Column: Trolling the Chicago Cubs with an ‘L’ flag backfires on Milwaukee Brewers with NLCS flop

The Milwaukee Brewers learned a valuable lesson last week.

Don’t mess with the “L” flag.

It might have been a coincidence that the Brewers were swept in four games by the Los Angeles Dodgers in the National League Championship Series after taking a team photo with the “L” flag following their division series-clinching win over the Chicago Cubs.

The “L” flag did not factor into any of Shohei Ohtani’s three majestic home runs Friday in the Dodgers’ NLCS-clinching win, or any of Ohtani’s 10 strikeouts over six scoreless innings. And surely the “L” flag had nothing to do with one of their fans losing her job after going viral for threatening to call ICE on a Dodgers fan who happened to be a United States citizen and a veteran of two wars.

But considering all the bad things that happened to the team with the best record in baseball after the “L” flag incident at American Family Field, it makes you wonder.

The “L” flag, for those not paying attention, is the sad cousin to the “W” flag, which Cubs fans fly at Wrigley Field after wins. The tradition began in the 1930s when the Cubs began flying a “W” or “L” flag atop of the center-field scoreboard to let riders on the ‘L’ know whether the team had won or lost that day.

It was a tradition that few players thought about until 1998, when Cubs closer Rod Beck suggested flying the “L” flag was “bad karma.”

“I’m not blaming anything for it,” Beck said. “But I’m a believer in positive energy and karma. When you lose a ballgame and fly an ‘L’ over the park, you leave a bad aura around the ballpark and it can go all the way into the next day.

“They do it, obviously, so the people on the (train) can see whether we won or lost. It’s a good theory, but maybe they can change it to where they can drive by and when they don’t see any flag they can assume it’s an ‘L.’ Or maybe they can fly a `W’ for “Wanted to win.”

Beck was not serious, but he was a man who enjoyed stirring debate.

“It’s not a strong theory,” he told me. “But it’s something to make you think.”

Column: Trolling the Chicago Cubs with an ‘L’ flag backfires on Milwaukee Brewers with NLCS flop
Fans watch during the fifth inning of Game 4 of the National League Championship Series between the Brewers and Dodgers on Friday, Oct. 17, 2025, in Los Angeles. The Dodgers won 5-1 to sweep the best-of-seven series. (Mark J. Terrill/AP)

Beck’s suggestion was widely ignored until 2008, when the Cubs marked the 100th anniversary of their last championship season and had a team that was good enough to end the drought. In July of that season, with the Cubs in first-place, team executives considered the idea of not flying the “L” flag after losses but decided to leave the tradition intact. Instead of blaming the flag, they turned their attention to the Billy Goat curse.

Before Game 1 of the 2008 NLDS against the Dodgers at Wrigley Field, unbeknownst to general manager Jim Hendry and manager Lou Piniella, Cubs executives Crane Kenney and Mike Lufrano invited a Greek Orthodox priest onto the field for a pregame ceremony to bless the Cubs dugout with holy water and remove the curse.

Long story short — it didn’t work.

“Now I’m just another Cubbie occurrence,” the priest, Rev. James Greanias, told the Chicago Tribune that night.

The Cubs were swept in three games by the Dodgers and would not get back to the playoffs for seven years.

The “L” flag went back into semi-obscurity until 2017, when Brewers fans began bringing them to what was then named Miller Park in response to a mass migration of Cubs fans to their ballpark for Cubs-Brewers games. It really took off in 2018, as the Cubs-Brewers rivalry began to heat up under Brewers manager Craig Counsell.

Column: Trolling the Chicago Cubs with an ‘L’ flag backfires on Milwaukee Brewers with NLCS flop
Brewers fans display an “L” flag after the Brewers defeated the Cubs in Game 5 of the NL Division Series on Oct. 11, 2025, at American Family Field in Milwaukee. (Chris Sweda/Chicago Tribune)

But trolling the Cubs was typically something done by fans, not the players.

After the Brewers beat the Cubs last week in Game 5 of the NLDS, the Brewers brought an “L” flag to the field, and reliever Trevor Megill held it high in the team photo. The Brewers’ X account, @Brewers, then trolled the Cubs by tweeting the photo and creating an AI-generated video of an “L” flag covering the iconic Bean, adding the caption “HEY CHICAGO, WHADAYA SAY?”

MLB’s X account, @MLB, added to the story by tweeting their own video with a laughing emoji.

It was all in good fun, though the backlash from Cubs fans suggested many weren’t amused by the trolling. Counsell and Cubs players had congratulated the Brewers and complimented the team after losing Game 5, so to some it seemed like the trolling by Brewers players and the organization’s social media employees was classless and beneath a professional sports team.

Would the Cubs have mocked the Brewers had they won? Doubtful. Would their social media team have piled on? Possibly.

We’ll never know.

Either way, the controversy figured to die down until next season when it would obviously be brought up again when the teams met again. But the Brewers lost the first two games to the Dodgers at home, and their fan who threatened to have a Dodgers fan arrested by ICE quickly became famous. Cubs fans helped amplify the video, which quickly became a national story.

When the Brewers lost Game 3 at Dodger Stadium, more fans jumped in, and included the woman referred to as “Brewers Karen” as part of the “curse of the ‘L’ flag.” Game 4 became an instant classic thanks to Ohtani’s performance, and the Brewers’ dream season ended in disappointment. The team scored four runs and had only 14 hits in the four games.

“The pitching performances by the Dodgers basically put the hammer down,” Brewers manager Pat Murphy said afterward.

True enough. The Dodgers were the superior team and proved it in the NLCS. They’ll head into the World Series as favorites over the Seattle Mariners or Toronto Blue Jays, and MLB can only pray the series isn’t as short and lopsided as the NLCS turned out to be. A ratings flop seems inevitable if it’s another sweep.

The “L” flag will no doubt return to American Family Field when the Cubs and Brewers play there in 2026, and it’s now part of Brewers team lore, just as the curse-busting episode of 2008 became part of the Cubs lore.

Kenney later called it “one of the dumbest things” he had ever done, taking blame. Will Megill and the Brewers ever admit that holding up an “L” flag for a team photo was one the dumbest things they’ve ever done?

Check back in spring training.

Related Posts

🚨 PLANS IN QUESTION: The New York Yankees are facing growing scrutiny after a key slugger made a revealing World Baseball Classic decision. What was already unclear now feels louder and harder to ignore. Fans and insiders are asking the same thing: what exactly is the plan here? And this moment may expose more uncertainty than the Yankees intended.

The New York Yankees remain locked in an uneasy holding pattern this offseason, but Jazz Chisholm Jr. has given fans and executives alike something new to consider…

🚨 INSIDE INTEREST: The Chicago White Sox are reportedly circling a former All Star outfielder, and the timing is raising eyebrows across the league. What looks like a low-key offseason check could turn into something far more serious. Fit, opportunity, and motivation suddenly align in an intriguing way. If Chicago pulls the trigger, this move could quietly reshape their lineup outlook.

The MLB offseason has officially shifted into high gear, with the hot stove blazing across the league after two blockbuster deals reshaped the market in rapid succession….

🚨 MONEY ON THE TABLE: Newly surfaced financial statements suggest the Atlanta Braves have far more spending power than they’ve let on. The numbers paint a picture that clashes with years of conservative messaging. Insiders are now questioning whether restraint was strategy, not limitation. And this revelation could completely change expectations for Atlanta’s next big move.

Delta Air Lines closed the book on its centennial year with a financial performance that underscored its status as the most profitable airline in the United States,…

🚨 FIRM DECISION: The Boston Red Sox have reportedly drawn a clear line regarding Trevor Story heading into the 2026 season. What once felt open ended now sounds far more decisive behind the scenes. Insiders say this stance wasn’t reached lightly. And it could quietly reshape Boston’s infield future sooner than expected.

The Boston Red Sox have quietly resolved one of their most important positional questions heading into the 2026 season, confirming that Trevor Story will remain the club’s…

🚨 RIVALRY RAID: The New York Yankees could be lining up a bold move to steal a free agent arm straight from the Baltimore Orioles. What looks like a routine market play carries serious rivalry implications. Insiders believe the fit is cleaner than many expected. If this happens, the balance of power in the AL East could shift quietly but fast.

There is a growing sense of unease surrounding the New York Yankees this offseason, as multiple high-stakes scenarios threaten to unfold in ways that could fundamentally reshape…

🚨 INJURY WATCH: Justin Steele just delivered a major update that instantly shifted the mood around the Chicago Cubs. What sounded uncertain not long ago now feels very different. Fans are reading between every word, trying to understand what this really means for the rotation. And this update could quietly change how Chicago approaches the weeks ahead.

The Chicago Cubs received a significant boost this weekend as the organization continues shaping its pitching blueprint for the 2026 season, with new clarity emerging around one…