Mailers for school board race go negative — from Project 2025 to attacks on the mayor

In recent weeks, a new kind of mailer has been piling up on doorsteps across the city  — ads for and against candidates for the soon-to-be-elected school board.

With 31 candidates and money pouring in from the Chicago Teachers Union and charter-aligned groups for 10 hotly contested seats, these ads look a little different, with cut-out portraits of unsmiling contenders and menacing messages. Like the kinds of mailers seen in legislative and aldermanic races, they are sometimes darkly political and stick to straight politics, even though some of the country’s most polarizing education issues — officers in schools, book-banning and critical race theory — aren’t discussed.

What is being discussed…on mailers for a school board election: Donald Trump’s agenda should he be elected on Nov. 5.

“If Trump Republicans and out-of-state billionaires get their candidate — Ellen Rosenfeld — elected,” reads one pamphlet paid for by a CTU Local 1 Political Action Committee. Then, in smaller lettering: “Donald Trump’s 2025 agenda will crush our public schools.”

Charter proponents and CTU have been longtime enemies and now their Board of Education fights are spilling into people’s living rooms in the form of these mailers. As all of them are likely Democrats, the labels paint a bizarre picture of the people running for school board seats.

With the future power of Chicago education in the balance and CTU-backed Mayor Brandon Johnson on the 5th floor of City Hall, both sides are doing whatever they can to win the races at stake.

Charter-affiliated interest groups have spent close to $500,000 on mailers alone since late September — not counting other forms of advertisement — through their super PACs, according to state election data. CTU and its affiliated groups have been spending similar amounts in the race and have put out mailers of their own.

And while Trump-aligned campaign strategies may seem bold to some targeted candidates, groups aligned with charter schools are also taking the most extreme versions of policies by democratic office-holders and applying them to their advertising battles.

In the 2nd District, for example, one mailer opposing CTU-backed Ebony DeBerry’s bid — paid for by Illinois Network of Charter Schools’ super PAC — features a picture of Mayor Johnson and reads “Mayor Johnson’s political agenda is causing chaos in our public schools.”

The ad notes the recent resignation of Chicago’s school board, which took place amid Johnson’s campaign to oust Chicago Public Schools CEO Pedro Martinez, a stunning shake-up as CTU is negotiating a demanding new teachers’ contract and the union-backed mayor has pushed for the district to take out a high-interest loan to cover its costs. The fate of the district’s CEO has been top of mind when it comes to what influence the new school board will have on education in the city.

“I think that they’re lying. (DeBerry is) not in their pocket. She’s not a puppet. She hasn’t had any conversation with the mayor. How does she know what his moves are going to be?” said Ibie Hart, DeBerry’s campaign manager, who stressed that the 2nd District candidate is deeply rooted in community schools.

When asked about the effect of negative ad campaigns of union-aligned political action committees, 9th District candidate Lanetta Thomas, endorsed by CTU, said, “We’re spending more money on these ads than our children, and I don’t agree with it … anything (negative) with me in particular on there, I never approved it.”

CTU and their affiliated interest groups have spent $8,000 on Thomas’ campaign. Though she works in media relations, Thomas reiterated she has had no control over any ads that aren’t affiliated with her committee Friends For Lanetta Thomas, which has directly raised $14,359 on her campaign, records show. CTU The committee for her opponent, CTU-opposed Miquel Lewis has raised $28,300, according to records, and charter-aligned groups have spent hundreds of thousands more on advertising supporting Lewis.

Flagrant negative local campaigns that leverage national issues have become more common in recent years, including leveraging national issues for local races, said Matt Dietrich, public information officer at the Illinois State Board of Elections. Though he said in some cases it can also backfire.

“You’ve effectively given your future opponent even more promotion and put them more prominently into the public mind,” Dietrich said.

Project 2025, spearheaded by the Heritage Foundation the American conservative think tank, is a layered blueprint for the next president’s plans to completely overhaul the executive branch, targeting abortion and immigration. Though people who follow national politics may not be familiar with its detailed proposals, many know it by name. The former president’s campaign has tried to distance itself from Project 2025, but Democrats have used it frequently as short-hand for what Trump might do if elected.

Rosenfeld, who has had her face plastered on the Trump ads and is running for school board in the 4th District, said all the people targeted as being Project 2025 supporters are longstanding Democrats who have been involved in education for a long time. She is a Democrat and is married to 47th Ward Democratic Committeeman Paul Rosenfeld. Still, she said she’s had people walk up and ask her if Trump endorsed her. Rosenfeld is endorsed by Urban Center Action, a centrist group favored by charter school interests.

“It just doesn’t make sense,” she said. “It takes away from talking about student experiences, student outcomes, student voices, families that have put everything into sending their children to Chicago Public Schools.”

She wonders: “If CTU is willing to do this, how are they going to run the school board? Where’s the integrity, where’s the transparency?”

Bruce Leon, a 2nd District candidate who is mostly self-funding, called the negative ads “over the top.” He said he recently got a call from a business colleague who told him, “Even if you’re a liberal Republican, I would vote for you. I can’t vote for you if you’re a MAGA person, just tell me the truth.”

“So if you want to attack me and say, ‘Bruce Leon wants to continue charter and wants to continue magnet schools like Disney and blah, blah, blah, don’t vote for him.’ Like that’s legitimate, right? They don’t even mention one issue (in the mailers),” Leon said.

The candidates being targeted have completely separate political agendas from Trump, despite the flurry of advertising, said Angel Gutierrez, who is running for school board in the 8th District. He said the messaging makes him angry.

“But I do appreciate the increased name ID that they’ve given me,” Gutierrez joked.

He, like Rosenfeld, is endorsed by Chicago Democrats for Education, a political action committee launched in late September as a counterpoint to CTU.

“Collectively, our seven candidates have raised about $500,000, but I’d say 99% of the spending of that on our ads is all positive ads,” said the director of that group, Hugo Jacobo.

Jacobo said his ads are “not focused on all this negative stuff” though he said they have been calling the opposition candidates “completely beholden to CTU.”

He said he wasn’t surprised when he saw the ad campaign against CTU-opposed candidates kick off in the fall.

“I knew that this was exactly what CTU and (President) Stacy Davis Gates were going to do. They were going to call them all Republicans,” Jacobo said.

CTU, for its part, has said charter-aligned groups are inserting undue influence in the election through out-of-state contributions by billionaires. They haven’t backed down from their Project 2025 claims.

“If it walks like a Republican, talks like a Republican, and is endorsed by Republicans, it’s probably a duck. If candidates don’t want to be associated with Project 2025, they shouldn’t accept their funds and promote its agenda,” said Hilario Dominguez, CTU’s political coordinator.

With the presidential election just days away, everything feels more uncertain, said Bruce Newman, professor of marketing at DePaul and editor and chief of the Journal of Political Marketing.

“Local politicians, in a unique way, are reaching out to voters to elect them because they know they will be in a position to protect (voters) from the presidential policies,” Newman said.

Chicago Tribune’s A.D. Quig and Molly Marrow contributed.