John Roberson was once one of Mayor Richard M. Daley’s favorites, hop-scotching from job to job before falling out of favor with the notoriously demanding mayor.
He lost his seventh and final job with Daley — as aviation commissioner — after his name turned up on a list of cooperating witnesses in the federal investigation of City Hall corruption that included the Hired Truck, city hiring and minority contracting scandals.
On Monday Roberson added yet another high-ranking government job to his dizzying resume, courtesy of Mayor-elect Brandon Johnson.
Roberson will serve as chief operating officer under Johnson and newly appointed chief-of-staff Rich Guidice.
Like Guidice, Roberson is a Daley alum who knows city government. He also worked at the Chicago Housing Authority and Chicago Park District and spent the last six years holding a series of top jobs under Cook County Board President Toni Preckwinkle, one of Johnson’s political patrons and most powerful supporters.
Chicago never had a chief operating officer until 2011. That’s when then-Mayor Rahm Emanuel created the role and filled it with the Lisa Schrader, the savvy, respected and tough-as-nails woman who went on to become his chief of staff.
Her replacement as chief operating officer, Joe Deal, followed the same path.
The chief operating officer’s job is viewed as critically important to riding herd over city departments and coordinating work across multiple city departments and city agencies.
Without a seasoned hand on the wheel, fiefdoms in those departments and agencies can work at cross purposes with dramatic consequences, as evidenced by the bureaucratic breakdowns that culminated in 2003 with both the E2 nightclub disaster and the Lincoln Park porch collapse.
Mayor Lori Lightfoot’s chief operating officer was Paul Goodrich, a banker and consultant with no experience in city government.
Johnson has chosen a different route.
He has paired Guidice with another person who knows a ton about city government, having served in so many top jobs himself. That experience is expected to prove critical for Johnson, who lacks both executive and city government experience.
Jason Lee, a senior adviser to Johnson’s transition team, said Roberson’s vast government experience and Air Force background made him a natural choice.
“Mr. Roberson has got very keen attention to detail. He’s very process-oriented. ... He’ll be a good manager of various processes that have to happen in the city and will be a complement to our team in that sense,” Lee told the Sun-Times.
“We want to transform city government. But the foundation of transforming city government is to make sure that the government we have now can work to serve the people of Chicago. So, we’re bringing in people who have a transformative vision, but also have the chops to make sure that the city runs currently on Day One.”
A Cook County commissioner, Johnson was quoted in a news release as saying he has “seen firsthand” Roberson’s “ability to execute strategic initiatives and build consensus from a variety of stakeholders.”
Roberson’s LinkedIn profile lists 17 jobs over 26 years, most of them in government. It even includes 18 months as chief of staff to 17th Ward Ald. David Moore.
Under Daley, Roberson was one of City Hall’s fastest rising stars in a whirlwind career, with stints as Park District purchasing manager; assistant to the mayor; chief of development for the CHA; commissioner of Sewers, Buildings and Aviation; and executive director of Construction and Permits.
But in 2005, Roberson became the 15th Daley Cabinet member to leave or be shown the door in a monthslong housecleaning triggered by the Hired Truck, city hiring and minority contracting scandals.
At the time, both Daley and Roberson insisted the resignation was voluntary and had nothing to do with Roberson being among 30 current or former government officials cooperating in the investigation of what federal prosecutors called a “massive fraud” in city hiring.
“He wasn’t frozen out or frozen in,” Daley said then.
Roberson said then that his relationship with Daley “didn’t change at all” after the list of cooperating witnesses circulated at City Hall.
“I don’t know who it may have been uncomfortable for. It wasn’t uncomfortable for me. I came to work every day. You can’t freeze out the airport or the person who runs the airport. It’s too critical to our economy,” he said then.
During 19 months as aviation commissioner, Roberson pushed through a controversial airport Wi-Fi contract and was forced to find replacements for several concessionaires accused of minority contract fraud.
His brusque management style offended at least one top deputy.
“When I articulate my expectations, I do it in a way I’m sure they understand and know they have to deliver results,” he said then. “I don’t make apologies for that. I do that with everybody.”
He also stirred controversy by promising to clean the toilets himself and privatizing custodial services at some O’Hare terminals.
“I wanted the bathrooms to be cleaner, and I can honestly say that our facilities are much cleaner and much better than when I came in,” Roberson said then.
As sewers boss, Roberson was in the eye of the storm surrounding Chicago’s $75 million rainblocker system used to regulate stormwater runoff into sewers. He was also on the hot seat for a gas line rupture caused by a city construction crew that left thousands of Southwest Side residents without heat.
As buildings commissioner, he declared war on his own department’s bureaucracy with a plan to streamline the city’s much-maligned permitting process.
