The Story Behind "Fly The W"

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The Story Behind "Fly The W"

The Story Behind "Fly The W"

The History of the Cubs' Win Flag


Early 1900's

In the year of 1919, about eight years after the Chicago Cubs’ last World Series win, William Wrigley Jr. bought Santa Catalina Island off the coast of Southern California along with a transportation company, the Wilmington Transportation Co. Each vessel owned by this company flew a flag with a blue field and a white “W”. Years later Wrigley bought the Cubs and moved their spring training to his island where he built a ballpark for them to play. Nearly 20 years later, William’s son, Philip, decided to do some renovations to Wrigley field, including adding the Center Field scoreboard, the ivy to cover the outfield wall, and new bleachers, as well as two lights, red and green, to signal to the Elevated train passengers on their way home if the Cubs had won or lost that day. Some time in the year of 1937 or 1938, during all of the wrigley field renovations, the W flag was first flown over the center field scoreboard to signify a win along with the light.

In 1946, a Cubs program first referenced all of the flags being flown over the scoreboard, including the win/loss flags. At the top of the masthead over the center field score board flew an american flag. In two lines, descending from either end of the crossbar were colored pennants to represent each club in the league, in order of the league standings. And off the arm of the mast flew a flag with a blue field and a white “W” for win or a white flag with a blue “L” for loss, to signify the outcome of that day’s game to fans passing by on the way home from work.

Late 1900's

If you noticed that the colors for the W and L flags were opposite of what they are now, you would be right, it’s not mistake. It wasn’t until the Cubs retired Ernie Banks’ #14 jersey in 1982 that the Cubs decided to permanently switch to switch the colors. After the white pin-striped jersey flag was raised on the left field pole, replacing a blue Chicago Cubs flag, it prompted the team to change the color of the flag to white.

What’s funny is, the change was so insignificant at the time, that the Cubs themselves forgot to change the media guide until Wrigley Field hosted the 1990 All-Star Game; they were revamping the guide in preparation and noticed the error. Over the years, the flag waxed and waned in popularity, with the frequent flying of the L flag through 1997’s abysmal 68-94 season, the flag hadn’t yet peaked in popularity.

Early 2000's

It was in 2003, as the Cubs fought through the NL Central Division race that the “W” became an icon. This is when the phrase “White Flag Time at Wrigley” became a popular phrase to explain Cubs wins. Fans could be seen in the crowds on TV with homemade, makeshift flags using everything from cardboard to golf flags.

Five years later, in 2008, the Cubs won their 10,000th game on April 23, 2008, while playing the Colorado Rockies in Colorado. For this special occasion, the Cubs flew a commemorative “W” flag at Wrigley (an unusual occurrence for a road game to be recognized by the flag). The flag flew until the next game when it was taken down and signed by all of the members of the 2008 Chicago Cubs and auctioned off for charity.


At least as early as the 2015 season, the phrase “Fly The W” began to be used by the team and fans along with the social media hashtag “#FlyTheW” to promote the team. It has been heavily used since and is a battle cry for many supporting the Cubs. When the Mets beat the Cubs in the NL Championship Series that year, some fans mocked the Cubs by turning the “W” rally towels upside down to celebrate.


But in 2016, The Cubs got the last laugh, pulling together a fantastic 103-58 season record, culminating in a 8-6 win in game 7 over the Cleveland Indians in the 2016 World Series. Marking the first time in 108 years that Cubs had won a world series. The last World Series win came prior even to William Wrigley Jr. purchasing Santa Catalina Island and the Wilmington Transportation company and that now iconic, “W” flag.

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