Analysts weigh in on troubles Chicago Mayor Brandon Johnson has been facing lately

With unflattering headlines lately, analysts say Mayor Johnson is at a fork in the road

CHICAGO (CBS) -- Mayor Brandon Johnson decided not to attend the funeral for fallen Chicago Police Officer Enrique Martinez on Monday after a back-and-forth with Martinez's family—who had asked him not to attend.

That headline is just one out of his office—coming on the heels of a 50-0 rejection by the City Council of the the mayor's proposed $300 million property tax hike for the 2025 budget.

Meanwhile, the Wall Street Journal named Mayor Johnson the "worst mayor in America," The political winds have drifted to the point where even staunch Johnson supporters are questioning what is going on.

For all those reasons, political analysts say Johnson is at a fork in the road 18 months into office. Analysts say navigating that fork in the road requires a reset of how Johnson governs and the people with whom he surrounds himself.

"This is an inflection point, and it's a reflection point—because he really needs to reflect on what he wants his legacy to be," said Democratic political strategist Delmarie Cobb.

When asked what grade she would give Mayor Johnson, Cobb said a B minus.

Political Science Professor Stephen Maynard Caliendo was less generous.

"The honeymoon is well over. There has to be some wins coming," Caliendo said. "If I have to give him a grade like a professor, I guess I'd be sitting at a C minus or a D at this point."

Cobb and Caliendo had similar observations of what has gone wrong in the Johnson administration.

"What's really important, of course, is to put the right people around you," said Caliendo.

"There are some rookie mistakes that I don't think he needed to make if he had had some seasoned people around him," added Cobb.

For one example, Cobb pointed to the hasty replacement of school board members just days after mass resignations.

"You don't fire the school board, or they leave on Friday and then on Monday, you're announcing their replacements—and do a good, thorough job of vetting the people whom you're going to have replace them," Cobb said.

As for the funeral of Officer Enrique Martinez, attended by former Mayor Richard M. Daley, political analysts wonder why Johnson initially refused the Martinez family's request that he not attend.

"He's making a series of curious decisions that doesn't seem to acknowledge that he has some public opinion trouble," Caliendo said.

And then over the weekend, the Wall Street Journal's issued an editorial headlined, "America's Worst Mayor Keeps Losing." Cobb had a cautionary note about the judgment in that headline.

"Did they say that when [Rahm] Emanuel was the mayor? Did they say that when [Richard M.] Daley was the mayor? No, they didn't say that," Cobb said. "As long as you're doing harm to Black people, you're not the worst, because as long as white people have the comforts and amenities, then you're wonderful."

Cobb says of Johnson that he has "done no harm." While some tell her that is a low bar from which to judge, she countered with an observation former Mayor Rahm Emanuel—castigating him for closing 50 schools and half of the city's mental health clinics, and, in her words, trying to "cover up the murder" of Laquan McDonald by a Chicago Police officer.

Cobb also castigated Mayor Richard M. Daley, saying he disinvested in the Black community for 20 years—leading to the loss of a quarter million African Americans from the city since 2000.

Cobb said Johnson undeniably has self-inflicted wounds, but she said that is part of the framework against which Johnson needs to be judged.

CBS News Chicago reached out, and the Mayor's office had no comment on the Wall Street Journal editorial.

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