Mayor Brandon Johnson losing his savvy chief of staff after less than a year in office

When Mayor Brandon Johnson chose City Hall lifer Rich Guidice to serve as his chief of staff, it sent a reassuring message to the business community and everybody else fearful of the most progressive mayor in Chicago history.

A savvy and seasoned veteran who knows city government like the back of his hand would be steering the ship through transition waters. 

The fact that police officers and firefighters among the most leery of Johnson knew and trusted Guidice from his tenure as executive director of the city’s Office of Emergency Management and Communications was an added plus. They assumed that Guidice, who has seen Chicago through countless special events, would guide the new mayor and Chicago through the Democratic National Convention in August and all of the protests that come with it.

On Thursday, Guidice abruptly pulled the plug on those assumptions. After nearly 33 years, he’s leaving city government to start a new job in April that he refused to identify.

“This has been the dream of a lifetime. As a kid growing up in the Chicago, I always felt, at least in my neighborhood and circles, that working for the city was the ultimate job to have. Being able to advance the way that I’ve been as commissioner and as chief of staff ending my career. It’s really been an exciting journey. Lifelong learning. I’m grateful to have had the opportunity,” Guidice, 55, told the Sun-Times.

“Every day, there’s a new challenge taking place in the city. We’re constantly pivoting and making decisions. ... The DNC is front and center. That's gonna take up a lot of energy. ... I’m confident … people are going to remain in place that are going to be able to advise the mayor and help him make all of these critical decisions. And just because I’m not on the city payroll doesn’t mean I’m not going to make myself available. It’s just time for me to try something different.” 

For whatever reason, Guidice is abandoning ship at a turbulent time for Johnson. 

The mayor suffered a humiliating setback this week when Chicagoans voted 53.6% to 46.4% against his binding referendum that would have authorized the City Council to raise the real estate transaction tax to create a dedicated revenue stream to combat homelessness.

Guidice refused to say where the mayor would turn next to replace the estimated $100 million in annual revenue he had hoped to raise by taking the first major step toward his tax-the-rich agenda. He called it a "work in progress." So are the requests by the White Sox and Bears for massive taxpayer subsidies to help bankroll their demands for new stadiums.

He would only say, "We're excited to still be in conversations with both of those entities."

On May 16, Johnson will celebrate his first anniversary in office. 

The tumultuous year has been dominated by a surge in robberies, opposition to his tax policies from the business community and by a migrant crisis that has divided Chicago, stretched city resources and strained the relationship between Johnson and Democratic Gov. J.B. Pritzker and between the mayor and City Council members. 

Twice, Johnson has been forced to cast tie-breaking City Council votes. Once to rescue a non-binding resolution calling for a cease-fire in Gaza, an effort that alienated Jewish leaders. The other to spare his former City Council floor leader and hand-picked Zoning Chair Carlos Ramirez-Rosa (35th) from censure after Ramirez-Rosa was resigned and apologized for bullying and intimidating his colleagues. 

Johnson has also been slow to assemble his own cabinet and make the transition from campaigning to governing while adjusting his communications strategy to accommodate the difference between the two.

Asked how he would characterize the first year, Guidice acknowledged the rocky road. 

“It’s a new administration. You’ve got a lot of people who are new to government and government processes. I wouldn’t say everybody expected everything to go smoothly by any means. We’ve been faced with many challenges,” Guidice said. 

“A lot of energy has been put into the asylum-seeker mission. … Spring and summer, we had 9.1 [inch] record rainfall. … NASCAR being a new event was something that we had to put a lot of attention on. We were able to get through a lot of those hurdles. So the mayor going into this year, this summer, has a good understanding of what to expect. I’m leaving him in a good place to be successful in 2024.” 

In a statement, Johnson praised Guidice as a “steady and guiding force and a mentor to many.”

Senior mayoral adviser Jason Lee said of Guidice's departure:  

"Today is about...taking the things that Rich has been able to contribute to this administration and carrying it forward. There are a lot of relationships he's helped us build. A lot of insights into how different things work."  

“I’m not thinking in terms of loss," Lee said. "I’m thinking in terms of what we’ve gained."