Chicago is in another budget crisis, and the mayor’s budget director, Annette Guzman, just quit. She helped draft the city’s spending plan, and now she’s walking away at one of the most critical financial moments for Mayor Brandon Johnson’s administration. Her resignation is just the latest shakeup in the mayor’s finance team. Over the past few months, several top financial leaders have left, including the CFO and the interim CFO.
The timing matters because Chicago is facing another significant budget deficit next year. City officials will have to decide whether to cut services, raise revenue, or find another way to close the gap. The political stakes are high. With the mayoral election just months away, how Johnson handles the city’s money is expected to become a major campaign issue.
He’s set to address Guzman’s departure later this morning. Reporters plan to ask him two questions: why another top financial official is leaving, and how the city plans to deal with what looks like another massive budget deficit. But this isn’t the first time Johnson’s team has seen turmoil. The mayor, whose approval rating is under 10%, has a history of pushing people out.
He once said, “If you’re not with me in my terrible plans and policies, if you don’t want to do things the way I do, then you need to leave. ” And many have left. Three more city department leaders announced their departures recently. Jamey Reilly, the aviation commissioner, retired just as O’Hare Airport begins building new terminals.
Jose Tirado, the head of the Office of Emergency Management and Communications, stepped down. And Andrea Kersten, the executive director of the Civilian Office of Police Accountability, resigned after four years of overseeing investigations into police misconduct. Morale in that building is reportedly at an all-time low. Then there’s the case of Clennett Hidsmith, the former commissioner of the Department of Cultural Affairs and Special Events, known as DCASE.
She was Johnson’s old friend, appointed in March 2024 to run the department that organizes major events like the Taste of Chicago and the Blues Festival. She resigned less than two years later, and she’s now on the city’s do-not-hire list. NBC 5 Investigates obtained documents revealing allegations of discrimination and harassment against her. A former employee complained she made “demeaning and demoralizing comments about their culture.
” She allegedly told an employee to wear “traditional cultural clothing” and speak with a heavy accent so they’d be hard to understand in the council chamber. She claimed it was just a joke. The Human Resources department found she also engaged in age-based harassment, telling an employee not to show gray hair when going to the fifth floor of City Hall where the mayor’s office is located. Other claims included making comments about an employee’s sexual orientation and ignoring their pronouns.
HR concluded she violated the city’s equal opportunity policy. During her time in office, 29 employees left DCASE, including seven deputy commissioners. Then there’s Johnson’s close friend and senior advisor, Jason Lee. Two years ago, Alderman Bill Conway filed a complaint with the Inspector General, alleging Lee tried to extort him.
Conway said Lee pulled him into a coat room and offered help with a camp in his ward in exchange for Conway’s vote to raise the real estate transfer tax and increase the gratuity credit. “Once I didn’t do those things, the cleaning of that bridge was canceled, and that was unfortunate,” Conway said. The Inspector General’s office found that Lee failed to cooperate with the investigation, which is a legal obligation for city employees. They recommended his termination and placement on the do-not-hire list.
But Lee still works at City Hall. He claims he tried to cooperate, but only after disciplinary action seemed likely did his lawyer reach out to the Inspector General. “That’s not enough,” the Inspector General said. “If you’re pulled over for speeding, you can’t tell the officer you intended to slow down before you got there.
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The mayor’s office has supported Lee. But the Inspector General noted that in other cases where they recommended termination, the departments agreed and fired the employees. This time, the mayor’s office was the only agency that didn’t follow through. So now Chicago faces another budget shortfall, another financial leader walking out, and a mayor who keeps protecting his friends while pushing out others.
Guzman’s departure may change nothing, or it may be a sign of something bigger. The city waits to see what happens next.
