Fly The W: A Guide To The Cubs' Victory

Nick Leason

-Oct 10, 2025

The "Fly the W" phenomenon, deeply intertwined with the Chicago Cubs' historic 2016 World Series victory, signifies more than just a baseball win. It embodies the end of a 108-year championship drought, a testament to perseverance, and a rallying cry for the city of Chicago. Understanding its origins and cultural impact reveals a powerful story of hope, resilience, and collective joy.

Key Takeaways

The "Fly the W" tradition began with the Chicago Cubs' scoreboard flag, signaling a win.
It gained immense popularity and cultural significance following the Cubs' 2016 World Series victory, ending a 108-year drought.
The phrase became a symbol of hope, perseverance, and Chicago pride.
Its roots trace back to the early 20th century, evolving with the team's fortunes.
"Flying the W" now extends beyond baseball, representing overcoming challenges and celebrating success.

Introduction

When the Chicago Cubs win, a simple white flag with a blue 'W' is raised above Wrigley Field. This has been a tradition for decades, but it exploded into a city-wide, national, and even international phenomenon following the Cubs' unforgettable 2016 World Series championship. "Fly the W" became more than just a slogan; it was a mantra, a symbol of hope realized after 108 long years of waiting. This article delves into the origins, meaning, and lasting impact of "Fly the W," exploring how a simple flag became an enduring emblem of victory and perseverance for the city of Chicago and its devoted baseball fans.

What is "Fly the W" and Why is it Significant?

At its core, "Fly the W" refers to the practice of raising a white flag with a blue 'W' on the flagpole at Wrigley Field, the home ballpark of the Chicago Cubs, whenever the team wins a game. A blue 'L' flag is flown when the team loses. This simple visual cue has been a part of the Cubs' identity for decades, allowing fans inside and outside the stadium to know the outcome of the game.

However, the significance of "Fly the W" was amplified exponentially in 2016. For 108 years, the Cubs had been unable to capture a World Series title, a drought that had become a defining characteristic of the team's history and a source of deep frustration for generations of fans. When the Cubs finally broke this curse, defeating the Cleveland Indians in a dramatic seven-game series, the act of "Flying the W" transformed.

It became a powerful symbol:

Of Accomplishment: It represented the culmination of years of effort, rebuilding, and unwavering fan support.
Of Hope Realized: For those who had only heard stories of past glories or lived through decades of losses, it was a tangible sign that the impossible had happened.
Of Unity: The shared experience of watching the Cubs finally win brought the city of Chicago together in unprecedented celebration.
Of Perseverance: It resonated with the idea of never giving up, a message applicable far beyond the baseball diamond.

The "W" flag transcended its original purpose to become a cultural touchstone, appearing on merchandise, in social media posts, and as a general expression of success and overcoming adversity throughout the United States.

The Origins and Evolution of "Fly the W"

While the 2016 World Series cemented "Fly the W" in popular culture, the tradition itself is much older. The use of flags to denote game outcomes dates back to the early 20th century, although the specific design and consistent implementation have evolved over time. — 14-Day Reno Weather Forecast: Plan Ahead

Early Days:

The practice of flying a flag from the Wrigley Field scoreboard to indicate a win or loss is believed to have originated in the 1930s or 1940s. Initially, the flags were likely simpler, perhaps just colors indicating the home team's performance. The now-iconic blue 'W' on a white field and the corresponding red 'L' on a blue field became standardized over the years, solidifying their place in baseball tradition.

The Long Drought:

For decades, the 'W' flag flew, but often it felt like a symbol of past glories or fleeting hopes rather than consistent success. The Cubs experienced prolonged periods of mediocrity and heartbreak, making the 'W' a familiar sight but rarely one associated with ultimate triumph. Fans learned to interpret the flag, but the ultimate prize remained elusive.

The Modern Era and Rebuilding:

In the 21st century, particularly under the ownership of the Ricketts family starting in 2009, the Cubs embarked on a significant rebuilding process. This involved strategic drafting, savvy trades, and eventually, the development of a core group of talented young players. As the team began to show promise, the 'W' flag started to represent not just a single game's victory, but the steady march towards a larger goal.

2016: The Pinnacle:

The 2016 season was the crescendo. Every 'W' flag raised throughout the regular season and the playoffs carried the weight of 108 years of history. When the final out was recorded in Game 7 of the World Series, the 'W' flag flying over Wrigley Field was no longer just a signal of a baseball game won; it was the ultimate emblem of a dream achieved. The sheer relief, joy, and disbelief that swept through Chicago were channeled into the phrase "Fly the W," making it an instant legend.

Post-2016:

Even after the championship, the "Fly the W" tradition continues. It honors the Cubs' victory and reminds fans of what was achieved. Furthermore, it has become a broader cultural expression. People outside of Chicago, and even those not specifically Cubs fans, have adopted the phrase and the sentiment to celebrate their own victories, big or small, and to signify overcoming challenges.

How to "Fly the W" (Beyond Wrigley Field)

While the original "Fly the W" happens atop Wrigley Field, the spirit of the tradition has extended far beyond its physical location. Fans have adopted "Fly the W" as a personal mantra and a way to celebrate success in various aspects of life.

1. Displaying Cubs Pride:

Merchandise: The most common way fans "Fly the W" is by purchasing and wearing Cubs merchandise featuring the 'W' logo – hats, t-shirts, flags, and banners.
Home Decorations: Many fans proudly display Cubs flags or banners with the 'W' on their homes, cars, or during tailgating events.
Social Media: Sharing photos of yourself wearing Cubs gear, at a game, or simply celebrating a Cubs win online often includes the hashtag #FlyTheW.

2. Celebrating Personal Victories:

The "Fly the W" concept has been embraced as a metaphor for celebrating any significant achievement or overcoming a difficult situation. It signifies a "win" in life. — North Port, FL Weather Radar: Live Updates & Forecast

Personal Milestones: Graduating, getting a new job, celebrating an anniversary, or achieving a fitness goal are all moments where someone might feel inspired to "Fly the W."
Overcoming Challenges: Surviving a tough period, completing a difficult project, or navigating a personal crisis can also be framed as a "W" moment.
Community Support: Friends and family might use the phrase to encourage each other or acknowledge a shared success.

3. The "W" Flag Tradition:

Some dedicated fans might even purchase their own Cubs 'W' flags to fly at their homes on game days or after a win, mimicking the tradition at Wrigley Field.

Understanding the Context:

When someone says "Fly the W," they are usually referencing a victory, success, or a positive outcome. It's a concise and recognizable expression of triumph, deeply rooted in Chicago Cubs lore but understood more broadly as a symbol of winning.

Examples and Use Cases of "Fly the W"

The "Fly the W" phenomenon has permeated various aspects of culture, especially within Chicago and the broader sports landscape. Here are some notable examples and use cases:

1. The 2016 World Series Victory:

This is the quintessential example. The image of the 'W' flag flying triumphantly over Wrigley Field after the final out of Game 7 is iconic. It represented the end of the longest championship drought in North American professional sports history. The city of Chicago erupted in celebration, with "Fly the W" becoming the unofficial slogan of the victory parade and the ensuing months.

2. Sports Celebrations Beyond Baseball:

While originating with the Cubs, the sentiment of "Fly the W" has been adopted or echoed by other sports teams and fans to celebrate their own successes. It captures the universal desire to acknowledge and celebrate a win.

Chicago Sports: Other Chicago teams have seen their fans adopt similar rallying cries or celebrate victories with a "W" mentality, drawing parallels to the Cubs' success.
General Sports Fan Culture: Any significant sports victory can evoke the feeling of "Flying the W," whether it's a local team's championship or a national team's major win.

3. Non-Sporting Achievements:

The phrase has transcended sports to become a popular idiom for celebrating any kind of success or overcoming adversity.

Personal Achievements: Individuals use it to mark personal milestones like career advancements, academic achievements, or overcoming health challenges. For instance, after a successful surgery, a patient might say, "We flew the W today."
Business Success: A company that lands a major client, launches a successful product, or achieves a financial target might internally "Fly the W."
Community Events: A successful community fundraiser or the completion of a large public project could be celebrated with the "Fly the W" spirit.

4. Cultural References:

"Fly the W" has been featured in:

Music: Songs and jingles have been created referencing the phrase.
Media: News outlets frequently used the phrase during the 2016 season and beyond when discussing the Cubs or Chicago sports.
Art and Design: The 'W' logo itself has become a recognizable design element, appearing in artwork and fan-made creations.

5. A Symbol of Resilience:

Perhaps the most profound use case is its representation of resilience. The Cubs' journey involved numerous setbacks and near misses over more than a century. The eventual triumph made "Fly the W" a potent symbol for anyone facing long odds and demonstrating perseverance. It's a reminder that persistent effort can lead to ultimate victory. — Yankees Game Today: Schedule, Time, & Where To Watch

Best Practices and Common Mistakes When Using "Fly the W"

While "Fly the W" is a widely understood and embraced concept, especially among baseball fans and in Chicago, there are nuances to its usage and potential pitfalls.

Best Practices:

Understand the Origin: Always acknowledge that the phrase originates from the Chicago Cubs' tradition of flying a 'W' flag after a win, and particularly its iconic status following the 2016 World Series.
Context is Key: Use it appropriately. It's most fitting to describe a victory, success, achievement, or overcoming a challenge. It's a positive affirmation.
Embrace the Spirit: Beyond just the Cubs, appreciate its broader meaning of perseverance, hope, and collective celebration. It’s about shared joy and the satisfaction of accomplishment.
Respect the Legacy: Especially in Chicago, the phrase carries significant emotional weight tied to a historic moment. Use it with genuine enthusiasm rather than trivializing its deeper meaning.
Visual Representation: When applicable, use the actual 'W' imagery (e.g., on merchandise, in digital graphics) to reinforce the connection, but ensure it’s done respectfully.
Hashtag Usage: On social media, #FlyTheW is a common and effective way to connect with others celebrating similar sentiments or Cubs victories.

Common Mistakes:

Misattributing the Origin: Using the phrase without understanding it comes from the Chicago Cubs can lead to confusion, especially outside of sports contexts.
Overuse or Trivialization: Applying "Fly the W" to every minor event or insignificant occurrence can dilute its impact and meaning. It should ideally represent a meaningful win or success.
Using it for Losses: This is the most obvious mistake. The 'W' explicitly stands for a win. Confusing it with a loss or using it ironically in a negative context (unless very clear and humorous) can be jarring.
Lack of Cultural Awareness: While it has spread, its deepest resonance is within the context of the Cubs' specific history and Chicago's sports culture. A lack of awareness might lead to awkward or misplaced usage.
Commercial Misappropriation: Unauthorized or disrespectful commercial use of the Cubs' 'W' logo or the phrase can lead to legal issues and alienate fans.

By adhering to these best practices, you can effectively use and appreciate the "Fly the W" tradition and its powerful message of victory and perseverance.

FAQs

Q1: What exactly does "Fly the W" mean?

"Fly the W" refers to the tradition of raising a white flag with a blue 'W' on the flagpole at Wrigley Field, home of the Chicago Cubs, to signify a Cubs victory. It has evolved into a broader cultural symbol of success and overcoming challenges.

Q2: When did "Fly the W" become popular?

While the flag tradition is old, "Fly the W" gained widespread popularity and cultural significance following the Chicago Cubs' historic 2016 World Series championship, which ended a 108-year drought.

Q3: Is "Fly the W" only about the Chicago Cubs?

Primarily, it originates with and is strongly associated with the Chicago Cubs. However, the sentiment of celebrating a victory or success using the phrase "Fly the W" has transcended the team and is often used metaphorically for any achievement.

Q4: What is the opposite of "Fly the W"?

The opposite is "Fly the L," which involves raising a blue flag with a red 'L' on the Wrigley Field flagpole to signify a Cubs loss.

Q5: Can I "Fly the W" for my own achievements?

Absolutely. The spirit of "Fly the W" has been adopted to celebrate personal victories, career milestones, or overcoming difficult situations. It serves as a metaphor for achieving a significant success or win in life.

Q6: Where did the "W" flag tradition start?

The tradition of using flags to indicate game outcomes at Wrigley Field is believed to date back to the 1930s or 1940s, though the specific design and consistent use evolved over time.

Conclusion

The simple act of raising a 'W' flag over Wrigley Field has blossomed into a powerful cultural symbol, deeply etched in the heart of Chicago and resonating far beyond. "Fly the W" is more than just a sports tradition; it's a testament to endurance, a celebration of hard-won success, and a rallying cry for perseverance. Whether celebrating a Cubs victory or marking a personal triumph, the spirit of "Fly the W" reminds us that even after long waits and many challenges, victory is possible and worth celebrating with all our might.

Ready to celebrate your own victories? Share your "Fly the W" moments with us and connect with a community that understands the thrill of success!

Last updated: October 26, 2023, 10:00 UTC