Understanding the Chicago School Board Fight in 2026

Re-printed from POLITICO Illinois Playbook by Shia Kapos - May 20, 2026

SCHOOL BRAWL: There’s a political battle brewing ahead of Chicago’s first fully elected school board races — and it’s pitting union leader Stacy Davis Gates against businessman and Democratic donor Michael Sacks.

The fight spilled into public view this week as candidates began filing petition signatures for the November election, marking the formal kickoff of a contest that could reshape power at Chicago Public Schools.

Last week, Davis Gates circulated a letter among the union’s roughly 800-member House of Delegates that was addressed to Sacks, urging him to stay out of the school board races. The catch, according to Sacks: He says he never actually received it.

‘Outsized influence’: Instead, someone connected to the union forwarded the letter to him, a spokesman for Sacks told Playbook. In it, Davis Gates warned that Sacks’ involvement in backing candidates could create “outsized influence [for] what is supposed to be a democratic process among Chicagoans to elect a school board” and asked Sacks not to get involved in the election, according to the letter obtained by Playbook.

The letter was only the latest salvo in a months-long campaign by Davis Gates and the Chicago Teachers Union to cast Sacks as a political foil. In union communications and public remarks, Davis Gates has accused him of “trying to subvert” the school board elections and supporting school closures, points that Sacks has denied.

This week, he fired back in his own letter, also obtained by Playbook.

“You … have defamed me,” Sacks wrote to Davis Gates. “You have done this on air, in print, on social media, and from the podiums and bully pulpit available to all of you,” he added, while also referencing Mayor Brandon Johnson as joining in the attacks.

Sacks also claimed Davis Gates wants it both ways: “No one in this city is focused more on spending big money on politics, or deploys that money more forcefully or creatively, than you do,” he wrote, arguing CTU is raising dues on teachers “to be able to spend more money on politics.”

Davis Gates doubled-down, telling NBC 5’s Paris Schutz, that Sacks should be focusing on “the gentleman occupying the White House on Pennsylvania Avenue,” rather than Chicago Public Schools. (Watch here at about 19 minutes).

Johnson’s team responded, “Our administration has consistently said that huge corporations and billionaires should pay their fair share to fund public education, community safety, and social services that strengthen communities and ease the burden on working people and taxpayers,” according to a statement, adding, “We stand in solidarity with advocates, including CTU President Stacy Davis Gates, who continue pushing for a fairer system that asks those with the greatest means to contribute more toward the investments communities rely on every day.”

And Sacks said his letter speaks for itself.

The escalating feud reveals just how high-stakes this year’s school board races have become.

“It’s going to be a pretty major fight,” Political analyst Dick Simpson told WGN 9’s Tahman Bradley. “They both have some different visions about how they think the schools should proceed.”

For the first time in city history, Chicago voters will elect all 21 members of the school board. The board had long been fully appointed by the mayor until a phased transition began last year. In 2024, voters elected 10 members while Johnson appointed the remaining seats, including the board president.

It’s big: This November, every seat — including board president – is on the ballot, marking some of the most consequential citywide races outside the mayor’s race (which occurs in 2027).

The players: The CTU is expected to line up behind Hilario Dominguez, though he has yet to file signatures. Others expected or already positioned to run include sitting board members Jennifer Custer and Jessica Biggs, former appointed vice president Sendhil Revuluri and attorney and charter school board member Victor Henderson.

A Democratic force: Sacks, meanwhile, remains one of Illinois Democrats’ most prolific donors and fundraisers. He served as chair of the local Democratic National Convention host committee in 2024, and he and his wife each contributed $1.1 million to fund the Chicago convention.

Sacks is also aligned with the Common Ground Collective, the political organization that has pushed back on some of Johnson’s progressive agenda.

And he’s become a lightning rod on the left over his support for the American Israel Public Affairs Committee. In a recent opinion piece, Sacks defended AIPAC against growing criticism within Democratic circles, writing: “Let’s be clear: The campaign against AIPAC is not a policy discussion. It’s a thinly disguised effort to make support for Israel politically toxic in the Democratic Party, to chase Jews and their allies out of our big tent coalition.”

The essay stirred debate among Democrats and frustrated some progressives, particularly because Sacks has also financially supported many liberal candidates and causes.

Painting a villain: Now, with the school board races underway, Davis Gates is intensifying her efforts to paint Sacks as the outside money threat looming over the elections.

Critics of the union see a contradiction: Davis Gates is attempting to discourage Sacks from backing candidates while simultaneously using the political muscle she has as both head of the CTU and the Illinois Federation of Teachers to boost her own preferred slate.