Lightfoot Stands Alone, Talks Like 'Boss' She Doesn't Want To Be

CHICAGO — After the summer's second round of downtown looting, a longtime political insider rang. "Man, I'm worried about Chicago," he said.

We discussed reasons for anxiety. The lootings, the shootings and the murders, of course. The looming city budget crisis and the Chicago Public School's proposed property tax increase. The dried-up convention and tourism business, too. And whether the latest attack on the Magnificent Mile has rich, white folks planning to run for the border.

Like Lightfoot, the insider once worked for various subsidiaries of the Richard M. Daley's version of the Chicago Democratic Machine.

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"Say what you want about Daley, man, but when s--- went down, he owned it. He got people in the room. When the mayor called at 9 o'clock saying he wanted to talk, whoever it was got to City Hall by 9:30. He got things done," the insider said.

"I hate to say it. And don't mean it in any 'I miss patronage and corruption' kinda way. But the whole thing makes me miss having a Chicago boss."

I can't say that I feel the same. I'm too troubled by the accepted level of corruption, the clouted deals, the Hired Truck scandal, the nepotism, the patronage, the blind eye to police brutality and misconduct and, worst of all, the ascension of Rahm Emanuel associated with the Daley administration.

But I understand the insider's point. Mike Royko once explained to Studs Terkel the reason Chicagoans so revered its political mythology he debunked in the biography of Mayor Richard J. Daley, "Boss."

"The city likes the myth. We like things big. We like to say we're better at this and better at that. Once it started, during his first term, that Daley could get a city moving, we wanted to believe this, despite the steady flow of evidence to the contrary that he's none of the things the myth-makers have made him out to be," Royko said in the 1971 interview.

"That he's a great administrator, a man of the people. That he can solve problems where other mayors can't. I think the city wanted to believe that. It's reassuring to think that we have someone that keeps the city going."

The insider isn't alone in longing for comfort of the political illusion a majority of Chicago voters once trusted to guide the city through tumultuous times. Another operative with Democratic Party pedigree told me Lightfoot's lack of public supporters makes her look weak in a time of trouble.

"The city's in absolute chaos, there's no other way to describe it," he said. "And the mayor's pointing fingers. She stands alone. Who's with her?"

Well, not the Cook County Democratic Party boss she trounced in a landslide. Lightfoot can't count on the Cook County state's attorney whom she has endorsed for re-election — and gave public tongue-lashing for being weak on criminals.

Gov. J.B. Pritzker is a fake friend of City Hall who's mostly available for ribbon-cutting photo ops in African American neighborhoods. Lightfoot has a beef with Illinois Attorney General Kwame Raoul. She's at odds with the police and teachers unions. Black Lives Matter Chicago activists attack her.

The City Council's Democratic Socialists despise the mayor. A band of rogue aldermen is plotting to wrestle away her City Council voting majority. And the cop-heavy wards that elected her in 2019 — well, let's just say they're not a lock to support Lightfoot's re-election bid.

Her inner circle is packed with out-of-town bureaucrats and holdovers from Emanuel's administration. Her strongest City Council allies don't have powerful, get-out-the vote political organizations.

Still, Lightfoot talks like a boss. Makes demands like a boss. Cusses-out aldermen and President Donald Trump like a boss. And puts weaselly TV reporters in their place like a boss. She even ends sentences by saying, "Period," like a boss.

So, I asked the mayor if in tumultuous times like these, when Chicago Democrats have splintered in warring factions, if our fearful, chaotic city needs a boss, again?

"Chicago doesn't need a boss. Chicago doesn't want a boss," Lightfoot said. "Chicago wants ethical, strong, transparent leadership. … [Voters in 2019] were given a very stark choice, and they voted resoundingly for a change in direction. … That is still very much the case."

The mayor went on to say that her success is uniting people — not fellow Democrats, necessarily. Especially, ward bosses who say the city is losing confidence in her when cameras are rolling. She's talking about everyday Chicagoans, like the people who stop her on the street to offer their straight take on the state of the city and what they hope the future holds.

"They want to be safe. They want to feel the city hears them," Lightfoot said. "That their lived experience is reflected in public policy, and that we are going to see our way through this most difficult confluence of very challenging circumstances."

With our city feeling increasingly on the brink, there's comfort in Lightfoot's message.

Hopefully, it's not another Chicago myth.

Mark Konkol, recipient of the 2011 Pulitzer Prize for local reporting, wrote and produced the Peabody Award-winning series, "Time: The Kalief Browder Story." He was a producer, writer and narrator for the "Chicagoland" docu-series on CNN, and a consulting producer on the Showtime documentary, "16 Shots.

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