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SKOKIE —  Hundreds of CTA employees converged at the agency’s cavernous rail maintenance building in suburban Skokie on Sunday for the transit agency’s annual Jamboree event. 

The event allows the CTA’s more than 10,400 employees to show off their skills in front of co-workers, family and friends. The winners of each department’s respective competitions — which include navigating an obstacle course with a bus, cleaning graffiti off CTA property or using a cutting torch to split an iron rail — is awarded extra paid time off, a trophy and cash prize. 

“It’s an opportunity for employees at the authority to show their families what they do here, especially our folks in operations,” said CTA project coordinator Cee James. “When they work these long hours, you’re not always sure what’s going on. Fixing trains or doing this or that. This lets them actually be in the shop and see how things go down and how massive these things are and how much work goes into it.” 

While most Chicagoans may be familiar with CTA bus and train drivers and repair crews out on the tracks, Sunday’s event also tested janitorial staff with timed competitions that included sweeping up sand, removing stickers from window panels, scrubbing graffiti and even cleaning mock biohazards. 

Emmett Hasey mops up oatmeal during a challenge on Saturday, Sept. 13, 2025, in Skokie. “You are the only one who can control your happiness,” Hasey said. “And that’s what I do.” Credit: Kit Wiberg for Block Club Chicago

“We want to make sure that we get the same exact setup for each station that they go to. So if you go to the glass station, you’ll see they have the same amount of stickers on each side. And each of the panels for the graffiti is sprayed the exact same way,” said rail station manager Jason Porter.

Porter was one of the judges overseeing the track meet-like competition, timing employees and scoring them on their ability to follow proper protocol. He also occasionally tossed oatmeal, ketchup and other food items on the floor during another competition simulating biohazards CTA employees can encounter in the field. 

Each time an employee completed the biohazard station, Porter carefully reset the challenge in the same Jackson Pollock-esque pattern of foodstuffs for the next competitor. 

“We do the exact same pattern with that stuff because we don’t want to give anybody an unfair advantage,” Porter said. “We make sure everything is the same, everything is equitable so everybody can compete on the same level.”

Employees were also presented with a variety of cleaning tools and personal protective equipment to select before entering the competition arena. 

“Our more seasoned employees, they’ll choose to use a different tool versus some of our newer employees, who haven’t quite yet mastered how to use them,” said Stacy Hill, a CTA employee helping oversee the janitorial competition. 

Veterans can remove a stubborn sticker in one decisive motion, she said. 

“I’ve actually seen employees — literally with one tug of the end with the scraper — just pull it off in less than five seconds,” Hill said. “You see some interesting stuff.”

Twania Waddell works on scrubbing a surface of chemicals and paint on Saturday, Sept. 13, 2025, in Skokie. Workers were timed on the challenges and scored on a variety of different aspects. Credit: Kit Wiberg/Block Club Chicago Steve Mascheri falls into the dunk tank after the target was hit on Saturday, Sept. 13, 2025, in Skokie. After the rain cleared, festivities were able to continue outside including rides on mini trains, games and more competitions. Credit: Kit Wiberg/Block Club Chicago

Miguel Davila — who is on the janitorial staff at the Blue Line’s Grand station, 502 N. Milwaukee Ave. — is a legend among the CTA’s cleaning crews as one of the top contenders in the Jamboree competition for eight years. 

Before tackling the biohazard challenge, Davila quietly assessed the mess. Once the judge holding the stopwatch gave him the go-ahead, he was a blur of mops, brooms and cleaning solutions. 

“My mentality? I don’t do anything unless I’m gonna win,” Davila said. “I kind of fight with myself, that I could be better than what I’m showing everybody. I know I could do better. I beat myself up.”

Davila first competed in the Jamboree 20 years ago and said he wasn’t as good as he is now. The annual event has allowed him to learn from veterans, refine his skills and pass those techniques to the CTA’s younger janitorial staff, he said. 

“If people ask me what do I think about this? I give them advice, yes. I don’t keep it to myself,” he said. “I’m not being greedy. I want them to do good, too.” 

Attendees of the CTA Jamboree walk through a vintage train on Saturday, Sept. 13, 2025, in Skokie. The train was built in 1923 by Cincinnati Car Co. and was retired in 1973. Credit: Kit Wiberg for Block Club Chicago Marz Phipps, 6, throws a bean bag to knock down wooden characters during the CTA Jamboree on Saturday, Sept. 13, 2025, in Skokie. The festivities had to move indoors due to the rain for most of the day. Credit: Kit Wiberg for Block Club Chicago

The transit agency has hosted the event since the 1980s. Sunday’s stormy start to this year’s Jamboree also gave friends and family of CTA employees a glimpse into how they keep things rolling for millions of Chicagoans, rain or shine. 

As thunder cracked and lightning flashed, CTA employees quickly pivoted much of the event’s activities indoors until the sun returned. During the storm, staff like Max Winkelstein, a CTA carpenter, used large brooms and squeegees to push rainwater out of the massive industrial building’s large, half-open service doors. 

“We live in the Midwest. In Chicago. We’re always going to encounter crazy weather. You just shrug it off, you know?” Winkelstein said.

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September 19, 2025 at 10:50AM