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

One of my favorite rituals after any Chicago Cubs victory, whether in town or on the road, is watching countless fans fly their respective ‘W’ flags.

My wife ordered two new ‘W’ flags that arrived this week in the mail. She was thinking the  Chicago Cubs would be cruising in postseason right about now. I had abducted the larger 3×5 ‘W’ flag and hung it my office at work.

My son and daughter came into the room to see what package had arrived in the mail as I pulled out the two new flags. They looked disappointed as they knew the Cubs were not in the postseason. To get their minds off the Cub’ dubious demise, I asked them, “Do you know what the ‘W’ stands for?”

“Wrigley Field,” my 10-year old daughter said quickly.

“No… it stands for win,” my teenage son said.

As I began to unfold the flags I told them the history of the ‘W’ as I had learned it over the years.

In 1919, the famous chewing gum entrepreneur William Wrigley Jr. Wrigley, before owning the Chicago Cubs or its stadium, was a businessman that had purchased Santa Catalina Island in Southern California from the Banning family who had made their fortune in the shipping industry. Kori Rumore of the Chicago Tribune reported:

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“Part of the purchased package was a company that the previous owners had founded in 1884, Wilmington Transportation Co. … all of Wilmington’s vessels flew the white W on a dark blue background,” said Michele Bestudik, historian and film liaison for the Santa Catalina Island Co. Wilmington is a neighborhood along the harbor in Los Angeles.

In 1921, Wrigley purchased the Chicago Cubs and changed the name of the then-Weeghman Park to Cubs Park (in 1926 it was renamed Wrigley Field). Wrigley also changed the team’s headquarters for Spring Training to the newly purchased Catalina Island.

He used the ferries he had acquired to transport the team to Catalina Island and back for practices. The ferries still displayed the Wilmington flag, bearing the blue background and white ‘W’ flag. There are even pictures that show the flag painted on the steam engine smokestack. For the most part, Wrigley liked the flag. It was after all, the first letter of his famous last name and made for an easy transition to his legacy.

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.