Tiffany Henyard’s top aide fired

COOK COUNTY, Ill. — Embattled south suburban politician Tiffany Henyard has fired her top aide in at least one of the governments she runs. It comes as speculation has swirled about whether federal prosecutors are pressuring Keith Freeman into cooperating in their ongoing investigation of Henyard’s leadership.

Keith Freeman served as Henyard’s senior advisor in Thornton Township and village administrator in Dolton. Records obtained by WGN Investigates show Freeman was fired from the township job on July 9. Freeman denied being fired and denied cooperating with federal investigators in a text message to WGN Investigates.

However, human resource records obtained via a Freedom of Information Act request show zero hours worked by Freeman for much of the month of June and into July. He received a written warning about chronic absenteeism on June 14 with an unidentified administrator writing: “I’m asking for better communication of [your] whereabouts and more time spent at the Township.”

Henyard has frequently blurred the lines of the two governments she runs with employees such as Freeman tasked with completing work for both Dolton and Thornton Township. The FBI served wide-ranging subpoenas targeting Henyard and her allies in April, days after prosecutors charged Freeman with bankruptcy fraud for failing to report his income from Dolton. Still, Henyard kept Freeman on both government payrolls … until now.

Emails obtained by WGN Investigates show Henyard’s other top lieutenants in Thornton Township building their own case to fire Freeman. Freeman emailed an administrator requesting a leave of absence to care for an ill family member on June 21. The HR manager responded by providing Freeman with Family and Medical Leave Act paperwork and a deadline to apply by July 6. A subsequent message from the township’s HR manager said Freeman did not return the paperwork by the deadline.

“Due to the high-ranking position that you hold at the Township, this type of misconduct cannot be tolerated,” read Freeman’s termination letter dated July 9. “Your misconduct is a detriment to the smooth functioning of the Township’s operations.” Despite the termination, village financial officer Robert Hunt granted Freeman an undisclosed monthly stipend in July.

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WGN Investigates has spent more than a year documenting Henyard’s self-promotion and lavish spending of government money and resources on everything from travel to unregistered cancer charity in her name.

Freeman is apparently still technically the village administrator in Dolton, according to one trustee who said he’s heard rumblings that Freeman may lose that position as well but has seen nothing official.

“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,” said trustee Jason House, who announced he’s challenging Henyard for mayor in the 2025 election.

Freeman plead “not guilty” to the bankruptcy fraud charge. Henyard’s publicist did not respond to multiple requests for a comment about Freeman’s employment status.

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