“Y’all say Martin Luther King had a dream, but guess what? I am the dream.”

—Tiffany Henyard, January 4, 2024


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“You all forget that I’m the leader. They want to hear from the mayor, ya’ll ain’t learned that yet,” yelled Tiffany Henyard at a public meeting on February 5th. “The mayor, not the trustees who don’t do nothing. They only run their mouth. You all don’t do no work, no work!”

It’s Black History Month in Dolton, Illinois, a small village of around 20,000 in the Chicago suburbs, and the mayor is having none of it.

“You all should be ashamed at yourselves because you are all black,” she went on, yelling at Dolton Trustees. “You are all black! And you all sitting up here beating and attacking a black woman that’s in power. You should all be ashamed of yourselves.”

Two days later, she announced on Facebook that she would be giving away $1 million to commemorate Black History Month:

Local press in Chicago reported residents were “confused,” and journalists’ calls to Henyard’s office for clarification went unanswered. As Tiffany later revealed on Facebook Live, the million-dollar giveaway is actually a program that allows renters and homeowners to receive up to $3,000 of housing assistance per applicant. The money Henyard wants to use for the giveaway will come from a General Assistance Fund administered by Thornton Township — where Henyard serves as supervisor, in addition to being Dolton’s mayor.

Self-promotion is Henyard’s MO. Her face dots the landscape of Chicago’s south suburbs on taxpayer-funded billboards. You know it’s her face because her name is also on the billboards, at the top, above advertisements for various city services. In some of the ads, she’s pointing at the commuters below; in others, she’s making the “call me” gesture. In all the ads, though, she’s wearing a low-cut yellow blazer that, to her credit, is definitely her color. What’s more, a year ago, the self-proclaimed “Super-Mayor” and “Most Powerful Woman in the Southland of Chicago” released a music video, filmed with city employees at taxpayer expense, lip-syncing a song that’s not her own. The Southland Journal posted the video with the following description, which is funnier than anything I could come up with:

Mayor Tiffany Henyard has been under constant heat for allegations of corruption and flaunting the law in Dolton and Thornton Township. However she claims innocence and keeps a positive vibe which is displayed in her latest music video.

The cartoonish nature of those corruption allegations has made me obsessed with this woman in a way that I have not been with any politician since George Santos (who I wrote about here) was unceremoniously expelled from the House of Representatives by his snake colleagues. Since Henyard was elected Mayor of Dolton in February 2021, she’s been plagued by controversies — each more ridiculous than the last — but nothing seems to faze her. She’s actually accumulated even more political power, becoming Supervisor of Thornton Township (a broader municipality encompassing the village of Dolton) in March 2022 in what local press called “a stunning conclusion to a process that has been marked by frustration and confusion.”

The controversies started early, in 2021 when Henyard personally hired two people without the required advice or consent of city trustees. The first hire was Dorothy Brown, a former County Circuit Court Clerk who had recently stepped down after two decades of scandals and federal investigations that saw several of Brown’s underlings carried off to prison. Henyard refers to Brown as her “mentor and godmother.” The second was Lavelle Redmond, a convicted gang rapist who had volunteered on Henyard’s mayoral campaign. He was hired as a code inspector, which stunned residents, alarmed that a convicted sex offender would be tasked with inspecting their homes and businesses which means entering homes and businesses where there are children and other vulnerable people present). For this, Henyard was censured by the board of trustees in Dolton, but Redmond wasn’t fired — at least not immediately. He was placed in a “Second Chance Program” after a representative for Henyard said they had known nothing about his criminal history, though that was contradicted by an interview that Redmond gave to Daily Southtown’s Ted Slowik — the reporter he was fired for talking to.

“Every single resident,” began Tiffany Henyard in a Dolton meeting last year, pausing for the chorus of Rhianna’s Bitch Better Have My Money, “Pay me what you owe me,” Henyard said.

Pay me whatchu owe me, Rhianna repeated from the speakers in seeming affirmation.

“Thank you DJ,” said Tiffany, who had come to the meeting dressed as Wesley Snipes's character in the 1991 movie New Jack City.

And pay the residents of Dalton and Thornton township have. Not just for the billboards, and the music video, but also for expenses related to the “Tiffany Henyard Cares Foundation,” a dubious breast cancer charity she started in 2022, and has greatly promoted since. The mayor and township supervisor led a “Tiffany Henyard Cares” walk from Dalton to Springfield in 2022 to promote herself, it appears and spent over $10,000 on company credit cards along the route in addition to the $10,000 the town granted directly to the charity at Henyard’s behest. The charity has refused to submit required financial disclosures required by the state — even after being sent a letter from the Illinois Attorney General demanding them. Because of this, it's unclear what the granted money was used for. She also reportedly used city money to take a first-class trip to Vegas, spending more than $8,000 on hotels and hundreds at restaurants like Ruth's Chris Steak House, Hot n’ Juicy Crawfish, and Bubba Gump Shrimp Company. Henyard brought the red Bubba Gump Shrimp Company with her to the meeting in which her spending on the Vegas trip was discussed but denied any wrongdoing. When reporters asked Henyard where she stayed in Vegas and whether she gambled she replied, “Mhmm.” Later, when asked if she flew first class she replied, “Any other questions?”

In her two combined positions as Mayor of Dolton and Supervisor of Thornton Township, Henyard makes over $300,000 — the bulk of it from her supervisor position, which pays $224,000 — as long as she holds the position, anyway. Late last year, she successfully lobbied the Township to pass an ordinance that would cut the position’s pay to $25,000, but only if Henyard loses the election. Her haters — and their lawyers – have described it as “illegal in so many ways,” but thus far Henyard has been able to skirt the consequences of her various alleged crimes and misdeeds. She was recalled by voters in 2022 by a relatively small margin considering the situation (56%), but got the results thrown out on a technicality.

She’s Teflon-Tiff, a charismatic authoritarian whose relentless pursuit of power seems unstoppable — an American Caesar who hasn’t had her Ides of March moment yet. She’s even amassed something of a Praetorian guard, pulling officers off the street to serve in her ever-expanding personal security detail. Earlier this week, the former Dolton Police Chief — who was fired by Henyard late last year because, allegedly, his wife is friendly with people Henyard perceives as political opponents — told Fox 32 Chicago that Henyard used the police force as a private security and chauffeur service, which cost taxpayers thousands and left the force unable to adequately fight crime. This seems to confirm an earlier report by Fox 32 which found that taxpayers had forked over “hundreds of thousands” worth of overtime payments to officers assigned to Henyard’s security detail.

The only thing more cartoonish than Tiffany Henyard’s antics is the idea that Nancy Pelosi just so happens to be one of history’s greatest day traders, the Warren Buffett of her time. There’s something strangely honest about obvious, small-scale, even flagrant corruption. I assume that politicians are wasting my money and the most cruel thing they can do is bore me in the process. Long live comedy, and long live Tiffany Henyard, America’s mayor, the only politician who has the courage to be as corrupt in public as the rest of them are in private.

– River Page