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A common sight at PNC Park: a Pirates fan waving the Jolly Roger.
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Pirates or Cubs: Who will wave victory flag tonight?

Gene J. Puskar/Associated Press

Pirates or Cubs: Who will wave victory flag tonight?

Pirates fans hope they will be able to celebrate tonight by hoisting a victory flag over PNC Park. Cubs fans just hope their flag-raising days aren’t over.

Though the two clubs have developed reputations for losing — the Cubs’ World Series drought is more than 100 years old, while the Pirates own a record for consecutive losing seasons — they also are united in a distinct tradition of raising flags after wins.

And, as fate would have it, these two teams meet tonight with a lot more than flags on the line.

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The Cubs and Pirates appear to be the only baseball teams that raise victory flags, said Cassidy Lent, a reference librarian in the Giamatti Research Center at the National Baseball Hall of Fame in Cooperstown, N.Y.

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The Cubs have been at it longer, with a tradition that dates to the late 1930s, when the team started raising “W” flags for wins and “L” flags for losses.

The Pirates’ tradition is much more optimistic, the colors hoisted only after a win. This young tradition began in the years after the Pirates moved to PNC Park in 2001, when broadcast announcer Greg Brown started commanding fans to “Raise the Jolly Roger.” The team, and fans, followed suit. The Pirates raise a black pirate flag on the outfield concourse after victories, and fans bring their own to home and road games.

It wasn’t until the Pirates started winning on a regular basis that fans could really start flexing their flag-raising muscles.

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“When you’ve got a losing team, you’re not raising the flag as often, for one, and people aren’t as invested in the tradition,” said Anne Madarasz, co-director of the Western Pennsylvania Sports Museum at the Heinz History Center. But Pittsburgh fans have always embraced their affiliation with pirate imagery.

“The Pirates are very literal in some of these fan traditions,” she said. The club formerly called the Alleghenies literally “pirated” a free agent from Philadelphia in 1891, and thus became known as the Pirates. Now, raising the skull and crossbones — a move historically employed by seafaring pirates — marks another connection with the team’s buccaneering legacy.

Besides, with a city full of Terrible Towels, “you also have a fan base here that’s conditioned to get behind this sort of thing,” Ms. Madarasz said.

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At Wrigley Field, the W and L flags aren’t the only banners flapping in the Chicago wind: Wrigley’s flag lineup also includes the city and state flags for a visiting team and banners that list the National League standings above the ballpark’s iconic scoreboard.

The flag tradition predates World War II, when in the midst of an extensive renovation to Wrigley Field, team owner Philip K. Wrigley wanted to incorporate Art Deco elements into the design, according to Stuart Shea, author of “Wrigley Field: The Unauthorized Biography.” The ballpark added the simple, elegant W and L flags to inform fans walking around Wrigleyville or traveling home on trains how the team had fared.

At old-school Wrigley, the tradition has stuck, although the color patterns have since switched. These days, a white flag with a blue W signals a win, and a blue flag with a white L laments a loss, though they fly only after home games.

“The Cubs’ flag tradition is very defined and time-honored, and it really is part of the whole aesthetic of Wrigley,” said Todd Radom, a graphic designer who specializes in sports identities. “Aside from beautiful aesthetics and all that, there actually was a reason behind it.”

The Pirates’ Jolly Roger logo and the Cubs’ “W” are licensed by Major League Baseball. Rexene Carlstrom, one of the owners of Wrigleyville Sports — which operates a shop by Wrigley Field, and the Pittsburgh Fan outside of PNC Park — said the W flag is the winner in sales. “I think Chicago is more obsessed, and only because Chicago has a full stadium, win or lose, it doesn’t matter,” she said.

Given the size of Chicago and the longer history of the W flag, perhaps that shouldn’t come as a surprise.

Which flag would she prefer to see on Wednesday night? Her heart lies with the Cubs, but she maintains sympathies for the Pirates.

“I hope they both win,” she said.

First Published: October 7, 2015, 4:00 a.m.

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A common sight at PNC Park: a Pirates fan waving the Jolly Roger.  (Gene J. Puskar/Associated Press)
Chicago Cubs fans hold up a win flag.  (David Zalubowski/Associated Press)
Gene J. Puskar/Associated Press
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