CHA Operating Chair Matthew Brewer, who is embroiled in a power struggle with Mayor Brandon Johnson, is seriously considering entering the race for mayor.
Three prominent business leaders who asked to remain anonymous said Brewer has been meeting with influential members of Chicago’s business community for weeks in an attempt to sell himself as a difference-maker with a compelling personal story.
That includes both one-on-one meetings and appearances before the board of “One Future Illinois.”
The non-profit group with an affiliated political action committee was created two years ago to advance their “long-term, systemic civic priorities for the city and state.” After defeating Johnson’s “Bring Chicago Home” referendum and blocking the mayor’s proposed corporate head tax, the group is screening candidates for mayor in an attempt to unite behind a challenger.
Brewer refused to discuss his interest in entering the race for mayor, now just nine months away. Mayoral candidates can begin circulating nominating petitions in late July. Those petitions must be filed by Oct. 26.
“He’s a lifelong Chicagoan who is not happy with the situation. He thinks he has the background and skills” to take the city in a different direction, said one business leader who heard Brewer’s sales pitch. “There are a lot of people looking at this and trying to figure out if there’s a lane for them and if they could win. Some of them will actually proceed. We’ll see what he puts forward as his vision. He would bring a lot of intensity and energy to the race.”
Another business leader who has met privately with Brewer said the CHA board chair’s pitch, at least so far, begins and ends with his rags-to-riches story.
A father who battled drug addiction. A mother who took her two young children away from that situation and raised Matthew and his brother in poverty on her own. Brewer went on to become the first student of color to serve as student body president at Stanford, then earned an MBA at Harvard and a law degree at Yale simultaneously.
He is a partner at Bartlit Beck, a prominent Chicago law firm. He also owns a marijuana dispensary with his mom and brother.
Sources said Brewer’s recent appearance before the One Future Illinois board was impressive. But what it lacked is a detailed explanation for why he is running, and what he would do if he wins the 2027 race for mayor.
If Brewer puts that missing piece in place and raises enough money to introduce himself to Chicago voters, he could be a difference-maker, according to veteran political operative and Cook County Commissioner Michael Scott Jr.
Johnson has not yet declared his intention to seek a second term. His public approval rating is still languishing in the low 30s and he has just $813,125 in campaign cash on hand — compared to $18.3 million for Illinois Secretary of State Alexi Giannoulias.
But the embattled mayor still has the far left lane to himself and is the only prominent African-American considering the race.
Brewer’s entry into the already-crowded race could alter that equation, Scott said.
“We’ve elected two African-American mayors because of the Black vote in Chicago in the last two cycles. So this could cause a problem for Johnson. But it could hurt Alexi as well,” said Scott, a former alderperson whose sister replaced him the City Council.
“Brewer is a smart, educated, well-spoken African-American with ties to the business community, [and] now in the public sector. He tells a compelling story. … He could catch fire the same way that Johnson did with a little bit of money, a little bit of name recognition a little bit of a plan to move the city in a different direction.”
The longer Giannoulias waits to enter the race, the greater the chance that Brewer could catch fire, Scott said.
“Because of the money that he’s amassed, Alexi has an excellent chance of putting a good story out and making sure that his story is told the way that he wants to. But he has not gotten to the starting line yet,” Scott said. “The longer you wait in this election cycle, the more people jump in. It allows for another candidate to take the business community, to take the progressive community, folks who are looking for a candidate to jump on that horse.”
Brewer’s flirtation with mayoral politics comes at a pivotal time for the public housing agency he leads.
For more than 16 months, the public housing agency limped along without permanent leadership as Johnson tried and failed to install retired City Council dean and Zoning Committee Chair Walter Burnett Jr. (27th) as the CHA’s CEO.
The U.S. Department of Housing and Urban Development blocked the move by refusing to grant Burnett the waivers he needed to resolve conflicts of interest.
Tensions between the mayor and Brewer began to rise once the CHA board passed a resolution at an October 2025 board meeting for Brewer to continue serving as operating chairman and to forge ahead with the selection of a new CEO. At the time, Brewer described the resolution as “a statement” to show the public that the board was proceeding with the CEO selection process.
The tensions between Johnson and Brewer hit a boiling point when Johnson said in April that he had removed Brewer from his role as board chair and interim operating chairman. Brewer said he wasn’t going anywhere.
It remains unclear if the mayor followed the proper procedures to do so. Brewer argues the mayor hasn’t.
Johnson’s move followed the CHA board’s 7-2 vote in March to approve the appointment of Keith Pettigrew as the agency’s new CEO for a four-year term. The vote marked a win for the board over Johnson, who had not given up his push for the appointment of Burnett.
The mayor and his leadership team have argued that the vote to install Pettigrew was illegal because it violated the Open Meetings Act and the required public notice. Johnson’s allies have filed a still-pending lawsuit challenging the vote to install Pettigrew on those grounds.
The CHA supports 65,000 households, is the biggest owner of rental housing in Chicago and operates with a yearly budget of $1.4 billion.