Tiffany Henyard Saga: Federal Probe Deepens, focus on Ex-Mayor’s Boyfriend

Dolton, IL – March 08, 2025 – The saga surrounding Tiffany Henyard, the controversial former mayor of Dolton, Illinois, continues to unfold with fresh developments that have thrust her and her boyfriend, Kamal Woods, into the spotlight once again. Henyard, once dubbed the “Dolton Dictator” for her brash leadership style, was ousted from office in a landslide primary defeat on February 25, 2025. Now, federal authorities have intensified their investigation, issuing a subpoena targeting records linked to a land development project allegedly tied to Woods, signaling that Henyard’s troubles may be far from over.

A Crushing Electoral Defeat

Tiffany Henyard’s political downfall came swiftly and decisively. In the Democratic primary for Dolton mayor, she garnered just 536 votes—roughly 12%—against Village Trustee Jason House, who swept to victory with 3,896 votes, or 88%, according to unofficial results from the Cook County Clerk’s Office. The election, held on February 25, marked a stunning rebuke of Henyard’s tenure, which had been plagued by allegations of financial mismanagement, retaliation against critics, and a lavish lifestyle funded by public money. “This does not represent Dolton,” House told CBS Chicago, reflecting the sentiment of a community eager to move past the chaos of Henyard’s reign (Yahoo News, “Illinois 'Super Mayor' Tiffany Henyard loses by a landslide in bid for reelection,” Feb. 26, 2025).

Henyard, who also served as Thornton Township supervisor, skipped the first Dolton Village Board meeting post-defeat on March 3, 2025. In her absence, the board took decisive action, approving collective bargaining agreements with firefighters and settling lawsuits that had lingered under her administration. They also overrode a veto from Henyard to issue a liquor license to Pablo’s Cafe and Bar, a move upheld by court order after she allegedly refused to comply (Chicago Tribune, “Tiffany Henyard absent from Dolton Village Board meeting after primary defeat,” Mar. 4, 2025).

Federal Subpoena Targets Boyfriend Kamal Woods

The same day Henyard lost the primary, February 25, the Village of Dolton received a federal subpoena from the FBI, demanding records related to a Lincoln Avenue development project allegedly once owned by Kamal Woods, Henyard’s boyfriend. The subpoena, obtained by ABC7 Chicago, seeks documents dating back to 2014, including citations, code violations, and communications between property owners, tenants, and village personnel tied to the project. Authorities have also requested testimony on March 17 at the Dirksen Federal Building in Chicago (ABC7 Chicago, “FBI serves village of Dolton subpoena involving Mayor Tiffany Henyard's boyfriend, Kamal Woods, officials say,” Feb. 28, 2025).

This latest move builds on an ongoing federal investigation into Henyard herself. Previous subpoenas sought personnel files, wage and tax records, contracts, and checks from her various ventures—including a restaurant, a property management company, her political action committee, and a charity bearing her name. The New York Post reported that the feds are probing alleged money mismanagement, with the Woods subpoena suggesting a broader net cast over her inner circle (New York Post, “Feds seek records tied to ousted 'Super Mayor' Tiffany Henyard's boyfriend,” Mar. 4, 2025).

Woods, who has been a polarizing figure in the saga, was also implicated in a physical altercation at a Thornton Township meeting in January 2025. Critics Jedidiah Brown and Lavell Redmond filed federal lawsuits claiming Woods attacked them in retaliation for their outspoken criticism of Henyard, an incident allegedly sparked by Brown’s profanity-laced rant against her. Both lawsuits name Henyard, Woods, and others, alleging violations of their First Amendment rights (New York Post, “'Dolton Dictator' Tiffany Henyard, boyfriend Kamal Woods sued for attacking freedom of speech,” Feb. 19, 2025).

Henyard’s Response and Lingering Support

In the wake of her electoral loss, Henyard took to social media on February 27, addressing her followers with a message that stopped short of conceding defeat. “I am rare and truly care about my communities,” she had previously written in September 2024, a sentiment she echoed as she framed criticism as a “smear campaign” (NBC Chicago, “Tiffany Henyard shares message days after Dolton primary,” Feb. 27, 2025). Despite her ouster, some residents remain loyal. One supporter, identified only as Jessie, told the New York Post, “If any of the allegations were true, the FBI would have locked her up long ago,” reflecting a lingering divide in Dolton (New York Post, “'Dolton Dictator' Tiffany Henyard still has holdout supporters after landslide election loss,” Feb. 26, 2025).

What Lies Ahead

With Henyard’s mayoral term nearing its end and her likely loss of the Thornton Township supervisor role to Illinois State Sen. Napoleon Harris in the April 1 general election, her political career appears all but finished. Yet the federal investigation looms large. The focus on Kamal Woods raises questions about the extent of his involvement in Henyard’s alleged schemes and whether the couple’s personal and financial entanglements will lead to criminal charges. 17GEN4.com