The Rise and Fall of Dolton Mayor Tiffany Henyard: From Scandal, To FBI Probes, and a $99 Tell-All Book, How She Went from ‘Super Mayor’ to a Legal Lightning Rod

For a brief moment, Tiffany Henyard was the rising star of Illinois politics—elected mayor of Dolton and later supervisor of Thornton Township, she called herself Dolton’s “super mayor, and wielded considerable influence. But in the years since her 2021 victory, Henyard’s reputation has become synonymous with controversy, her story has shifted dramatically—from being celebrated as a trailblazer to facing federal probes, civil lawsuits, public outrage, and a self-published memoir with a staggering price tag. The embattled ex-mayor is now forced to defend her legacy in court, on social media, and on bookstore shelves. Here’s the full story of Dolton Mayor Tiffany Henyard’s fall from grace, the courtroom drama that followed, and the explosive revelations still to come.

Who Is Tiffany Henyard?

Tiffany Henyard, former Dolton Mayor.
Source: Kfreemantwp via Wikimedia

Before controversy and courtrooms overshadowed her name, Tiffany Henyard was a young, ambitious politician who captured the attention of the residents of Dolton. At just 41, she made history as the first female mayor of Dolton and later became Thornton Township’s supervisor. Henyard embraced the title “super mayor,” a nickname that reflected her dual leadership roles and her promise to revitalise the community.

However, behind the public image of success, questions about financial mismanagement and governance began to surface slowly. Over time, allegations mounted, leading to FBI subpoenas, mounting deficits in village accounts, and public clashes with trustees.

Why did Tiffany Henyard plead the Fifth in a FOIA battle?

In May 2025, Henyard walked into a Chicago courtroom to face a civil lawsuit filed by Edgar County Watchdogs seeking public records under the Freedom of Information Act. Subpoenaed to testify, the former mayor invoked her Fifth Amendment right 47 times, declining to answer questions about missing documents and her financial disclosures.

Her attorney, Beau Brindley, told WGN-TV that legal advice drove Henyard’s decision: “Anybody smart and reasonable… is going to protect themselves under these circumstances.” Yet, Judge Kate Moreland had already found Henyard in contempt for failing to hand over the requested paperwork, imposing a $1,000 daily fine until compliance was achieved.

Despite the order, Henyard’s team insisted she no longer possessed the documents—claiming they were lost or never existed—and planned to file a sworn affidavit in lieu of physical records. The court’s struggle to extract basic expense reports laid bare longstanding concerns over transparency during her tenure.

“Standing on Business”: A $99 Tell-All

In the midst of mounting legal and financial scrutiny, Henyard pivoted toward publishing. In mid-2025, she announced a self-published autobiography titled “Standing on Business.”

The book—reportedly the first in a three-part series—is priced at $99. On social media, Henyard promoted it with the promise that “the real story is coming,” describing her journey as “from mommy moves to making history.”

Public reaction has been harsh. Residents flooded Dolton Politics forums, criticising the book’s high price and questioning Henyard’s motives. “Michelle Obama’s bestseller was cheaper than this mess,” one commenter wrote.

Despite the criticism, Henyard has continued promoting the memoir as an unfiltered account of her time in office and her battles with political opponents.

Public Clashes and Viral Boardroom Fight

Dolton Mayor Tiffany Henyard vetoed a resolution aimed at investigating her spending following allegations that she misused taxpayer money for herself.
Source: WGN News

The chaos in Dolton wasn’t limited to financial scandals. Henyard’s leadership often turned confrontational during public meetings. One infamous incident, captured in a viral video, showed activist Jedidiah Brown calling Henyard derogatory names and accusing her of “sleeping her way to the top.”

The exchange escalated when Henyard’s boyfriend, Kamal Woods—who also managed Thornton Township’s at-risk youth program—physically confronted Brown. Security intervened as the two exchanged punches. Witnesses described a scene “scarier and more horrible” than any the township had seen. No arrests were made, but the incident underscored deep divisions in Dolton politics—divisions fueled by questions over township spending, at-risk youth programming, and allegations that Henyard’s inner circle controlled lucrative contracts.

The fight highlighted the deep divisions within the community and further fueled demands for independent investigations into Henyard’s spending and leadership style.

What did Lori Lightfoot’s independent probe uncover?

Tasked by Dolton trustees, former Chicago Mayor Lori Lightfoot released a 73-page investigation in July 2024 detailing “blatant disregard” for village purchasing rules under Henyard’s leadership . Key findings included:

• Systematic efforts as early as late 2021 to hide the village’s true financial condition from trustees and the public.

• Trustees were cut off from regular budget reports by March 2022, leading to a $5.6 million cash reserve plummeting to a $3.6 million deficit by May 2024.

• $779,000 in suspect credit-card charges in 2023, including $50,000 on ice rink supplies never approved under policy.

• Vendor payments are overdue by over $5 million, as insurers have even refused to cover Henyard’s liability risks.

Lightfoot’s report recommended sweeping governance reforms—only to be decried by Henyard’s lawyer as the work of “a failed mayor seeking limelight.” Yet, within months, trustees had cut the deficit to $2.4 million, signalling the probe’s tangible impact on Dolton’s finances.

A Stunning Primary Loss

Dolton Trustee Jason House claps after winning the mayoral primary against incumbent Tiffany Henyard, speaks to supporters at an election night party on Tuesday, Feb. 25, 2025.
Source: Vincent Alban/The Sun-Times

While Henyard had survived previous political battles, voters ultimately delivered the final blow. In early 2025, she suffered a resounding defeat in the Democratic primary to Jason House, who was sworn in as Dolton’s new mayor in May.

On the same day as her election loss, federal authorities intensified their probe, issuing additional subpoenas related to land development projects allegedly connected to Henyard’s boyfriend.

Where does Tiffany Henyard stand as she eyes a comeback?

After losing the 2025 Democratic primary—her second electoral defeat—Henyard still holds her supervisor post but faces an active FBI criminal investigation into alleged misuse of township and village funds. Multiple subpoenas sought travel records, credit-card statements, and expense reimbursements tied to at-risk youth programs and development projects connected to her boyfriend.

With weekend oral arguments in the FOIA contempt hearing pending and a tell-all book launch looming, Henyard’s next moves will determine whether she can shed her “Dictator of Dolton” designation or forever remain an exemplary story of small-town power gone wrong.

Where Does Tiffany Henyard Stand Today?

As of July 2025, Tiffany Henyard is no longer in public office, replaced by new leadership aiming to restore Dolton’s financial stability. The federal investigation remains active, with no public resolution having been announced yet.

Her legacy is complex: a groundbreaking female leader whose administration spiralled into financial chaos, public scandals, and federal scrutiny. Whether her upcoming memoir reshapes public opinion or further divides the community remains to be seen.

FAQs

Who is Tiffany Henyard? A Democrat elected mayor of Dolton in 2021 and Thornton Township supervisor, nicknamed “super mayor” before being unseated in the 2025 primary.

Why did she plead the Fifth? Henyard refused to testify regarding missing FOIA documents, invoking the Fifth Amendment on legal advice amid an ongoing federal probe and civil lawsuit .

What is Standing on Business? Henyard’s self-published memoir—priced at $99—promises to reveal her side of the story, including scandal, politics, and personal struggles.