Fifteen years ago, Dan Montgomery and Karen Lewis set out on a road trip to Springfield determined to force changes to a bill that 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 the educators in the rest of

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