All The Alleged Schemes, Scandals and Shenanigans That Keep This Chicago-Area 'Super Mayor' In The News

The first bombshell allegation to strike Henyard’s office came in March 2024, alleging she misused taxpayer money to fund a series of her own personal (and pricey) expenditures, per The New York Post.

In March of 2024, village trustees requested a third-party investigator to look into suspicious spending around Henyard’s trips, per the Washington Examiner. Specifically, they requested a look into a trip she took to Las Vegas with two other village trustees. A previous investigation into the trip found no wrongdoing. Yet, other trustees remain skeptical.

In response to the allegations of spending taxpayer money, the board attempted to pass a resolution to investigate her spending. However, Henyard vetoed the resolution claiming she was being personally attacked by the “boys club” that is the village board who she claimed was just trying to lead a smear campaign against her, per The New York Post.

The allegations of Henyard’s alleged lavish spending also included a claim she used $1 million for a police detail for personal security. The former police chief, who was fired by Henyard, told FOX 32 Chicago he believed she misused the funds creating protection for herself which took more officers off the street patrol to fight crime. The news outlet found the officers assigned to Henyard worked endless hours of overtime which in turn, cost taxpayers more money.

Former village trustee Valeria Stubbs, who publicly criticized the mayor, claimed she was retaliated against by Henyard. She told The New York Post Henyard repeatedly intimidated and harassed her at her home, including sending hitmen to shoot up the vehicles of two of her tenants. Stubbs alleged Henyard made allies with the police department on purpose so they’d ignore the complaints she made against the mayor.

WGN Investigates found the village of Dolton owed over $427,000 to a street-paving company for work done in 2002. On top of that, a bank threatened to repo vehicles belonging to the village including cop cars due to unpaid balances. A tree-trimming company is also owed $400,000 for work they did in 2023, the report said. For other vendors, the report found another $50,000 is owed in overdue payments. The mayor admitted in a board meeting that there’s a $2 million deficit the village is facing. However, she held a random $1 million Facebook giveaway in February of 2024 in honor of Black History Month, per FOX 32.

Henyard’s former assistant alleged she was sexually harassed by a trustee on Henyard’s board. When she told Henyard about it, the mayor responded that if the incident went public “she’d be ruined,” per NBC Chicago.

After Henyard’s former assistant reported the sexual assault claims against the trustee, she claimed the mayor promised she’d take care of it but was involuntary placed on unpaid medical leave and soon, terminated, per NBC Chicago.

Former maintenance manager Dwayne Thrash filed a lawsuit alleging in 2023, he was terminated while on vacation after refusing to cooperate in a scheme where Henyard and her assistant planned to fire an attorney and replace them with a firm preferred by the mayor’s assistant, per the Washington Examiner.

Henyard was alleged to spearhead a $200,000 payment in a no-bid, no-contract deal with a suburban construction company which has been linked to multiple corruption cases, featuring one where the owner allegedly tried to run a scheme to clear thousands in unpaid taxes from family-owned properties, per the Illinois Answers Project.

The mayor was served a subpoena last month in connection to an investigation into the village’s permitting and licensing practices, per WGN9 News. The FBI documents sought a series of financial documents including payroll, reimbursement, travel and expenses. Henyard, in particular, was accused of denying permits to those whose businesses she considers unfaithful to her. She’s denied those claims.

Henyard boasting her plans of creating the Tiffany Henyard Cares Foundation in 2022. However, upon the other allegations this year of frivolous spending, she began distancing herself from the charity claiming she doesn’t have a foundation and denied knowing anything about the Illinois Attorney General’s office banning the organization from raising any money, per the Illinois Answers Project. 

One of the people served a federal subpoena in the investigation into the sketchy construction project was Kamal Woods. According to FOX 32 and Illinois Answers Project, Woods was identified in Henyard’s divorce records as her girlfriend and was accused of earning a “highly lucrative salary” coming up to over $100,000 a year in addition to working private security for local government.

The U.S. Attorney’s Office for the Northern District of Illinois announced charges against Dolton’s senior administrator, Keith Douglas Freeman, in connection to allegations of bankruptcy fraud, underreporting income and submitting old income tax returns, per ABC 7 Chicago. Freeman’s position was questioned by Dolton’s trustees over whether Henyard hired him as an employee or on contract.

According to Illinois Answers Project, the township of Dolton was billed $17,000 for merchandise Henyard used for herself and her foundation. After a federal subpoena requested the documents related to that payment and found the invoice for the merchandise went out just one day after Henyard’s foundation was submitted to the state.