“Fly the W” is a Chicago Cubs slogan and tradition that means celebrating and displaying a win by the team.

Core meaning

  • The “W” stands for “win,” just like in a win–loss record in baseball.
  • After a Cubs victory, a white flag with a big blue W (the “Win Flag”) is raised or displayed, and fans say or post “Fly the W!” to show the team has won.
  • Online, “Fly the W” is also used as a hashtag or phrase by Cubs fans to cheer, brag a bit about a victory, and share in the celebration.

Where it comes from

  • At Wrigley Field, the Cubs have long flown flags after home games: a W flag for a win and an L flag for a loss so people passing by could tell the result.
  • The specific phrase “Fly the W!” and the hashtag #FlyTheW took off in the 2010s, becoming a rallying cry widely promoted by the team and its fans.

How people use it now

  • Fans might:
    • Hang a W flag at home or on their car after a win.
* Post “Fly the W” or “#FlyTheW” on social media with score graphics, memes, or photos from the game.
  • In casual internet slang more broadly, W can just mean “win” or “dub,” so “Fly the W” fits that same idea: proudly showing off a victory.

In short, if you see “Fly the W,” it almost always means Cubs fans are celebrating a win and literally or figuratively raising that W flag.

TL;DR: “Fly the W” = Cubs win, raise the W flag, and celebrate together.

Information gathered from public forums or data available on the internet and portrayed here.