The "Fly the W" phrase and the "W" symbol refer to a longstanding tradition of flying a "Win Flag" at Wrigley Field after the Chicago Cubs win a game. The flag features a large blue letter "W" on a white background and is raised immediately after a Cubs home game victory to signal the win to fans and passersby, including those on nearby transit lines. This tradition dates back to the late 1930s and has become an important and iconic symbol for Cubs fans, representing celebration and success. The expression "Fly the W" and its accompanying hashtag #FlyTheW have been widely promoted by the team and embraced by fans as a rallying cry for Cubs victories. The "W" flag contrasts with an "L" flag, which is flown after Cubs losses, with color schemes that switched around the 1980s to avoid negative associations. The use of the "W" flag is deeply tied to Cubs history and fan culture.
