Top aide to ‘worst mayor in America’ Tiffany Henyard fired

A top aide to Dolton, Illinois Mayor Tiffany Henyard has been fired from one of her jobs.

The aide, Keith Freeman, was fired in July for repeatedly failing to show up for work. Henyard is the mayor of Dolton, but she is also a supervisor in the neighboring township of Thornton, where Freeman was fired.

“Due to the high position you hold within the Township, this type of misconduct cannot be tolerated,” Thorton’s Human Resources Department wrote in its email notifying Freeman that he had been terminated. “Your misconduct is detrimental to the smooth running of the Township’s operations.”

Freeman worked as Henyard’s chief assessor in Thornton Township and as a town administrator in Dolton. Payroll records indicate he still works in Dolton.

“There appears to be a rift between Tiffany and Keith, but nothing has come out of the mayor’s office saying he is fired,” said Trustee Jason House, who has announced he will challenge Henyard for mayor in the 2025 election.

According to the Chicago TribuneIn June, Freeman received a written warning about his behavior. He was told he needed “better communications about (his) whereabouts and spending more time at the township.” Township records also show he worked just 46 hours in the entire month of June, including several weeks when he hardly worked at all.

Henyard has blurred the lines between the two cities he runs, with his employees often performing work assignments for each city.

He is also under federal scrutiny for lavishly spending city money on vacations, including one to Las Vegas where an employee claimed she was sexually assaulted by a co-worker and then fired for speaking out. Multiple lawsuits have also been filed against Henyard and Freeman for unlawful retaliation against employees.

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“They say you are the worst mayor in America. I agree,” said one Dolton resident at a meeting after the Las Vegas trip. The trip cost taxpayers tens of thousands of dollars.

Freeman is also in legal trouble after being charged with bankruptcy fraud for making false statements in a bankruptcy petition he filed earlier this year to conceal his assets and sources of income, according to a federal indictment.