A large gathering of mostly men crowded into a bar in Chicago’s Lakeview neighborhood Wednesday night, but a majority of them were not there to cheer on the Cubs in Game 2 of the World Series.
Instead, they watched dozens of drag queens — both veterans and rookies — perform at Sidetrack for an event billed as “Dragapalooza.”
“We’re still showing the game upstairs right now,” said Sidetrack general manager Brad Balof, who was dressed in a sparkly pink dress as his drag alter-ego, Missex. “Anybody who’s in the building now enjoying ‘Dragapalooza’ can go upstairs any time and check the game out up there.”
Most of the patrons stuck with the drag queens.
Sidetrack, which is one of Chicago’s largest gay bars, sits at one of the busiest intersections in Boystown, an area of the Lakeview neighborhood that is the center of the city’s LGBT community. Sidetrack is also just a few minutes away from Wrigley Field and the scores of sports bars that make up the ground zero for Cubbie fever in Wrigleyville.
These two sections of Lakeview are usually a bonanza during the weekend near Halloween, with women and men bar-hopping and, for some, wearing costumes that involve as little clothing as possible.
But on top of the typical Halloween hjinks this year, the Cubs and Cleveland Indians will be in town Friday, Saturday and Sunday for the World Series, an event the Lakeview neighborhood hasn’t hosted in 71 years. This rare occasion has some local residents and business owners feeling a mixture of emotions — from excitement the Cubs could win the World Series for the first time in 108 years to anxiety over what kind of havoc could be unleashed by such a feat.
“Halloween is a huge gay holiday,” said drag queen Trannika Rex, who co-hosted “Dragapalooza” at Sidetrack. “So all of the gays are going to be out, and then all of the straight people are going to be out, and you worry about having two hordes of people directly next to each other at their supreme drunkest.”
Trannika Rex hosts a drag show every Saturday at the nightclub Berlin, which is not far from Wrigleyville. The show helped start the drag careers of Kim Chi and Pearl, two queens who competed in RuPaul’s Drag Race, which is like the World Series of drag.
Because of Trannika Rex’s high profile within the city’s drag community, some of her fans might consider her as an MVP, but she said she sees herself more like a Harry Caray.
Her knowledge of sports, she admitted, needs a touch-up.
“I heard they were in the Stanley Cup this year, so I’m really excited,” Trannika Rex said. “But other than that, I don’t know anything.”
When the Cubs beat the Los Angeles Dodgers last Saturday for a spot in the World Series, Trannika Rex said some baseball fans made a rare appearance at her show and caused some alarm among the queens.
“I just don’t want to be anywhere near the Cubs, especially in makeup and holding wigs and stuff,” she said. “I just want to be in my safe zone at Berlin, hiding.”
Joon Lee, who performs in drag under the moniker Joonage A Trois, said he believes the avalanche of baseball fans descending into Lakeview during the weekend could be problematic.
“Oftentimes they’re drunk and rowdy and homophobic,” he said. “So it’s a little bit dangerous for drag queens this weekend.”
Cubs spokesman Julian Green said he has never heard concerns about homophobia from fans, adding that many people who flock to Wrigley Field admire the diversity of the area surrounding the ballpark.
“They’re fathers and grandfathers who know this community and have come to this community for a long time,” he said. “They respect the tradition and heritage of the ballpark and the neighborhood around it. … Certainly you may have instances of people who don’t know how to behave, but it’s not reflective of this fan base.”
To help keep the peace during the World Series, more than 1,000 police officers, Illinois troopers, Cook County Sheriff’s deputies and agents from the FBI and Homeland Security will be deployed to the neighborhood, according to Chicago Police Supt. Eddie Johnson.
Some businesses, however, are not as optimistic that the large police presence will be enough to keep exuberant fans in check. Less than a block from Wrigley Field, wooden boards cover up the large glass windows of a convenience store. A man behind the store’s counter, who refused to give his name, said he was concerned someone would break the windows.
That’s a situation Eric Kirsammer knows too well. Kirsammer is the owner of Chicago Comics, a comic book store near Wrigleyville. He said two men got into a fight outside the store a few years ago and one of them was slammed into the store’s window, which broke and cut the man’s head.
“As we were watching him, he started bleeding more and more,” Kirsammer said. “It was kind of horrifying. And he’s like, ‘What’s going on?’ And we’re like, ‘The ambulance is coming.’ And he’s like, ‘Oh, I’m OK.’ And we’re like, ‘No, you’re not. You’re bleeding all over the place.’ But that was a nightmare.”
To make sure there are no mishaps during the World Series, Kirsammer said he plans on being inside the store during the games Friday, Saturday and Sunday.
But not all baseball fans cause problems for Chicago Comics, Kirsammer said. One time, a man with liquid courage came into the store after a ballgame and had his eyes set on an expensive replica of Thor’s hammer, Kirsammer said. The man’s friends and the store’s employees tried talking the drunk man out of spending hundreds of dollars on the prop, Kirsammer said, but he would not listen.
“We still laugh, thinking about him waking up the next day with probably a broken, 200 and some dollar hammer,” Kirsammer said.
The comic shop owner and other businesses said they believe the city is doing the best it can to prepare for the World Series
Having more first responders in the area will help add a level of safety and mindfulness, said Shawn Hazen, the special events and marketing manager at Roscoe’s, a gay bar in Boystown that has a makeshift ivy wall outside with a light-up W for the World Series.
Hazen, a lifelong Cubs fan, said having the World Series coincide with the Halloween weekend could make for a great celebration.
“We all say once in a lifetime,” he said. “We hope it’s not a once in a lifetime event. Maybe this will be a new pattern for the Cubs.”
Green, the Cubs spokesman, said that is the team’s goal.
Hunter Clauss is a digital editor for WBEZ. You can follow him @whuntah.