For the last three seasons I have made it a Facebook custom to post the blue and white W Flag along with a pithy one or two sentence game re-cap as if delivered by the hokiest radio sports guy every time the Chicago Cubs win a game. I don’t get the opportunity enough, but as a Cubs fan always hope for more opportunities and dream of the day I can post it for the last game played in post season October.
Cubs fans and other Chicagoans—even Sox fans who mock it—know what the flag means. But it seems to confuse the crap out of others. What does the W mean and what does it have to do with the Cubs, I am asked. Allow me to explain.
In 1937 Cubs owner P. K. Wrigley ordered a major renovation to his already aging stadium. Under the supervision of club President William Veek, the bleachers were torn down and replaced and a huge manually operated Score Board was erected over center field. The scoreboard was topped with a naval style flag mast with signal style flags flying from the cross arms, perhaps a tip of the hat to the sail boats in nearby Lake Michigan which could be seen from the lofty heights of the scoreboard on a clear summer day. With the American Flag snapping from the top of the mast, on game days flags representing Major League teams were flown below the cross arms—National League on one side, American League on the other—in order of their place in Pennant races.
By the way, the same year Veek’s son Bill Jr., a junior executive with the club, busied himself planting ivy along the brick walls of the outfield. Thus in 1937 the two Veeks created the signature look of Wrigley Field beloved to this day.
Shortly after the erection of the mast, it became customary to hoist flags—a W for a win or an L for a loss—on game days after the League flags were hauled down. These were intended to signal the outcome of game to the surrounding neighborhood and especially to commuters coming home from work on the crowded EL running across Sheffield Avenue.
Legend has it that this continued an informal and intermittent tradition of some sort of signals hosted by players, club housemen, or grounds keeps even earlier sometimes using a towel or even a red bandana. But the new professionally made flags were the first official use by the club.
Originally the W flag was Cubs blue with the letter in bold white while the L flag reversed the colors. At first they were flown only for home games, but by the 1950’s were being hosted to report the outcome of away games as well.
Because the flags were hauled down along with the American flag at sunset, Veek Jr. also installed some lights to use for the same purpose at night along the yard arm of the mast, blue for a win, white for a loss. Later the lights were moved to the top of the scoreboard. The lights are still in use, but most people don’t notice them or know what they stand for.
That is definitely not the case with the W flag. Especially during the Cubs famed but doomed Pennant run in 1969.
In the ‘80’s the team retired the numbers of first Ernie Banks and then Billy Williams flying them as flags from the Foul Poles. The flags featured the players’ numbers against a background of the Cubs home uniform pinstripes. Other Cub greats, Ron Santo, Ryne Sandberg and Ferguson Jenkins/Greg Maddux—they wore the same number—were added. The W flag was changed to blue on white to match those flags, and the L flag was similarly reversed.
Interest in the flags really took off in 2003 when the Cubs won the Central Division Championship. Fans began to bring homemade reproductions to the ball park hoping to catch the eye of WGN-TV camera crews.
The team, always a champion of merchandising was soon offering the flag for sale in several sizes, including a car radio antennae version and decorating other merchandise like coffee mugs, mouse pads, T-Shirts, and neck ties with the blue W.
About the same time broadcasters began using the expression “raising the white flag” at Wrigley to denote a Cub win.
Being a devoted Cub fan, I began posting the flag in my win notices on Facebook. And no, I don’t post the L Flag.