The city of Chicago has a new reason to shake its collective head at City Hall. Mayor Brandon Johnson’s budget director, Annette Guzman, is stepping down. She was the person in charge of explaining how the city would spend your tax dollars, and she’s leaving at arguably the most critical financial moment of the mayor’s entire time in office. This isn’t just one person quitting.
It’s the latest crack in an administration that keeps losing its top money people. Over the last several months, the city has seen the chief financial officer leave, the acting CFO leave, and now the budget director walks out the door. The timing says everything. Chicago is staring down another massive budget deficit.
The city leaders who remain will have to decide whether to cut services, raise taxes, or scramble for some other way to close a hole that never seems to close. Every one of those choices affects how the city runs. And with a mayoral election just months away, the way Mayor Johnson handles the money is about to become the most talked-about issue on the campaign trail. When reporters asked the mayor about Guzman’s departure later that morning at City Hall, they wanted answers to two questions.
Why is another top financial official leaving? And how does the city plan to tackle yet another enormous budget shortfall? But looking at this from a bigger picture, you notice a pattern. This mayor has been in office for less than three years, and the turnover in his administration has been relentless.
People come, people go, that’s normal in politics. But the way this particular house has been cleaned out isn’t normal. The mayor himself said it clearly. If you aren’t with him and his plans, you have to go.
He made that statement from a pulpit at New Covenant Missionary Baptist Church, and the room was flooded with applause. It was a warning. And the exits started happening almost immediately. The Aviation Commissioner, Jamie Rhee, announced her retirement.
She had led O’Hare Airport through major construction plans and served the city for decades. The head of the Office of Emergency Management and Communications, Jose Toledo, transitioned out of his role. And the chief administrator of the Civilian Office of Police Accountability, Andrea Kersten, resigned after four years overseeing police misconduct investigations. She didn’t hide her feelings about the state of things.
She said morale in that building was the lowest she’d ever seen it. While that exodus was happening, the mayor was holding tight to his old friend, Clinée Headspeth. He hand-picked her to run the Department of Cultural Affairs and Special Events, the office that puts on Taste of Chicago and Blues Fest. She was a longtime friend of his, and he gave her one of the most visible jobs in the city.
Almost immediately, there were problems. More than 100 artists signed a letter expressing concern about her leadership. Then, an open records request revealed a former employee had filed a complaint. That complaint said Headspeth made humiliating and demoralizing comments about their culture, even asking an employee to wear traditional cultural clothes and put on a thick accent in council chambers for a hearing.
The worker said Headspeth told them to make it hard to understand them, as if that were a joke. The investigation found HR violations. Headspeth was accused of age-based harassment, telling an employee to make sure they didn’t have gray hair when going to the fifth floor of City Hall, where the mayor’s office sits. She was accused of making comments about an employee’s sexual orientation and disregarding their preferred pronouns.
She reportedly talked about her own sex life and asked an employee about their sexual preferences, even asking if they would have an affair with a married person. When asked about these allegations, Headspeth called the person a disgruntled employee. After HR found she violated the Equal Employment Opportunity Policy, she resigned less than two weeks later. During her tenure, 29 employees left that department, including seven deputy commissioners.
She is now on the city’s do-not-hire list. So the mayor fired or pushed out many people, but the person he held onto through all of those accusations was his own friend. And then there’s Jason Lee. Jason Lee is the mayor’s senior advisor and close confidant.
Two years ago, Alderman Bill Conway filed a complaint with the Inspector General alleging that Lee tried to extort him in exchange for a vote. Conway said Lee pulled him into a coat room and made a direct offer. If Conway voted to raise the real estate transfer tax on working families and raise the tip credit, the city would help clean out an encampment and a viaduct in his ward. When Conway refused, the cleanout was cancelled.
The Inspector General’s office investigated. They found that city employees are obligated by law to cooperate with their office. They said the subject of this particular investigation, Jason Lee, didn’t cooperate. They recommended Lee be terminated and placed on the no-hire list.
Lee still works at City Hall, and he claims he tried to cooperate multiple times, but that the OIG rejected his participation with private counsel. The Inspector General wasn’t convinced. She compared it to getting pulled over for speeding and telling the officer you meant to slow down before you got there. The mayor’s office backed Lee in their public statement.
The Inspector General pointed out that when other city departments received termination recommendations, those departments agreed and fired the people. But the mayor’s office was the only agency that accepted a recommendation and then refused to act on it. So the question is simple. The budget director walks away, the financial team is hollowed out, the city faces another massive deficit, and the mayor kept the one man who was credibly accused of trying to extort an alderman in a coat closet.
Will Guzman’s departure change anything? Or will he just find someone else to come in and explain why the city’s budget can never be balanced, why there’s never enough money for what needs to be paid, and why nobody is held accountable?
