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‘Dolton Dictator’ Tiffany Henyard notches legal victory a...
David Propper · 2026-06-25 · via New York Post

The wins keep coming for this self-proclaimed “super mayor.”

Ex-Illinois mayor Tiffany Henyard notched a legal victory this week after cruising to an easy win at the ballot box last month, as the “Dolton Dictator” continued her march back to relevancy — this time as a Republican.

Henyard, who’s running for office in Georgia, returned to her old stomping grounds Monday, where a Cook County judge ruled her former landlord must pay her $1,500, according to reports.

Tiffany Henyard smiling after voting, with an "I Voted Fulton Votes" sticker on her shirt.
Tiffany Henyard notched the legal win this week. Facebook / Tiffany Henyard

The judge also rejected the landlord’s argument that Henyard owed about $10,000 in unpaid rent and other costs at her Dolton home – instead demanding her boyfriend pony up more than $7,000, WLS reported.

The property owner, Genetta Hull, initially made the claims against Henyard and her beau, Kamal Woods, when she filed eviction papers in 2024, according to the Chicago Tribune.

Henyard avoided any financial pain because Judge George Canellis found the ex-Dolton village mayor and former Thornton Township supervisor did not sign leases on the home between 2012 and 2023, the newspaper reported.

Instead, Woods, a former town employee, was hit with a $7,060 judgment against him. The pot of money was connected to overdue rent and costs for repairs, the Tribune reported.

Canellis also ordered Hull to pay Henyard, a Democrat-turned-Republican, for allegedly publishing the ex-elected official’s Social Security number intentionally.

“Henyard is a public figure and has garnered a tremendous amount of attention from the public both locally and nationally,” the judge wrote, according to the Tribune. “The court does find this to be a very serious breach of Henyard’s privacy.”

Tiffany Henyard, Mayor of Dolton, Illinois, standing and holding a box of Fannie May chocolates.
Henyard is running for office in Georgia. Instagram / @tiffanyhenyard

A thousand dollars would go toward an identity theft protection service and the other $500 for legal fees.

Henyard’s time in office in the Chicago suburb was filled with zany controversy, leading residents to dub her the worst mayor in America and catching the attention of federal authorities.

After losing her re-elections in the village and town, she has since moved to Fulton County and changed party affiliation to run for a commissioner’s seat.

She ran unopposed in a GOP primary, but still cheered the inevitable win last month.