Members of Chicago Flips Red (Photo Courtesy of Chicago Flips Red).
Chicago Flips Red aims to turn Illinois into a red state, push out corrupt officials and hold leaders accountable.
The organization demonstrates that even within the solidly “blue wall” of Illinois, where Donald Trump lost by 11 percentage points to Kamala Harris, and in Black Chicago, there exists a faction of dissatisfied Black voters who would instead identify as “red” and look forward to these next four years with Trump as President.
They believe that Trump’s presidency could spur progress, restore the city’s integrity and benefit Black people.
“People are reaching out to us, wanting to take this movement nationwide,” said Jessica Jackson, a Chicago Flips Red activist. “It made sense at one point for Black Americans to support Democrats, but times have changed, and we need to understand what each party stands for in terms of economic survival.”
Like counties in other states that have successfully flipped, fought for resources, and secured their rights, CFR is committed to fighting for African Americans who aspire to stability and to keep what they deserve. The organization also wants to spark conversations about critical topics in the Black community, like financial literacy, knowledge of the law and political empowerment.
Core members Jackson, Patrice Stewart, Zoe Leigh, Danielle Carter, David Mason and others have united over personal injustices they say they’ve incurred from the city government and the challenges posed by what they see as illegal immigration in Chicago.
Disheartened by the current Democratic leadership, they aim to reform the political system to ensure fair representation for all, with a particular focus on the African-American community.
How They Flipped Red
Photo Courtesy of Chicago Flips Red
Each CFR member became invested in their mission and ideology through loss, injustice, frustration and disillusionment with local government.
Stewart, a tax and business strategist, shared about her mother’s encounter with the migrants that moved into her community and caused disturbances.
“My mother lived in Woodlawn in a senior facility; she’d been frustrated with the illegal immigrants behind her building. It became an inconvenience for what the city allowed.”
Stewart added, “One day, a Venezuelan man even pushed an 85-year-old woman, which led to the whole neighborhood confronting them.”
“Things got so bad that one of them pooped in broad daylight in front of the building, showing utter disrespect for the seniors,” she said. “This experience made me realize how the system fails us. Coming from a family of civil rights fighters, I knew I couldn’t stay silent.”
Jackson shared that she became involved after experiencing “property theft” during the probate process following her mother’s death.
“I first became aware of how Black people’s property was stolen through the probate process after my mother’s death,” she said.
It went viral when she spoke out at City Hall about her ordeal. Chicago Flips Red grew out of her frustration with the city’s political structure.
“Everything was dominated by Democrats—the judges, the public administrators, and all the city commissioners,” said Jackson. “As I navigated the corrupt court system, I realized there was no place to turn for help because the system was all controlled by Democrats. That’s when I felt compelled to speak up, especially for myself and Black people.”
What brought Leigh to the movement was a similar circumstance to Jackson’s.
“I came here from Atlanta to fight for my mother’s property after it was unlawfully demolished through illegal eminent domain,” she claims. “When they refused to settle her case, I decided to get involved because I believe in the U.S. Constitution and that it should be upheld.”
Leigh added, “I went to City Hall, believing they would respect the Constitution, but for the court system to deny her due process and the protections guaranteed by the Constitution felt like a betrayal.”
She sought help at the federal, state and local levels, but to no avail.
“When nothing changed, I remembered what happened in Georgia in 2020. So, I decided to flip this city red and stayed committed to the cause.”
Carter, a fitness trainer and business owner, encountered numerous obstacles after she bought a building in her neighborhood in 2019.
“I encountered constant barriers—denied loans, lack of support for Black-owned businesses, and resources being directed elsewhere,” she said.
Carter added, “Despite being in an opportunity zone and paying high taxes, I could not secure funding, while Mexican businesses flourished, receiving the resources I couldn’t access.”
“Immigrants set up unregulated street restaurants, which further fueled my frustration. It became clear that change was needed,” she said.
Why They Flipped Red
Jessica Jackson of Chicago Flips Red (Photo Courtesy of Chicago Flips Red).
At a Trump rally in Wisconsin, Jackson was struck by his comment, “The problem in our country today is we have too many people in positions who don’t love America.”
She noticed a strong sense of unity and patriotism at Republican rallies, where people are viewed as Americans first.
Echoing her sentiment, Leigh said, “I realized this is why our communities have remained the way they are—because we have no real leadership. There’s no strong Black leadership. They always play the race card, but that’s not the issue. The real problem is that we have gatekeepers in place.”
Leigh places the blame squarely on the predominant party in the city.
“The Democratic Party profits off our oppression, and that’s all it is. They don’t want us to own businesses, to have property, or to build generational wealth. And these are our people doing this to us. Seeing all this made me angry and deeply disappointed,” she said.
As the team focuses on the challenges facing the African American community, expressing frustration with the lack of support from government leaders, CFR points out that resources are being prioritized to other cultures and illegal immigrants only. In contrast, American citizens, particularly Black people, are left to struggle.
“We know there are immigrants here from different countries, but there are Black people and legal people who live here, pay taxes, and work hard and can’t get the same treatment. Meanwhile, newcomers who’ve never voted or paid taxes get VIP benefits like housing, food and cash assistance instantly,” said Stewart.
About Trump and The Republican Party
Being aligned with Chicago Flips Red doesn’t necessarily mean that members are Republican, but they see Trump’s re-election as a fortuitous development.
“I don’t align with any party, but I believe financial literacy and community empowerment are key to breaking free from political machines and building a better future,” said Stewart.
Jackson expressed that Trump is the leader of this country “who understands the injustices of the courts because he’s going through it too.”
“Trump’s presidency will bring opportunities for change. We can’t make the same mistake with Republicans that we made with Democrats,” Jackson said.
“We need to fight for four key areas—property, education, justice, and jobs—and this will bring more Black Americans to the Republican Party.”
For Carter, it isn’t so much about who is president as the values that each political party stands for.
She said that the media distorts narratives about political leaders, pointing out that if the press provided honest coverage, people would see the truth about them.
Chicago Flips Red believes that Trump’s second presidency could transform national and local politics, with an increasing number of Black Americans realizing the importance of political engagement at the local level.
What They Want
Zoe Leigh and Jessica Jackson (Photo Courtesy of Chicago Flips Red).
For its members, the motivation to continue the Chicago Flips Red movement is progress:
“We’re talking to people in cities where Black people have been losing for years,” said Jackson.
They also want more Black people to engage in local government, namely City Council meetings.
Stewart added, “At a recent City Hall meeting, I was stunned to see aldermen speaking in Spanish without any interpretation for English-speaking citizens. This violates our rights and shows how other communities can have their way while we’re left in the dark; it’s time for us to show up, speak up, and demand better treatment from our government officials.”
Acknowledging the challenges ahead, CFR stresses the need to stay focused on its mission, understanding that not everyone will agree. For the organization, it’s about showing up consistently, taking action and ensuring the voices of its members are heard as the fight extends beyond individual interests. Ultimately, it’s about creating a better future for the Black community in Chicago.
“If you want to see for yourself what we’re talking about, come down to City Hall,” Stewart said.
“As Black people, we need to unify and show up at City Hall and other levels of government; we can demand change. We can’t stay silent while others fight for what they want.”
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