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Since Wrigley’s early investment,  only the Ricketts family has done major renovations to the park. In 2009, they unveiled a major four-phase plan known as the 1060 Project at the cost of $575 million dollars to extensively renovate the old Weeghman Park and bring it into the modern baseball age, while still keeping its historic spirit and the ‘W’ flying above it

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.

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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.

So when waving the ‘W’ after Cubs victories next season, remember that today, the flag means a Chicago Cubs win. However, don’t forget about a California town named Wilmington and how the ‘W’ traveled from the western coast of southern California to the Friendly Confines in Chicago, uniting fans across the country as the Cubs do today.

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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:

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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:

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?”

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Somehow, Banks’ jersey inspired the Cubs house and not long after, the Cubs made two significant changes. First, the Cubs got rid of the ‘L’ flag, as it seemed ridiculous to wave a flag of loss or defeat. Second and most importantly, even historically, they changed the ‘W’ to its current white flag and blue letter design, leaving off the pinstripes.

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In 1982, the first Cubs number to be retired was Ernie Banks and a white flag with blue pinstripes and the number, ’14’ in blue was set on the left-field foul pole. At the time, the Cubs were still using the ‘W-L’ but with the blue background.

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.

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.

The ‘W’ flag and all its predecessors never again did appear in the friendly confines of Wrigley Field, nor did its negative companion the ‘L’.. The colored light signal and large flagpole and many of the original upgrades to the property still reside at the historic North Side park.