Lori Lightfoot was never the left’s candidate.

In fact, in Lightfoot’s landslide victory in April, her staunchest opposition came from Chicago’s activist left — community organizers, police reformers, affordable housing advocates. Lightfoot’s career path, from the U.S. attorney’s office to the Police Board to earning $1 million a year as a partner at Mayer Brown, made her look like The Man. The website Stop Lightfoot called her “a law-and-order candidate trying to run as a progressive.” On Election Day, she was confronted outside a polling place in Woodlawn by a South Side community organizer who demanded to know why she had skipped an affordable housing forum.

But Lightfoot didn’t run as a progressive. She ran as a reformer, the political outsider who promised to quash the Chicago Way, as exemplified by Ald. Ed Burke and all the mayoral candidates who took his money. (Lightfoot’s opponent, Toni Preckwinkle, ran as a progressive, but not a reformer.)

There is some overlap between reformers and progressives. Progressives love “good government,” because it takes power away from politicians, lobbyists, and corporations. But they’re not the same thing. So it’s no surprise that Lightfoot is still at odds with the left, and that some progressives who voted for her are already disillusioned.

The just-settled Chicago Teachers Union strike will likely be the first of many major confrontations between Lightfoot and progressives. The CTU has played a significant role in pulling the city’s politics to the left. After the 2012 teacher strike and Mayor Rahm Emanuel’s closing of 50 schools, the mobilized teachers’ union helped found United Working Families, a political action committee that endorsed five of the six socialist aldermen elected to the City Council this year. The CTU’s president, Jesse Sharkey, was once a member of the International Socialist Organization. And during the mayoral campaign, the CTU donated $300,000 to Preckwinkle, herself a former teacher.

During the strike negotiations, the CTU asked Lightfoot to support its plan for an elected school board, and a change in the state law that specifies which issues teachers can strike over.

“Are we really keeping our kids out of class unless I agree to support the CTU’s full political agenda wholesale?” the peeved mayor asked after a late night of bargaining.

The friends and enemies Lightfoot made during the strike won’t endear her to progressives, either. Sen. Elizabeth Warren, who is competing with Bernie Sanders for the left lane in the Democratic presidential primary, flew into Chicago to join teachers on the picket line. Chance the Rapper wore a CTU sweatshirt on Saturday Night Live, declaring his support for the strikers in his opening monologue. (Chance donated $450,000 to Amara Enyia in the primary, then endorsed Preckwinkle in the runoff.)

On the flip side, Lightfoot had the staunch support of the Chicago Tribune editorial board, which initially endorsed Bill Daley for mayor. In a press release this morning, the libertarian Illinois Policy Institute wrote that Lightfoot “deserves credit for trying to hold the line during tough negotiations, especially after offering such a generous initial contract.” And on Wednesday, education secretary Betsy DeVos tweeted a column by the Tribune’s Kristen McQueary that accused the union of sandbagging Lightfoot for political revenge: “CTU leaders who backed Chicago Mayor Lori Lightfoot’s rival in the last election certainly weren’t going to hand Lightfoot a victory for avoiding a strike,” she wrote.

Even Lightfoot’s proposal for a real estate transfer tax on sales over $500,000 — the definition of a progressive tax — is getting pushback from nine Democratic legislators. They say they won’t vote for it unless 60 percent of the proceeds are earmarked for fighting homelessness.

Lightfoot’s response? “Never going to happen, obviously … We’re not going to be in a situation in the near-term to be able to take 60% of a significant revenue stream off the table and devote it to any issue. There’s lots of issues that merit: homelessness, mental illness, violence reduction.”

In her budget message, Lightfoot also disappointed progressive aldermen when she failed to propose reinstating the city’s $4-an-employee corporate head tax.

Lightfoot may be in a no-win position with the left — that position being mayor. Throughout history, progressives have always considered themselves the opposition in Chicago. When he was chair of the Progressive Caucus, Ald. Scott Waguespack voted against the mayor as much as any alderman, according to Dick Simpson’s Rubber Stamp Report. The left hasn’t had a mayor it loved since Harold Washington.

Writing in the Chicago Reporter, Curtis Black suggested that progressives cut Lightfoot some slack. Her restaurant tax and ride share fee proposals are progressive, Black argued, as are her plans to reduce water bills and relax penalties for driving without a city sticker. (She’s also ending library fines.)

Black also warned that knee-jerk contrarianism could damage the left’s ability to promote its agenda.

“The mayor’s budget is not perfect, but it’s not all bad, and there’s a fair amount that deserves praise,” he wrote. “Lori Lightfoot is not actually Rahm 2.0. She can do better, as all of us can. But demonizing her — especially when it requires distortions of reality — may not be the best way to encourage that. That kind of demonization failed miserably in the mayoral campaign. And since Lightfoot remains popular, that strategy risks isolating progressive voices. That would be unfortunate, since they provide a vital perspective for the city’s future.”

Left, right, or center — and even after a teacher strike — she’ll almost certainly continute to endear more Chicagoans than the last mayor.

Changes to This Story November 4, 2019: An earlier version of this story stated that United Working Families endorsed three of the six socialist candidates elected in the 2019 aldermanic race. It endorsed five.

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