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Brandon Johnson has been portrayed as the most left-leaning, progressive mayor Chicago has ever had.

His early appointments tell a different story about how Chicagos 57th mayor might govern.

They suggest Johnson may turn out to be a pragmatic progressive, more concerned about the art of the possible and getting things done than he is about staying true to ultra-liberal principles.

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

The mayor-elect has also asked most of Mayor Lori Lightfoots department heads and agency chiefs to stay on, at least for a few months, saying he is not ready to clean house.

Chief Financial Officer Jennie Bennett has told Johnsons transition team she intends to follow Mayor Lori Lightfoot out the door.

Sources said three candidates are in the running to replace her: Jill Jaworski, managing director of PFM Financial Advisers; Euriah Bennett, director of municipal finance at Citigroup in Atlanta; and Jack Brofman, Jennie Bennetts top deputy.

Any of them would likely be reassuring to Wall Street and to business leaders dead set against Johnsons proposal to impose $800 million in new or increased taxes to bankroll social programs that form the cornerstone of his anti-violence strategy.

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

Guidice and Roberson are government lifers who cut their teeth under former Mayor Richard M. Daley.

Waller worked his way up 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 Johnsons progressive roots.

She was chosen in 2020 to fill the Senate vacancy created by the election of Circuit Court Clerk Iris Martinez. Before that, she led the Erickson Institutes Policy and Leadership Department. Shes an ally of Ald. Carlos Ramirez-Rosa (35th), chairman of the City Councils Democratic Socialist Caucus.

State Sen. Cristina H. Pacione-Zayas speaks at a special session for reproductive health rights after news of the Supreme Court overturning Roe v. Wade last year.

Brian Rich/Sun-Times file

The Waller appointment sent a message to demoralized, overworked and under-appreciated officers who have been retiring 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 needed to demonstrate to officers whose union supported his opponent, Paul Vallas that he would have their backs.

The selections of Guidice and Roberson were designed to reassure a business community that backed and bankrolled Vallas and the nearly two dozen Council members who also supported Johnsons runoff opponent.

Rich Guidice (second from left), then first deputy of the citys Office of Emergency Management and Communications, attends the Chicago Police Department roll call meeting at Taste of Chicago in 2018.

Ashlee Rezin/Sun-Times file

Their extensive government experience is expected to prove critical to Johnson, a Cook County commissioner who lacks executive and city government experience.

Jason Lee, a senior adviser to Johnsons mayoral campaign and transition team, said anyone surprised by the early appointments wasnt listening closely enough to what the mayor-elect was saying during the campaign.

Lee noted Johnson began his career in the office of Don Harmon of Oak Park, now president of the Illinois Senate. Johnson also worked for then-Ald. Deborah Graham (29th) before spending time as a teacher and a paid organizer for the Chicago Teachers Union.

What he tried to communicate on the campaign trail which people might have glossed over because of some of the other narratives was collaborative, compassionate and competent. Those were the three Cs that he used to articulate his vision for hires and all of the hires hes made so far fit those three Cs, Lee said.

John Roberson, shown in 2004 at OHare Airport after being named Chicagos aviation commissioner.

John H. White/Chicago Sun-Times-file

Lee noted 75% of Chicago voters believe the city was headed in the wrong direction. Johnson is determined to deliver that change, he said.

But to make change, you have to understand the system you wish to change. You have to have a deep, intimate knowledge of whats 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 simultaneously maintaining the core functions of the city residents rely upon, Lee said.

After the 2008 election of Barack Obama, then-U.S. House Speaker Nancy Pelosi (D-Ca.) famously said, A new president must govern from the middle.

Lee was asked whether Johnson shares Pelosis philosophy about the need to govern from the middle and be more pragmatic than progressive.

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

Being a progressive is not just about saying things. Its about doing things.

Lee noted city government is a giant bureaucracy, often resistant to change. To make substantive change, you need people with vision about what is needed, what is possible and understand how to ... navigate the opportunities to move the ball forward, he said.

If you can do it without unnecessary de-stabilization, then you will build political consensus. If theres 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 sounding the alarm about what he called the scant government experience and union roots of some of Johnsons early transition team choices.

They included members of a Service Employees International Union whose affiliates were Johnsons second-largest campaign contributor.

But Greising acknowledged to the Sun-Times he might have jumped to the wrong conclusion and put too much stock in the transition team, since it is less important than who will govern alongside the new mayor.

I went at him fairly hard saying, These people arent ready for prime time. I did point out and Im glad that theres more to come. Well, the more to come part of it has been pretty impressive. It says to us that Brandon Johnson may be more of a pragmatist than he appeared to be as a candidate. And the extent to which he is able to be both a pragmatist and a progressive will be a big factor in determining whether he is successful as a mayor, Greising said.

Hes aware of where his deficits or lack of experience as a manager may need some shoring up. And he seems to be filling that with people who are qualified to be significant contributors to the administration. If he listens to these people and takes on board their expertise and their more mainstream views and matches that up with where hes coming from, it could be quite an interesting and successful administration.

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

Hes trying to strike a balance. Hes clearly determined not to make the mistakes of the previous mayor and alienate people, Hopkins said.

Politics is a game of addition. So hes trying to add to his progressive, Socialist base by appealing to the more moderate wing of the Democratic Party.

Greising warned the pragmatic path Johnson appears to be paving is not without political risk. He pointed to the serious political price Mayor Lori Lightfoot paid for, as he put it, walking away from her progressive image.

During Round One of the mayoral sweepstakes, Johnson accused Lightfoot of breaking every single promise she made to progressive voters.

The hopes and desires of working families have been ignored. This is what happens when you are not legitimately connected to the progressive movement. Its not a surprise to me that she broke those promisesbecause she never believed them from the beginning,Johnson told the Sun-Times.

Mayor-elect Brandon Johnson introduces former CPD third-in-command Fred Waller as his choice to be interim police superintendent, effective May 15.

Ashlee Rezin/Sun-Times file

I dont break promises. I will be the bonafide progressive in this race who can organize and collaborate in a way that actually gets us to the type of economic justice that this city needs.

Johnsons bill of particulars against Lightfoot included her about face on an elected school board and her broken promises to reopen shuttered mental health clinics and raise the real-estate transfer tax on high-end home sales to create a dedicated revenue source to reduce homelessness and create affordable housing.

He also cited Lightfoots handling of the car-shredding operation seeking to relocate from Lincoln Park to a predominantly Black and Latino area on the Southeast Side.

Lightfoots administration initially backed the move, triggering an ongoing federal civil rights investigation. The city health department eventually denied the operating permit. Johnson slammed an administration that was willing to set up a toxic waste dump ... where Black folks and Brown folks reside.

If Johnson is unable to deliver on all of his progressive promises, including that real estate transfer tax which needs approval from state lawmakers as well as a financial transaction tax opposed by Gov. J.B. Pritzker Greising said the new mayor will have to rely on his formidable communication skills.

Progressives tend to be idealists. They often are not very realistic about what they demand and expect. But its his job to bring them along, Greising said.

Comparing Johnson to Lightfoot, Greising said: Hes a really good communicator, and she was not. What Lightfoot failed to do was communicate the whys and wherefores of those decisions. What he does best is communicate. Hell have a better chance of keeping the progressives with him even if he has to make pragmatic compromises along the way.

Also weighing in Johnsons favor is his progressive roots. Hes one of them, Greising said.

Unlike Lightfoot, he added: Hes not a corporate lawyer.

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Brandon Johnsons early appointments suggest hell be a pragmatic ... - Chicago Sun-Times