The women in red hats are met with eye rolls, indifference and jeers during Chicago City Council meetings.
But in the past week, their movement has been embraced on live TV inside the Oval Office.
“I see Black women wearing a red MAGA hat last night on television: ‘Please let the president come in,’” President Donald Trump told reporters on Tuesday from the White House. “You have a force of Black women, Black women … they want Trump to come in. And you see them, they’re all over the place in Chicago.”
The broadcast followed Trump’s explosive remarks Friday floating the nation’s third-largest city as “probably” the next destination to send military troops in his purported crusade against violence. That day, he first cited “African American ladies, beautiful ladies” begging him for federal intervention in Chicago as he answered questions about the ongoing, controversial deployment of 2,000 National Guard members in Washington, D.C.
The president’s comments triggered a seismic rebuke from Democrats who scoffed at the notion he spoke for Black women in America, much less Chicago.
Some local observers of City Hall’s quirks and characters knew exactly who he was talking about.
For over two years, a small but vocal group of Black Trump supporters has occupied a corner of the public seating in Council Chambers, testifying at virtually every meeting to excoriate Mayor Brandon Johnson and other Democrats.
Sporting red shirts and hats with variations of the “Make America Great Again” slogan, the dozen or so Trump supporters have delivered impassioned and indignation-heavy tirades accusing Johnson of betraying the Black community, sometimes as the council sergeant-at-arms dragged them out shouting for breaking decorum rules.
One of them, Patricia Easley, credits Trump’s supposed discovery of her conservative activism to the democratization of the internet.
“I’ve been in this realm for a while, but I’m glad that the barriers that existed before when it comes to addressing people in power no longer exist,” Easley said. “If you tell people, ‘I’m going to make this video, make it go viral, I want to make sure that blah blah blah sees it,’ the algorithm works to help you accomplish that.”
Patricia Easley, left, gives a thumbs down as she reacts to Mayor Brandon Johnson’s budget address during a City Council meeting on Oct. 30, 2024, in Chicago. Jessica Jackson, of Chicago Flips Red, is on the right. (Stacey Wescott/Chicago Tribune)
The women have much to gain. Their liberal critics say a rich benefactor must be bankrolling their movement — a charge they staunchly reject.
Some of the Trump supporters say they are driven by unresolved gripes against Chicago government. Others livestream their City Council criticism and post to social media, where they solicit donations and sell merchandise. Easley recently launched a bid for Congress, running as a Republican for the seat U.S. Rep. Danny Davis plans to vacate.
And all claim they want to upend the city’s one-party rule.
Ameshia Cross, a Democratic strategist who grew up in South Shore, stressed that Black women in Chicago strongly oppose the president. Still, she noted how Trump’s public endorsement of the city’s MAGA minority reflects how attention-grabbing antics have become currency in today’s internet-fueled politics.
“The Black ‘MAGA’ Republicanism in general has largely been driven by a set of grifters,” the South Shore native said. “In many cases, it is notoriety, getting on television, being able to write a book, being able to appear on podcasts. … If you say enough, Trump will elevate you, he will tweet you, he will talk about you from the White House, he will invite you in. And these are individuals who crave that level of attention.”
Despite the local disdain, several women have rushed to claim the mantle of Trump’s “beautiful” African American ladies.
But instead of a glass slipper, they are pulling out a digital arsenal to prove they are the mystery women.
Patricia Easley, the 37-year-old West Sider who started the group ChicagoRED, Aug. 26, 2025. (Antonio Perez/Chicago Tribune)
Easley, a 37-year-old West Sider who started the group ChicagoRED, can quickly dig up a shout-out to her from the president’s Truth Social, an autographed photo to argue her case and a text she claims is from a White House liaison: “The African American he was talking about was you btw.”
A separate faction of Black Trump supporters in Chicago, Chicago Flips Red, also had a repository of personalized notes from the White House and photos of their City Council appearances emblazoned with Trump’s signature.
“Oh, we knew he was talking about us,” member Danielle Carter, 50, said. “He sent us love notes. … Our president is listening to us. We kept saying that because he’s the people’s president.”
Regardless of which women Trump was talking about, they say their respective skyrocketing profiles reflect a new playbook in American politics that’s allowed a fringe coalition in liberal Chicago to find a direct line into the White House.
Easley said her interview last year with former Fox News anchor Pete Hegseth, now the U.S. Defense Secretary, prompted Trump to post in April 2024: “‘P RAE’ EASLEY – I watched your great interview tonight … We will put Chicago into the winning mix! Will be calling you. Love to all, DONALD J. TRUMP.”
The next month Easley accepted an invitation to Trump’s Waukesha, Wisconsin, rally, where the two posed in a “prom photo” as the GOP candidate gushed that she was “so beautiful” and he was “watching your work.”
The White House did not respond to inquiries about Trump’s remarks or his relationship with conservative Black Chicagoans.
Illinois Democrats have noted that the cable TV strategy works on the president as well. On Monday, Gov. JB Pritzker told reporters, “I know (Trump) doesn’t read … but I know he watches television. And so perhaps if somebody from Fox News or from Newsmax is here, they’ll cover” Chicago’s drop in crime.
Zoe Leigh, Chicago Flips Red cofounder, holds her phone showing an email sent to her from the office of President Trump. (Eileen T. Meslar/Chicago Tribune)
Danielle Carter, center, of the pro-Trump group Chicago Flips Red, argues with people protesting against U.S. Immigration and Customs Enforcement raids at Federal Plaza in Chicago on June 10, 2025. (Terrence Antonio James/Chicago Tribune)
The governor said Wednesday he had no further clarity on whether the president planned to follow through on sending troops to Chicago.
“You know, at this point, so much of it is rumor,” Pritzker told reporters. “Even things that we’re hearing through our office, people calling who are not calling in their official capacity to let us know what’s going on. We only know so much. Right now, it’s hard to tell. We haven’t seen troop movements yet. We also haven’t seen any call-up of our National Guard.”
Local leaders such as Johnson have cited statistics showing shootings in Chicago are down 36% and homicides 31% so far this year in arguing that a military occupation is unnecessary, as well as illegal.
There’s a Chicago precedent for cable news appearances preceding Trump action.
Another former Democratic Illinois governor, Rod Blagojevich, saw his prison sentence commuted by Trump after his wife, Patti, made the rounds on Fox News flattering the president during his first term. Trump gave Blagojevich a full pardon this year.
To be sure, Chicago is more likely to see another Super Bowl Lombardi Trophy than to flip red. A Republican has not won citywide in a century, and Trump resoundingly lost the vote in the past three elections.
However, his share of the vote did grow in Chicago and other big cities last November, largely because of a drop-off in support for the Democratic nominee, Kamala Harris, compared with Joe Biden in his 2020 defeat of Trump. Ultimately Trump netted 20.3% of the vote in 2024, versus 15.8% in 2020 and 12.4% in 2016.
Last election’s results suggested not so much a rightward swing as voters on the South and West sides simply staying home, pointing to signs of disaffection over Democratic leadership.
Zoe Leigh, right, Chicago Flips Red cofounder, answers a question during an interview while Danielle Carter, vice president of Chicago Flips Red, sits nearby at their office in Hyde Park on Aug. 26, 2025. (Eileen T. Meslar/Chicago Tribune)
While that apathy is a far cry from their steadfast embrace of Trump, the red hat groups’ steady drumbeat of often deeply personal insults targeting Johnson’s standing among Black Chicagoans is an attempt to get under the mayor’s skin and catch attention from outside City Hall.
Johnson won election in 2023 with a coalition of Black voters and white liberals, but his brand of leftist politics has struggled with that first base after a sudden crisis of asylum-seekers landed on his desk his first day in office. And he has become a regular target for Trump, allies say, because of his identity as a Black progressive.
For his part, Johnson has maintained his cool throughout episodes on the council floor where Black Trump supporters have insinuated he is a race traitor and should be in prison. Asked Tuesday about Trump’s reference to the women, Johnson avoided mentioning them.
“I’m paying attention to the things that are actually working,” he said.
The office of Chicago Flips Red is tucked inside the second floor of a co-working space in the Hyde Park neighborhood. A ring light and iPhone stand are set up at all times on Carter’s desk.
When her cofounder Zoe Leigh, 39, rants about the injustice she’s faced under local Democratic leadership, her rhetoric at times resembles that of Johnson and others within Chicago’s progressive movement — until she touches upon immigrants.
“They have taken everything out of our communities, I mean literally down to the slides, to the swings, to the basketball courts,” Leigh, a Bronzeville resident, said. “We have dealt with mass incarceration. We dealt with the crack epidemic. We dealt with COVID. We dealt with this illegal immigration that just came over here. We keep getting pushed out.”
Leigh, who said she is lesbian, said she never cared for either political party until she faced hurdle after hurdle while fighting the demolition of her mother Charlene Marsh’s building in the Gresham neighborhood. Marsh’s years of litigation against the city have been unsuccessful so far.
Leigh was arrested during a 2023 City Council meeting for causing a disturbance and refusing to leave, according to a police report. She pleaded guilty to disorderly conduct and was given a year of supervision.
Zoe Leigh, center, of Chicago Flips Red, records video and shouts at dozens of pro-drag activists blocking and protecting arriving attendees to a drag story hour at the Beverly branch of the Chicago Public Library on June, 3, 2025. Several Chicago Flips Red members shouted anti-drag messages. (Antonio Perez/Chicago Tribune)
Carter, meanwhile, said she broke from the Democrats after her husband was forced to get the COVID-19 vaccine to keep his job as a Chicago police officer.
Following Trump’s comments, Ald. Jeanette Taylor, 20th Ward, offered a brief description of the women the president cited: “nuts.”
The Woodlawn alderman, who is Black, said some City Council MAGA commenters such as Leigh were genuinely wronged by Chicago government, but conservative leaders are using them as “loud and wrong” pawns to inflame racial tensions.
“They’re just using people who look like us to steer a narrative that we all know is not true,” she said. “Some Black people need to shut their … mouth and do better with helping their community and mentoring young people.”
The ChicagoRED political action committee Easley established last year has not reported any donations. Easley, who state business records show launched a political consultancy in March, said she has only gotten small donations. Leigh registered Chicago Flips Red as a business in February.
Back at her Hyde Park office, Leigh concedes she’s unlikely to win over City Hall anytime soon. But she has grander sights, she maintained while waving a Trump-autographed photo of her ripping into the mayor during a council meeting.
“People used to laugh,” Leigh said. “I don’t think they laughing anymore.”
Tribune reporter Jeremy Gorner contributed.
Originally Published: August 27, 2025 at 3:27 PM CDT