Fifteen years ago, Dan Montgomery and Karen Lewis set out on a road trip to Springfield determined to force changes to a bill they saw as an attack on teacher unions, particularly the one in Chicago.
Montgomery, an English teacher in Skokie, had just been elected president of the Illinois Federation of Teachers. Lewis had just taken over Chicago’s Local 1 — the largest chapter under the IFT’s umbrella. Montgomery said Lewis eyed him skeptically, worried he was a complacent union leader like the one she had just defeated in Chicago.
On that roadtrip, they kept the conversation light. “I had opera CDs in my car, so that’s what we talked about,” Montgomery recalls.
A decade and a half later, Montgomery has worked to connect the Chicago Teachers Union with educators in the rest of the state, and he has helped thousands of teachers unionize.
With the education landscape transformed in Chicago and Illinois, Montgomery is stepping down from the IFT to take a new job, and CTU President Stacy Davis Gates is running to replace him.
At the IFT convention this weekend, delegates from locals across the state will elect a new leader. Davis Gates is running for the top spot as part of a slate that represents Southern Illinois, the northern suburbs of Chicago and higher education workers. Davis Gates would remain CTU president.
Montgomery said he does not know of other candidates, but Davis Gates’ slate could be challenged on the convention floor.
Gates, an outspoken Black woman in charge of the progressive, aggressively activist CTU, is a lightning rod for conservatives — and some have already described her possible election as a power grab.
But up until 20 years ago, the CTU president was typically also the IFT president. IFT represents more than 100,000 teachers, support staff and public employees at state agencies, including the Illinois State Board of Education, the comptroller’s office and the secretary of state’s office.
Montgomery said Davis Gates is planning on distributing work and power among the IFT executive board in a de-centralized leadership model.
Montgomery pointed out he came from what he calls a militant local. An English teacher at Niles North High School, he’d been on strike six times and helped to negotiate strong contracts.
As head of the IFT, he wasn’t about to sit down and become a complacent leader.
“I had big hopes,” he said. “I wanted to make the IFT more powerful and more active.”
Montgomery won Lewis and her leadership team over.
“I think they realized, ‘This guy’s for real,’” Montgomery said. “‘He is one of us, he believes in the power of the union, and that we should have ambitions as a union.’”
As the CTU captured the national stage with its “common good” negotiating, Montgomery was in the background holding the statewide organization together. He said one of his biggest achievements was getting every local to see the value in what CTU was fighting for.
“You have to have CTU connected to the south, and you have to have the suburbs connected to the CTU and the central part,” he said.
Under Montgomery, IFT has grown with 30 new locals and 8,000 more members. He was at the table as the state negotiated a new funding formula, and he’s been at the side of many locals as they threatened to strike or went on strike. He was at the podium with Lewis at rallies and then, after she died in 2021, stood with her successors.
Montgomery said this is a challenging moment for teachers and other public service employees with the federal government pulling back funding and increasing immigration enforcement. Two locals are in tough contract fights. And many school districts have had to make cuts and are looking to the state to increase funding for education.
While the IFT faces external threats, Montgomery said the organization has a lot of young leaders who are ready to seize the moment.
“It’s so strong that I felt, now is the time,” said Montgomery, who will become executive director of the American Library Association.
The Illinois Education Association, which is the largest teachers union in the state with more than 130,000 members, also has a new president after its leader unexpectedly died in September.