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Karen Lewis and Rahm Emanuel: Rocky relationship ‘started in one place and ended in another’

They exchanged profane insults. But Rahm Emanuel and Karen Lewis also enjoyed each other’s “dark sense of humor,” went to the ballet together, shared Jewish prayers and worked together to strengthen teacher pensions. They clashed, in part, because they were very much alike.

Chicago Teachers Union President Karen Lewis, left, at the City Club of Chicago in 2017; Mayor Rahm Emanuel, right, at a City Council meeting in 2018.
Chicago Teachers Union President Karen Lewis at the City Club of Chicago in 2017; Mayor Rahm Emanuel at a City Council meeting in 2018.
Sun-Times file photos

Their relationship “started in one place and ended in another.”

They exchanged profane insults. But they also enjoyed each other’s “dark sense of humor,” went to the ballet together, shared Jewish prayers and worked together to strengthen teacher pensions.

As mayor, Rahm Emanuel had a rocky relationship with Karen Lewis, then the president of the Chicago Teachers Union. It featured a seven-day strike and a record 50 school closings. They clashed, in part, because they were very much alike.

Lewis’ death was confirmed Monday after a long bout with brain cancer. She was 67.

“Karen and I were strong personalities — both of us. Strong-willed — both of us. We had an appreciation of the arts. We had a passion for children and education. … We loved each other’s sense of humor. Even in the most tense moments, we could make — not only jabs at each other and laugh, but jabs at other people around,” Emanuel recalled Monday.

“There were tough words said on both sides and there was retraction on both sides. … I learned a helluva lot from her. She has said the same. And in the learning from each other also came a lot of respect and admiration. … When she’s on the other side, she’s as wily and smart and strategic and funny and thoughtful as they come. The truth of the matter is, we are much, much more similar than dissimilar.”

Mayor Rahm Emanuel, during a visit to Marantha Church in September 2012, talks with reporters about the ongoing Chicago Teachers Union strike.
Mayor Rahm Emanuel, during a visit to Marantha Church in September 2012, talks with reporters about the ongoing Chicago Teachers Union strike
Rich Hein/Sun-Times file

The stage for their tempestuous relationship was set even before Emanuel took office in 2011.

Emanuel famously used profanity in an early confrontation with Lewis, infuriated her members by canceling a previously-negotiated 4% pay raise for teachers, then added insult to injury by persuading the Illinois General Assembly to raise the strike-vote threshold to 75%.

Chicago teachers were so incensed, 90% voted to strike — the first in 25 years. They remained on the picket lines for seven days and got the better of the mayor when the strike was settled.

Chicago Teachers Union President Karen Lewis casts her ballot during a strike authorization vote in June 2012.
Chicago Teachers Union President Karen Lewis casts her ballot during a strike authorization vote in June 2012.
Associated Press

Emanuel has told associates if he could undo only one decision as mayor, it would be canceling the teacher pay raise. The move was seen as sheer arrogance. So was Emanuel’s pre-strike decision to force immediate implementation of the longer school day.

On Monday, the former mayor acknowledged his early mistakes turned Lewis into a strike-leading folk hero who might have denied Emanuel a second term if not for being diagnosed with a brain tumor in 2014.

“We dealt with two things. The financial books and the educational books were not in order. ... I made a pledge we were gonna have a full school day and a full school year and I made a pledge every child will get kindergarten. And I was gonna fix the finances. Those seven days were about those fights,” Emanuel said.

“But the way I went about it is totally is on me. ... We had to deal with the financials … but I do own that it threw the relationship off.”

After denouncing Emanuel as Chicago’s “murder mayor,” Lewis underwent surgery even as her supporters collected signatures to get her on the ballot. She then threw her support to Jesus “Chuy” Garcia, who forced Emanuel into a runoff and lost.

Buttons that a Karen Lewis spokeswoman in 2014 said were being created by union members and other supporters who want the CTU president to run for mayor.
Buttons that a Karen Lewis spokeswoman in 2014 said were being created by union members and other supporters who want the CTU president to run for mayor.
Sun-Times file

Monday, Emanuel said he has no idea whether he would have lost to the charismatic union leader with a tongue and wit even sharper than his own.

Instead, he chose to focus on what they accomplished together after his 2015 re-election.

At first, he tried to negotiate a contract with the CTU that included the equivalent of a 7% pay cut for all teachers.

When Lewis “couldn’t sell it,” Emanuel “re-calibrated” to end the 7% “pension pick-up” — but only for new hires.

That convinced the Illinois General Assembly to give the Chicago Public Schools a $450 million cash infusion and bankroll teacher pensions going forward.

“She and I came to an agreement in 2015 on major changes. And it’s not an accident that, because of those changes, that Chicago teacher pensions are one of the best-funded pensions between the state and the city of Chicago because of Karen Lewis and Rahm Emanuel,” Emanuel said.

“They worked a year without a contract until we could find both the political capacity to make the changes as well as the right type of changes. ... By 2015, the entire friendship, relationship trust level was on a different level.”

Pressed again on whether a healthy Karen Lewis would have denied him a second term, Emanuel said, “As she would say, `That’s nothing but Midrash. It’s hypothetical. It’s a story made up of the Talmud.”

Karen Lewis attends a Garcia campaign event at the New Mount Pilgrim Missionary Baptist Church 4301 W. Washington St., in April 2015.
Chicago Teachers Union President Karen Lewis declined to run for mayor in 2015, deciding instead to endorse Jesus “Chuy” Garcia, who forced a runoff election with Rahm Emanuel. Here, Lewis attends a Garcia campaign event at the New Mount Pilgrim Missionary Baptist Church 4301 W. Washington St., in April 2015.
Sun-Times file