JUMP TO:
- Flying the W meaning
- Who started Fly the W celebration?
- When did Fly the W tradition start?
- What does the W flag look like?
- Is there an L flag for losses?
- How Fly the W became a popular phrase
- Fly the W history
- Fly the W on social media
The Chicago Cubs have one of the deepest and richest histories among all franchises in North American professional sports. With deep history comes tradition.
From the ivy that adorns the Wrigley Field walls to the franchise's pinstripe home uniforms, there are plenty of traditions associated with the Cubs. One tradition, however, has become much more of a phenomenon in the 21st century, though it was established well before that.
The objective in sports is to win ballgames, and one of the Cubs' most storied traditions signifies that they have done just that. As simplicity often gets the job done, the Cubs "fly the W" over Wrigley Field when they emerge victorious.
While it is as simple as flying a W, there is much more to it than that. Here is what it means to "fly the W," and how the tradition became one that will forever be associated with one of the greatest moments in franchise history.
MORE: Most home runs in an MLB Game, from Lou Gehrig to Kyle Schwarber
Flying the W meaning
Flying the W signifies that the Cubs have won a game.
It is a Wrigley Field tradition. After a victory, the "W" flag is flown atop the stadium's scoreboard, high enough for passersby to learn of the game's outcome. If there is a doubleheader, two flags are flown.
MORE: 16 NFL stars you never knew were also drafted by MLB teams?
Who started Fly the W celebration?
Scoreboard operators, in conjunction with the organization, technically started the celebration. In a 1946 game program, the Cubs outlined and explained the meaning of the win/loss flags.
MORE: What is the World Series trophy called?
When did Fly the W tradition start?
The specific date is unknown, but it is believed to have begun in the 1930s, according to the Baseball Hall of Fame.
After the team constructed new bleachers, a hand-operated scoreboard and the recognizable ivy in the 1930s, the “W” flag became a staple icon. The actual date of the first flying of the flag at Wrigley is not known; as there were many changes happening to the park between 1937 and 1938, a new flag apparently never warranted a mention.
MORE: Everything to know about MLB attendance records
What does the W flag look like?
The W flag is a white flag with a blue "W" on it.
Is there an L flag for losses?
Yes, there is an L flag for losses. The flag that denotes losses is a blue flag with a white letter "L" on it.
If the Cubs split a doubleheader, one "W" flag and one "L" flag are flown.
Fans of the Cubs' rival teams have often taken a liking to the "L" flag to add to the competition. In 2019, Milwaukee's Central Distillery reintroduced L Flag Bourbon, with its label mirroring the Cubs' flag used to signify losses.
How Fly the W became a popular phrase
In raising a "W" for wins, it quickly became a tradition synonymous with victory and success. It took on new life during the Cubs' historic run to a World Series title in 2016, as it was a rally symbol for their fanbase.
The "W" flag raised outside of Wrigley Field after Game 7 of the 2016 World Series was the first that commemorated a title.
Fly the W history
The history of flying the W dates back to the Wrigley family's purchase of Catalina Island in California. The purchase came with the Wilmington Transport Company, and ships ferried fans and players to the team's Spring Training location on Catalina Island.
Those ships bore a blue flag with a white "W."
In the 1930s, that "W" flag became a trademark of the lore around Wrigley Field, as scoreboard operators would raise a "W" flag for Cubs wins and an "L" flag for losses. As such, those in and around the neighborhood who did not attend the game could easily learn the outcome.
Initially, the color schemes were reversed: the win flag was a white "W" on a blue background, while the loss flag was a blue "L" on a white background. In the 1980s, the color scheme was changed to what they are today, as the blue "W" on a white flag matches the white flags raised to honor the franchise's retired greats, whose numbers are embroidered in blue.
The tradition quickly caught on and has been a trademark for decades running.
MORE: What is the World Series trophy called?
Fly the W on social media
The phrase "Fly the W!" has been used by the Cubs to signify wins across social media since at least the 2015 season. The saying has also come with other social media-specific elements.
Fly the W gif
However simple, the Cubs share an animated version of the "W" flag to social media after wins.
CUBS SWEEP!
— Chicago Cubs (@Cubs) September 28, 2025
Final: #Cubs 2, Cardinals 0. pic.twitter.com/BTZOE1I8Jb
Fly the W hashtag
The #FlyTheW hashtag is often accompanied by a hashflag on X (formerly Twitter). In adherence with tradition, the hashtag is typically used after wins.
Cubs' victory graphics also feature a stylized "W" flag.
THE MOMENT. #FlyTheW pic.twitter.com/M5hRqecb6A
— Chicago Cubs (@Cubs) October 3, 2025
MORE: Ranking the 9 worst renditions of 'Take Me Out to the Ball Game'