Official leaving Chicago Mayor Brandon Johnson's administration for Obama Foundation

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CHICAGO — Mayor Brandon Johnson's chief operating officer is leaving the administration to join the Obama Foundation, ending weeks of speculation — and pushback — over his potential appointment to lead the CTA.
The Obama Foundation told the Tribune John Roberson will join its leadership team as executive vice president starting July 7. And Johnson spokesperson Cassio Mendoza confirmed Roberson's last day in the mayor's office will be June 20.
'I want to thank John Roberson for his dedication and service to our city over these past two years,' Johnson said in a statement. 'I wish him the best of luck as he continues to serve our city in his new role at the Obama Foundation.'
Roberson did not immediately respond to a request for comment Monday.
A member of the administration since the freshman mayor assumed office, Roberson is the last official within Johnson's inner circle with previous City Hall experience. His resignation was announced in a senior staff call Monday morning, sources said.
'John has the right background, experience and reputation to lead the operations of the Obama Presidential Center as we prepare to welcome the people of Chicago and the world to our campus next year,' Valerie Jarrett, CEO of The Obama Foundation, wrote in a statement. 'John is well known for his rigor and commitment to excellence and his values-based leadership approach which aligns strongly with President Obama's vision.'
For the last several weeks, Roberson had been the subject of opposition from transit advocates who feared the Johnson administration was angling to install him as the next president of the CTA. The agency has been left without a permanent leader since late January, when embattled president Dorval Carter retired.
Transit activists sought a thorough search process for the agency's new head, whom they hoped would have previous experience leading a mass transit system. Johnson's team has said they did do a national search and he has not made a decision.
Earlier this spring, Roberson was also rumored to be Johnson's next Chicago Department of Aviation commissioner. In the end, he was tapped for neither the Aviation nor the CTA role, and his exit from city government leaves the Johnson administration without any old-school City Hall bureaucrats among his top advisers.
It also leaves a giant question mark on how the course of a looming budget crisis within for the CTA will play out. The Illinois General Assembly adjourned this month without a solution to the estimated $771 million budget gap for Chicago-area transit agencies after negotiations fell apart at the eleventh hour.
Some Johnson critics said the trepidation over CTA's leadership under Johnson, who defended Carter throughout his controversial reign, impeded the transit agency's case before lawmakers that it can be trusted with more revenue to stave off the fiscal cliff. The mayor retorted last week that was a 'poor analysis' but did not say whether he will name the next CTA president before Springfield reconvenes to hammer out its transit package.
'I have not made a decision on who our appointment is going to be,' Johnson told reporters last week.
Roberson's transition into the nonprofit sector comes after wearing multiple hats over the course of his government career, including commissioner of the Aviation, Buildings and Sewers departments under Mayor Richard M. Daley. He stepped down from city government in 2005 after he was named as a cooperating witness in a federal investigation into fraud in city hiring and promotions, though he denied that his role in the probe was behind his decision.
Afterward, Roberson served as a top aide under Cook County Board President Toni Preckwinkle and Ald. David Moore, 17th, before returning to City Hall to join the Johnson administration in May 2023. As COO, his main task has been overseeing the nuts and bolts of city operations and ensuring that government services run smoothly.
The most visible role Roberson took on in that respect was managing the behind-the-scenes preparations for the Democratic National Convention's arrival in Chicago last August, when the mayor was thrust into the national spotlight and concluded the made-for-TV week of events with relatively high marks for how the city was portrayed on the national stage.
A former organizer with the Chicago Teachers Union, Johnson took office after running as a firebrand progressive and had appointed Rich Guidice and Roberson as the two City Hall veterans among his top deputies. Their hires were seen as reassurance to members of the business community who worried the new mayor would shake up city government too much by only bringing in allies from his activist grassroots coalition.
Those familiar with both Roberson and other top Johnson aides' thinking said the City Hall veteran at times clashed with mayoral staffers from more progressive grassroots backgrounds.
Guidice, also the former head of the city's Office of Emergency Management and Communications, left as Johnson's chief of staff in April 2024 after less than a year on the job and was replaced by Cristina Pacione-Zayas, who rose up among the Northwest Side progressives and served as a state senator before joining the Johnson administration in 2023.
Asked about Roberson's apparent tensions with progressives in the Johnson administration, Guidice said he never saw direct clashes but defended his former colleague and friend of more than two decades.
'They're losing someone with institutional knowledge in the administration, who knows the day-to-day operations of the city,' Guidice said. 'He was pretty aligned with my way of thinking, I would say, and my understanding of city government.'
In the Obama Foundation release, Roberson said he's looking forward to his new role. 'As a son of the South Side, I couldn't be more proud to build on the tremendous accomplishments of the OPC team and deliver this game-changing institution to our community and for our great city,' he said.
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(The Tribune's Gregory Royal Pratt contributed reporting.)
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