Chicago Cubs: A history of the beloved ‘W’ flag on the North Side

After William Wrigley Jr.’s death in 1932, his son, Philip K. Wrigley took control of the team and ballpark. He is the person responsible for the Cubs’ center-field scoreboard and upgrades around the park. He added new bleachers, ivy to the outfield walls and the large flagpole.
He was adamant about not adding lights to Wrigley, but did allow a special set of lights to be added to the scoreboard according to Kori Rumore of the Chicago Tribune:

"“There was only one promotional gimmick I ever got away with. Mr. Wrigley permitted me to install lights on top of the flagpole to let homeward-bound elevated passengers know whether we had won or lost that day. The flagpole was on top of the new scoreboard, and at its summit I put a crossbar with a green light on one side and a red light on the other. The green light told the El passengers we had won, the red that we had lost.”"

A 1938 photo marks one of the first images of the ‘W’ flying above the scoreboard at Wrigley Field. The flag, like the earlier Wilmington Ferry flag was blue with a white ‘W’. In 1946, an old game program showed the blue flag with white ‘W’ on the cover but this time accompanied by a white flag with a blue ‘L’ on it. This is the first time the ‘W’ was put with an ‘L’ to symbolize win or loss.