Brandon Johnson’s initial appointment indicated he would be a pragmatic progressive

Brandon Johnson has been described as the most left-leaning and progressive mayor Chicago has ever seen.

His initial appointment tells a different story about how Chicago's 57th mayor came to govern.

They suggested Johnson might turn into a pragmatic progressive, concerned more about the art of the possible and getting things done than about staying true to ultra-liberal principles.

So far, Johnson has made four important appointments: Rich Guidice as the all-important chief of staff; State Senator Cristina Pacione-Zayas as deputy Guidice; John Roberson as chief operating officer; and Fred Waller as interim Chicago Police inspector.

The mayor-elect has also asked most department heads and agency heads Mayor Lori Lightfoot to stay put, at least for a few months, saying she's not ready to clean house yet.

Chief Financial Officer Jennie Bennett has informed Johnson's transition team that she intends to follow Mayor Lori Lightfoot out.

Sources say three candidates are running to replace him: Jill Jaworski, managing director of PFM Financial Advisers; Euriah Bennett, city finance director at Citigroup in Atlanta; and Jack Brofman, Jennie Bennett's lead rep.

Either of them is likely to convince Wall Street and business leaders who oppose Johnson's proposal to impose $800 million in new or increased taxes to finance the social programs that form the cornerstone of his non-violence strategy.

Johnson has been reaching out to business leaders since the election to smooth the hair and invite alternatives to his business tax proposals.

Guidice and Roberson were government officials who cut their teeth under former Mayor Richard M. Daley.

Waller rose from patrol officer to chief of patrol, chief of operations, and third-in-command of the Chicago Police Department during a 34-year career that began under former Mayor Harold Washington and his Police Supt. Fred Rice.

Only Pacione Zayas shares Johnson's progressive roots.

She was elected in 2020 to fill the Senate void created by the election of County Court Registrar Iris Martinez. Previously, he chaired the Erickson Institute's Policy and Leadership Department. He's an ally of Ald. Carlos Ramirez-Rosa (35), chairman of the City Council's Democratic Socialist Caucus.

Waller's appointment sent a message to the demoralized, overworked and underappreciated officers who have retired in droves.

Johnson spent the entire campaign distancing himself from his history of supporting the concept of defunding the police. Now, as mayor-elect, he needs to show the officers — whose unions are backing his opponent, Paul Vallas — that he'll stand by them.

Guidice and Roberson's election was designed to reassure the business community that supports and finances Vallas and the nearly two dozen Board members who also support Johnson's second-round opponent.

Ashlee Rezin/Sun-Times

Their extensive experience in government is expected to prove crucial to Johnson, a Cook County commissioner with no executive and city government experience.

Jason Lee, senior adviser to mayor Johnson's campaign and transition team, said anyone who was surprised by the initial appointment didn't listen enough to what the mayor-elect had to say during the campaign.

The ‘Three C's of a Johnson employee

Lee notes Johnson began his career in the office of Don Harmon of Oak Park, now president of the Illinois Senate. Johnson was also working for Ald at the time. Deborah Graham (29) before spending time as a teacher and paid organizer for the Chicago Teachers' Association.

“What he's trying to communicate on the campaign trail—which people might overlook because of some of the other narratives—is ‘collaborative, compassionate, and competent. Those were the three Cs he used to articulate his vision for recruiting – and all the recruits he's made so far fit those three Cs,” said Lee.

File John H. White/Chicago Sun-Times

Lee noted 75% of Chicago voters believed the city was “going in the wrong direction”. Johnson was determined to deliver on that change, he said.

“But to effect change, you have to understand the system you want to change. You must have deep and profound knowledge of what is possible, what can wait, what can be pushed. So you build a team that has the vision for transformation, but also the know-how to make that transformation real while maintaining the core functionality that city residents rely on,” said Lee.

After the 2008 election of Barack Obama, then-Speaker of the US House of Representatives Nancy Pelosi (D-Ca.) famously said, “The new president must rule from the middle.”

‘It's about doing something'

Lee was asked if Johnson shared Pelosi's philosophy on the need to “rule from the middle” and be more pragmatic than progressive.

“Pragmatism, to me, is essential to any effective progressivism. All pragmatism says, ‘I have a keen sense of the reality of what it takes to get things done, and I will organize myself and my actions around it so I can be an effective progressive,'” said Lee. whose mother is US Representative Sheila Jackson Lee, (D-Texas), a 28-year congressional veteran who is now running for mayor of Houston.

“Being progressive is not just about saying something. It's about doing something.”

Lee notes the city government is a giant bureaucracy, often resisting change. To make substantive change, you need “people with a vision of what's needed, what's possible and understand how to … navigate opportunities to move the ball forward,” he says.

“If you can do that without unnecessary de-stabilization, then you will build a political consensus. If there is too much de-stabilization, then you lose the political support needed for everything else.”

David Greising, president and CEO of the Better Government Association, wrote a column for the Chicago Tribune warning of what he calls “a lack of government experience” and the union roots of some of Johnson's transition team's early choices.

They include members of the International Service Employees Union whose affiliates are Johnson's second-biggest campaign contributors.

But Greising admitted to the Sun-Times that he may have taken the wrong conclusion and put too much stake in the transition team, because it was less important than who would co-govern with the new mayor.

“I went at him pretty loud saying, ‘These guys are not ready for prime time. I did point out – and I'm glad – that there's a lot more to come. Well, that ‘upcoming part' is pretty impressive. … We were told that Brandon Johnson may be more pragmatic than he appears as a candidate. And the degree to which he is able to be a pragmatist and a progressive will be a big factor in determining whether he is successful as mayor,” said Greising.

“He is aware of where a deficit or lack of experience as a manager might need to be shored up. And he seems to fill it with people who are qualified to be significant contributors to governance. … If he listened to these people and used their skills and their more mainstream views and matched it to where he was from, it could be a pretty interesting and successful administration.

‘Trying to strike a balance'

Ald. Brian Hopkins (2nd), who backed Vallas, was equally encouraged.

“He's trying to strike a balance. He was clearly determined not to make the previous mayor's mistake and alienate people,” Hopkins said.

“Politics is a sum game. So he is trying to augment his progressive Socialist base by appealing to the more moderate wing of the Democratic Party.”

Greising warned that Johnson's apparently pragmatic path was not without political risks. He pointed to the “serious political price” Mayor Lori Lightfoot paid for, as she put it, “walking away from her progressive image.”

During Round One of the mayoral draw, Johnson accused Lightfoot of “breaking every promise he made” to progressive voters.

“The hopes and wishes of working families have been ignored. This is what happens when you are not legally connected to the progressive movement. It doesn't surprise me that he broke that promise because he never believed it in the first place,” Johnson told the Sun-Times.

Ashlee Rezin/Sun-Times

“I didn't break my promise. I will be a bona fide progressive in this race” who can “organize and collaborate in a way that really brings us to the kind of economic justice this city needs”.

Johnson's details on Lightfoot include his face on the elected school board and his broken promises to reopen closed mental health clinics and increase real estate transfer taxes on the sale of upscale homes to create a dedicated revenue stream to reduce homelessness and create affordable housing.

He also cited Lightfoot's handling of a car wrecking operation that attempted to move from Lincoln Park to the predominantly black and Latino areas of the Southeastern Side.

The Lightfoot administration initially supported the move, triggering an ongoing federal civil rights investigation. The city's health department eventually refused permission to operate. Johnson lashed out at “a government willing to create toxic waste dumps… a place where black and brown people live.”

‘What he does most is communicate'

If Johnson can't deliver on all of his progressive promises, including a real estate transfer tax – which requires approval from state lawmakers – as well as a financial transactions tax – which Governor JB Pritzker opposed – Greising said the new mayor will have to rely on his formidable communication skills.

“Progressive people tend to be idealistic. They are often not very realistic about what they demand and expect. But it's his job to take them,” said Greising.

Comparing Johnson to Lightfoot, Greising said: “He's a very good communicator, and he's not. What Lightfoot fails to do is communicate the why and why of the decision. What he does best is communicate. He'll stand a better chance of keeping the progressives with him even if he has to make pragmatic compromises along the way.

Also weighing on Johnson's virtues are his progressive roots. He was one of them, said Greising.

Unlike Lightfoot, he added: “He's not a corporate lawyer.”