My neighbor knocked on my door last week, and she was holding her phone up with this insane look on her face. “Honey, you’ve got to look at this,” she said. She’d been looking at a Facebook post, someone selling a book for ninety-nine bucks. And it was not just any book, but a tell-all from Tiffany Henyard, the former mayor who’s been all over the news.
I thought she was joking. Who pays that much for a book nobody wants? Yet here we are in August 2025, and that’s precisely what’s taking place.
Who Is Tiffany Henyard Anyway?
If you live anywhere near Chicago, it’s a name you’ve likely heard. Tiffany Henyard declared herself the “most powerful woman in the Southland of Chicago.” She had been elected mayor of Dolton, Illinois, a small suburb with significant problems. She also held another position, as Thornton Township supervisor. Two government positions at once. Not bad, right?
Wrong. Really, really wrong.
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The Rise and Fall
Henyard made headlines for all the wrong reasons. She threw around taxpayer money like confetti at a parade. Security measures that cost more than other people’s homes. Trips that were unrelated to city business. The whole thing was bananas.
I recall watching her on the news last year, discussing how she was making history. She had this swagger that was either inspiring or disturbing, depending on how you looked at it. Turns out it was mostly terrifying.
Lawsuits from every direction were filed against the woman. There have been violations of the Freedom of Information Act. There are questions about where the money went. The FBI started sniffing around. Things got messy fast.
Election Day Reality Check
Everything fell apart in February 2025. Henyard lost her mayoral race in a landslide, despite her prediction that she’d win convincingly. Her former ally, Jason Hous, wiped her out with nearly 88% of the vote. That’s not losing; that’s getting your clock cleaned.
Can you imagine? You wake up on election morning, confident that you will dominate, but by the end of the day, you find yourself packing up your office. The message from the electorate was loud and clear.
But wait, there’s more. She also tried and failed to win the Democratic nomination for township supervisor, losing out in a caucus fight to State Senator Napoleon Harris. Two losses in one year. Ouch.
Court Drama and Legal Troubles
But the legal stuff kept piling up long after she lost. In May 2025, she was cited for contempt of court for violating the Freedom of Information Act. She was forced to go to court, and she actually pleaded the Fifth Amendment. That is not a good sign in local politics.
My cousin is in government finance, and she said FOIA violations are no joke. When someone won’t hand over public records, it usually means they’re hiding something big. The contempt count was later dismissed, but Henyard may still face fines and lawyer fees.
The $99 Book Nobody Asked For
Here is where it gets really wild. Henyard is currently selling a book called “Standing on Business” for $99 as a pre-order. Ninety-nine dollars! For a book! From someone who just lost two elections and got slapped with a bunch of lawsuits!
According to the description, the book promises to tell about “real-life political warfare, betrayal, and the unwavering ambition to rise above it all.” Her lawyer maintains all her travails were simply a “smear campaign.”
Listen, I am all for people sharing their version of the story. But a hundred bucks for it? That takes some serious nerve. For that price, you could buy three ordinary books. Or a nice dinner. Or gas for your car for the next two weeks.
What’s Really Going On Here?
This whole situation reminds me of watching a train wreck in slow motion. You want to avert your eyes, but you cannot. Henyard began as a political star on the rise and is now selling overpriced books and avoiding legal tangles.
The crazy part is how she still presents herself. Her Facebook page continues to describe her as “the most powerful woman in the southland of Chicago.” Even after losing everything! That’s either amazing confidence or total denial. Maybe both.
I’ve watched politicians fall from grace before, but something feels different this time. The majority of them simply retire in peace and write reasonably priced memoirs. Not Henyard. She is doubling down and charging premium prices and acting like she still runs the show.
Lessons from the Mess
What can ordinary folks learn from this entire disaster? First, get into local politics. These local races matter more than you might realize. The things your mayor controls are your property taxes, your police department, and your garbage pickup. If they are throwing around money like drunken sailors, you are the one who pays.
Second, anytime someone describes themselves as the “most powerful” anything, it tends to be a red flag. The powerful don’t have to tell you they’re powerful. They just are.
Third, accountability matters. Henyard might be selling her side of the story for $99, but the voters already gave their verdict for free. Sometimes the simplest explanation is the right one.
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What Happens Next?
Where this story goes from here, no one knows. Will people actually buy her book? Will she get into more legal trouble? Will she ultimately try to run for something else?
One thing is for sure: Tiffany Henyard is not going down without a fight. Whether that’s admirable perseverance or delusional denial is, of course, a matter of perspective.
For now, she’s gone from leading a city to selling books on social media. That’s quite a career change. Makes you wonder what she will do next.
The whole mess has the feel of a political soap opera. You couldn’t make this up if you tried.