South Cook News

As anti-Trump demonstrations swept across Illinois over the weekend, a parallel show of force emerged in the Chicago suburbs, where supporters of President Donald Trump gathered for what organizers called a “Trump Birthday–Flag Day Overpass Parade.” 

The event, hosted by the grassroots group Trump Illinois MAGA Official (TIMO), took place Saturday evening on the Willow Springs Road overpass above I-55 and drew several hundred participants, according to group member David Dewar.

“We had about 300 people on the bridge,” Dewar told South Cook News. “We celebrated Trump's 79th birthday, Flag Day, and the 250th year of the U.S. Army. It was an incredible celebration.”

David Dewar and another Trump supporter stand with cars zipping by on I-55 in the background. | Facebook / David Dewar

The June 14 event featured flag waving, a decorated vehicle parade, a barbecue and a birthday cake ceremony at dusk. 

Organizers encouraged attendees to bring their Trump gear, lights and posters. The patriotic display prompted frequent honks of support from truckers on I-294 and drivers on nearby 104th Street.

“It was unbelievable,” said Dewar. “We had flags, we waved them as people passed, food, and then a big birthday cake celebration. Channel 7 came out. They interviewed me and some others.”

According to Dewar, TIMO is quickly gaining visibility and momentum in the Chicago area, with potential political ambitions in sight. 

Looking ahead, Dewar, who is known in the Chicago suburbs for his frequent appearances as Uncle Sam, suggested that TIMO could evolve beyond rallies and protests, hinting at potential political ambitions tied to the group’s growing grassroots momentum. 

“This group, it looks like we’re strategizing, but we may be running candidates off of this group,” Dewar said. 

The Countryside gathering took place on the same day as nationwide “No Kings” protests, including several in Illinois, which painted Trump as an authoritarian threat to democracy. 

Conservative commentator Christopher Rufo dismissed the protests as political theater. 

Rufo argued that the demonstrations were “rooted in fantasy” and failed to reflect the constitutional limits Trump operates under. 

“The only way to stop him is to flood the streets and persuade the American people that Trump is a rotten character with despotic ambitions,” Rufo wrote. “The theory, of course, is nonsense. Trump is a duly elected president. He is working with Congress on the budget. His deportation policy, which lent momentum to the weekend’s demonstrations, is predicated on enforcing existing law.” 

Those protests followed a June 10 anti-ICE riot in Chicago, where demonstrators vandalized police vehicles and federal buildings, defaced a Tesla with swastikas, and assaulted law enforcement officers. 

Seventeen people were arrested in the aftermath.

For Dewar and other TIMO members, the contrast between the escalating unrest on the left and the celebratory tone of Saturday's overpass event reflects deeper political division in the state. 

“There’s just too much confusion within the Illinois Republican Party,” Dewar said. 

Frustrated with what he sees as disorganization within the state’s Republican leadership, Dewar emphasized his preference for the clarity and shared purpose he finds in TIMO. 

“At least I know with this organization who I’m dealing with,” Dewar said. “We’re all more about the cause, as opposed to an agenda or climbing the totem pole.”

Saturday’s rally marks one of several public demonstrations by TIMO this year.

In April, the group organized a protest outside a Holiday Inn near Midway Airport, drawing attention to Gov. J.B. Pritzker’s use of taxpayer funds to house undocumented migrants.

The site was one of several for which Pritzker’s administration allocated $638 million in taxpayer funds toward Chicago’s migrant crisis, including a $160 million plan aimed at shelter and job assistance.

That event drew about 20 participants and was similarly marked by Trump flags and anti- illegal immigration slogans. 

TIMO leaders say more events, and possibly political campaigns, are on the horizon. 

“These particular individuals are really patriots,” Dewar said.  

Dewar described the group’s growing support base as distinct from traditional party structures, emphasizing its strong alignment with Trump’s movement.

“The type of people we get are Trump MAGA people,” he said. “We don't necessarily get establishment or Republican, Illinois Republicans. So I would say, realistically, we're getting people from all those areas—Cook, DuPage. Well, we have a good base from the last one. And they're Trump people, that's it.”

Dewar himself ran as a “JFK-style Democrat” for the Illinois House of Representatives in District 35 but was defeated in the March 19, 2024 Democratic primary by incumbent State Rep. Mary Gill (D-Chicago), receiving 15.6% of the vote.  

Speaking about the dedication and motivation of the group’s members, Dewar highlighted their genuine commitment beyond traditional party politics.

“They're really faithful, and they're truly grassroots people,” Dewar said. “There are people, there are comments, that are really concerned about the country, the state, and the cause—not about political party agendas. So that's why we're getting big numbers. You know, people are sick of the bull crap, and they know when they're being bamboozled by their party.”

Images from the Willow Springs Road overpass pro-Trump event in Countryside. (Facebook / David Dewar)