The Cubs spent the better part of the last century as a losing team, so their winning traditions have not been noticed until the past two seasons. But as the Cubs have evolved into the best team in baseball, winning their first World Series since 1908 Wednesday, the tradition of the W Flag has become mainstream. Baseball fans around the world now recognize "Flying the W" as a celebration of a Cubs victory.
It turns out when the flag was initiated in the 1940s, it was not alone. The Cubs also had an L Flag. Based on the outcome of the game -- Wrigley Field did not host a night game until 1988 -- the Cubs would raise the winning or losing flag. Before technology caught up, this was a way for the Cubs to update their fans, as many Chicagoans would ride the Chicago "L" train past Wrigley Field.
