stretch is observed at every baseball game, the Cubs have made it uniquely their own. The tradition of a celebrity guest leading the crowd in singing "Take Me Out to the Ball Game" began under broadcaster Harry Caray, who would lean out of the broadcast booth with a microphone and lead 40,000 fans in an off-key, joyful rendition of the classic. After Caray's death in 1998, the Cubs continued the tradition with guest conductors, and being invited to lead the stretch at Wrigley Field became one of the most coveted honors in Chicago. Every guest performance is a tribute to Caray and a celebration of the communal spirit that defines Wrigley.

The "W" Flag

After every Cubs victory, a white flag with a blue "W" is flown from the center field scoreboard at Wrigley Field. The tradition dates back to the days before electronic scoreboards, when the flags told fans approaching the stadium or riding the El train whether the Cubs had won or lost. Today, the "W" flag has transcended its practical origins to become the most recognizable victory symbol in baseball. Cubs fans fly "W" flags from their homes, cars, and businesses after wins, creating a visible network of celebration across Chicago and beyond. During the 2016 postseason run, "W" flags appeared in windows across the entire city.

The Rooftop Experience

One of the most unique features of Wrigley Field is the rooftop seating on residential buildings along Waveland and Sheffield Avenues. Because Wrigley is embedded in a dense urban neighborhood, the apartments and buildings beyond the outfield walls have a direct view of the playing field. For decades, residents and entrepreneurs have offered rooftop viewing as an alternative to in-stadium seating, complete with food, drinks, and an elevated perspective on the game. The rooftop experience is a quintessentially Cubs tradition — a reflection of the intimate, neighborhood-embedded character of Wrigley Field that no modern stadium can replicate.

The Ivy Walls

The ivy-covered outfield walls of Wrigley Field, planted in 1937 by Bill Veeck Jr., are the most iconic feature of any baseball stadium. The green ivy in summer, turning to bare brown vines in October, has been the backdrop for countless historic moments and is the single most photographed element of the Cubs experience. For fans, the ivy represents the continuity and timelessness of Wrigley Field — a living element of the stadium that changes with the seasons but endures year after year, just like Cubs fandom itself.

Wrigleyville Bar Culture

The neighborhood surrounding Wrigley Field — known as Wrigleyville — is home to some of the most famous sports bars in America. Murphy's Bleachers, the Cubby Bear, and Sluggers are institutions where fans gather before and after games, where televisions show every Cubs game year-round, and where the memories of great seasons and terrible ones are shared over drinks. On game days, Wrigleyville transforms into a street festival, with fans spilling out of bars and onto the sidewalks in a celebration of community that is as much a part of the Cubs experience as the game itself.

Visiting Graves After 2016

One of the most poignant traditions to emerge from the 2016 World Series victory was fans visiting the graves of deceased family members to share the news. Across Chicago and the Midwest, Cubs fans brought "W" flags, baseballs, and Cubs hats to cemeteries, placing them on the graves of parents, grandparents, and friends who had died without seeing the Cubs win. This spontaneous act of remembrance — connecting the living and the dead through a shared dream finally realized — captured the emotional depth of Cubs fandom like nothing else could.