The political landscape in the Village of Dolton grew more turbulent as Mayor Tiffany Henyard terminated Keith Freeman, her village administrator and senior advisor at Thornton Township, amid allegations and legal entanglements; this move has stirred controversy and debate among local trustees concerning its legality and potential ramifications.

According to The Chicago Tribune, the dismissal was announced by Mayor Henyard during a public meeting, the trustees stayed silent, not supporting the action which led to questions about the mayor's authority to unilaterally fire Freeman because the board is typically responsible for voting on such employment decisions, Trustee Jason House explaining they were advised by their lawyers to remain quiet during the meeting and expressing concern over the possibility of a lawsuit stemming from the firing. Alongside this, the board made the difficult choice to lay off a handful of village employees in what Trustee Brittney Norwood described as the village "bleeding," a decision Mayor Henyard condemned as "political retaliation."

As detailed by WGN Investigates, Freeman's dismissal appears in the context of an ongoing federal investigation into Mayor Henyard's administration; Freeman, who had previously been given a written warning for absenteeism, ultimately did not submit required paperwork for a leave of absence related to family medical care and was later provided with an undisclosed stipend despite his termination, reports also indicate Henyard's management style has been under scrutiny, with the FBI serving subpoenas as part of their investigation. Freeman has submitted a plea of "not guilty" in response to bankruptcy fraud charges. Mayor Henyard did not comment on his employment status despite multiple inquiries.