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

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

The aide, Keith Freeman, was fired in July for repeatedly not showing up to work. Henyard serves as Dolton’s mayor, but she is also the town supervisor of the neighboring township of Thornton, where Freeman was fired. 

“Due to the high-ranking position that you hold within the township, this type of misconduct cannot be tolerated,” the Human Resources Department of Thorton wrote in its email notifying Freeman he had been fired. “Your misconduct is a detriment to the smooth functioning of the township’s operations.”

Freeman was working as both Henyard’s senior adviser in Thornton Township and as village administrator in Dolton. Payroll records indicate he is still employed in Dolton. 

“There appears to be a severing of ties going on between Tiffany and Keith; but nothing from the mayor’s office has come out saying he’s terminated,” trustee Jason House, who announced he’s challenging Henyard for mayor in the 2025 election, said. 

According to the Chicago Tribune, Freeman was given a written warning about his behavior in June. He was told he needed to have “better communications of [his] whereabouts and more time spent at the township.” Records from the township also show he worked just 46 hours in the entire month of June, including several weeks with nearly zero hours.  

Henyard has blurred the line between both towns she runs with employees oftentimes doing work tasks for each town. 

She is also under federal scrutiny for lavish spending of town money on vacations, including one to Las Vegas, where an employee claimed she was sexually assaulted by a fellow employee and then fired for speaking out. Multiple lawsuits have also been filed against Henyard and Freeman for unlawful retaliation against employees. 

“They say that you’re the worst mayor in America. I agree,” one Dolton resident said at a meeting following the trip to Las Vegas. 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.