A controversial Illinois lawmaker once dubbed 'America's worst mayor' for a string of scandals has seen her fortunes dramatically improve since defecting to the Republican Party. Tiffany Henyard, 42, the former mayor of Dalton, Illinois, won in court this week against her former landlord as a judge ruled that she did not owe almost $10,000 in unpaid rent. The courtroom victory came weeks after Henyard won a comeback election in the Republican primaries for a seat on the Fulton County Board of Commissioners in Georgia. The win marked a stunning turnaround for Henyard after she was unceremoniously booted from office last year, losing her re–election by a landslide as voters had enough of her scandal–plagued tenure.

Despite her reputation for controversy, which included allegations that she mismanaged millions of dollars and got into physical fights with activists, Henyard plotted a return to public office starting in the spring. She switched from Democrat to Republican in March, saying at the time that she 'can't stand by the things that I've seen within the (Democratic) Party', while the GOP 'represents faith, family, future growth and economic policy.' Henyard dubbed her comeback run 'Project Phoenix', and won the Republican nomination for the election last month. But even though she won her primary in Georgia, critics say Henyard faces an uphill struggle to win the general election in a heavily Democratic district. 

While Hayward's comeback campaign may end without a return to public office, she also scored a victory back in Illinois in her dispute with a former landlord. Henyard and her boyfriend, Kamal Woods, were accused in 2024 of being almost $10,000 behind on rent and other costs at their home in the in the 14600 block of Harvard Street of Dolton. The case added to a number of legal issues and investigations facing the then–mayor. This week, Judge George Canellis of the Cook County Circuit Court ruled that Henyard's name was not properly signed on the lease, allowing her to skirt the allegations, according to the Chicago Tribune. However, the judge ruled that Woods owed the landlord, Genetta Hull, more than $7,000, per the outlet. Henyard was also granted over $1000 in backpay from the landlord to offset the costs of an ID protection service, plus $500 in attorney fees.

Judge Canellis said the relationship between Henyard and her former landlord had 'become contentious,' as he sanctioned Hull for allegedly publishing Henyard's Social Security number. 'Henyard is a public figure and has garnered a tremendous amount of attention from the public both locally and nationally,' Judge Canellis said. He added: 'The court does find this to be a very serious breach of Henyard's privacy.' The courtroom victory comes after Henyard endured a torrid time as Mayor of Dalton, about 25 miles south of Chicago. She was accused of mismanaging millions of dollars and sinking the village into debt during her tenure. Last January, an independent investigation found Henyard, then a Democrat, allegedly mismanaged millions of dollars worth of taxpayer funds.

Former Chicago Mayor Lori Lightfoot revealed the findings of her independent investigation into the alleged wrongdoings of Henyard. 'At least as early as late 2021, there was a concerted, systematic effort on behalf of Mayor Henyard and others in her administration to hide the true financial condition of the Village of Dolton from the trustees and from members of the public,' Lightfoot said, per FOX32. Lightfoot's 73–page report said $779,638 had been charged to town credit cards in 2023, with slim tracking of the actual expenses.

At least six government credit cards were used to pay for trips that Henyard took to Las Vegas in May 2022 and May 2023, per the report. From 2021 through June 2024, credit cards were used for over $171,000 in travel–related expenses, including airfare, baggage fees, hotels, meals and rental cars. The report into Henyard's conduct in office also revealed that over $50,000 was spent at local restaurants. Purchases were also made at well–known brands like Dick's Sporting Goods, Best Buy, Wayfair, Walgreens, Apple and Walmart. As a result of this spending frenzy, allegedly done by Henyard, the Dolton Board of Trustees banned her from using town credit cards in August 2024.

The report also alleged that Dolton had a budget surplus of $5.61 million in April 2022 that quickly shrank to a $3.65 million deficit by May 2024. Lightfoot said Dolton received some $3 million in payments from the American Rescue Plan, a COVID–19 stimulus bill signed into law by former President Joe Biden in 2021. Henyard previously visited the White House as part of the US Conference of Mayors Annual Winter Meeting in 2024. During the trip, she live–streamed part of the visit, which included her meeting with Biden. The Daily Mail has reached out to Henyard, her boyfriend Woods and her former landlord Hull for comment.