Chicago Flips Red
A small group of counter-demonstrators turned out for this year’s International May Day rally in Union Park. I recall hearing references to “Chicago Flips Red” as I photographed that group interacting with the people who had come to march in support of workers’ rights. I thought, “What’s that all about?” Today at noon, I found out. Chicago Flips Red (“CFR”) held a rally in Daley Plaza. I don’t know whether it is a political party, but it bears some resemblance to one.
Given the lackluster attendance, CFR’s movement appears to be in its infancy. According to the group’s website,
We're not politicians. We’re everyday Chicagoans who got fed up with one-party rule, broken promises, and the silencing of anyone who dares speak up. Chicago Flips Red is a grassroots movement built on showing up, speaking out, and demanding better.
To date, CFR has raised over $20,000 and has recruited over 200 volunteers.
The group currently supports a number of candidates for public office. With one exception, all are identified as Republicans on the group’s website. Among CFR’s candidates are Christian Maxwell, who is running for U.S. Congress in the First District, and Danielle Carter-Walters, who is running for Mayor of Chicago. Carter-Walters was today’s principal speaker.
To pump up the six or seven people who turned out, CFR relied on DJ Dink to bring musical energy to the occasion. To be blunt, Carter-Walters and the two women who stood with her don’t have a clue about how to stage a rally. Rule 1: Don’t give a speech with loud music playing during the entire speech. Rule 2: Don’t have two people walking back and forth across an otherwise empty stage while you speak; it’s a distraction. Rule 3: Practice your speech. I couldn’t tell whether Carter-Walters was giving an impromptu address or whether she was just poorly prepared. While she is a charismatic speaker, her verbiage was jumbled at times.
To her credit, Carter-Walters focused on kitchen-table issues, including building generational wealth, crime, and high property taxes. While those issues affect everyone across the political spectrum, Carter-Walters was addressing them through the lens of the Black community residing on Chicago’s South Side. She recounted how she and her husband, a retired Chicago Police Department officer, lost a building that they owned to what I assume was a forced sale for unpaid property taxes.
Carter-Walters called out Chicago Teacher Union president Stacy Davis Gates, claiming that Gates’ son attends a private school and that Gates owns property in Indiana. Later in her remarks, Carter-Walters turned her spotlight toward Indiana, pointedly asking why people cross the Illinois-Indiana border to buy gasoline, groceries, and property in Indiana. Carter-Walters noted that this movement is from a Blue state to a Red one. Yet, to Carter-Walter’s consternation, the people crossing into Indiana continue to vote for Illinois Democrats.
Carter-Walters is particularly troubled by what she terms “illegal aliens,” as well as the homeless camped on street corners. As for the “illegal aliens,” Carter-Walters views them as replacements for hard working Chicagoans. Although Carter-Walters made only one or two references to Donald J. Trump, her pitch to the working-class Blacks on the Chicago’s South Side was all MAGA. If I heard her correctly, she claimed that Governor Pritzker has the State of Illinois paying the rent for “illegal” aliens” so that they can hide from ICE. That claim is about as Trumpy as it gets.
Carter-Walters is also concerned with Chicago’s failing public school system, citing abysmal reading and math proficiency scores. She is calling for School Choice as an antidote.
During her highly charged remarks, Carter-Walters also called out Mayor Brandon Johnson’s security detail. According to her, the mayor’s security detail includes 150 police officers at a cost of $30 million per year. Yet, according to Carter-Walters, everyday Chicagoans experience mass shootings every day, meaning everyone but the mayor goes unprotected.
Carter-Walters also objected that Illinois does not require voter ID, which clearly tracks Trump’s position.
No fan of Governor Pritzker, Carter -Walters also attacked Lieutenant Governor Julia Stratton, who is running for U.S. Senate. Carter said Stratton was a “No” vote for the Senate seat being vacated by Senator Richard J. Durbin.
At several points in her remarks, Carter-Walters made reference to the proliferation of kidney dialysis centers on Chicago’s South Side. She takes this proliferation to be a sign of poor diets, which are a consequence of so-called food deserts.
She pointedly asked, “When is enough is enough?” She then asked why people are not protesting “mass genocide” in our communities.
Toward the end of her remarks, Carter-Walters returned to Trump and Pritzker, noting that Trump is trying to cut gasoline taxes, while Pritzker has increased energy and gas taxes by 25%. In further comparing the two, Carter-Walters claimed that Trump tried to keep the country open during the Covid pandemic, but Pritzker shut Illinois down.
Toward the end of her remarks, she noted that Morton Salt had left Illinois for Overland Park, Kansas yesterday and that Walgreens has also left. In the case of Walgreens, she must have been referring to store closures rather than the corporate headquarters because Walgreens’ corporate headquarters remains in Deerfield, Illinois.
In concluding, Carter-Walters noted that “you vote Blue,” but that people leave Illinois when they retire, heading to Red states like Florida, Georgia, and Texas. Following Carter-Walters’ remarks, a woman who was introduced as Pastor Sandy took the podium, offering a closing prayer.
Throughout her speech, the CBS jumbotron across from Daley Plaza flashed reports of shootings and a smash-and grab. At one point, Carter-Walters looked at the screen, noting the report of a smash-and-grab.
While the rally was a total bust from the standpoint of attendance, Mayor Johnson, the Chicago City Council, and state officials should not be too quick in dismissing Carter-Walters as an outlier. She strikes me as someone who is connected with her community. I think she is best viewed as an early-warning sign that those living on the South and West sides of Chicago in predominantly Black communities are dissatisfied with the Democratic agenda, or at least believe that it is not satisfying their needs.
[Click on an Image to Enlarge It. The Images Are Not Necessarily in Exact Chronological Order]
A Sign of the Violence that Danielle Carter-Walters Is Speaking About
Not the Crowd that The Organizers Had Hoped For
DJ Dink Spinning the Beats
Zoe Leigh Speaking with a Bystander
Mayoral Candidate Danielle Carter-Walters Making Her Point
Too Many Distractions
Another Example of the Crime that Concerns Mayoral Candidate Danielle Carter-Walters
Pointing Toward Mayor Brandon Johnson's Fifth Floor City Hall Office
Offering Encouragement and Maybe a Suggestion, While Jessica Jackson Looks On
Carter-Walters Referenced This Smash-and-Grab During Her Remarks
Too Much Movement on the Stage as Carter-Walters Speaks
Angry About High Property Tax Levies
Carter-Walters Standing Next to Pastor Sandy
Joined Together in Prayer
All Smiles
Copyright 2026, Jack B. Siegel, All Rights Reserved. Do Not Alter, Copy, Display, Distribute, Download, Duplicate, or Reproduce Without the Prior Written Consent of the Copyright Holder.



