It was election night in February 2021, and results showed Tiffany Henyard on the verge of becoming Dolton’s first Black female mayor. Encouraged by the numbers, Henyard told a Daily Southtown reporter that Dolton residents were “ready for change.” “Right now, people are just sad,” she said. “They are looking for something to uplift them. That’s what I bring, a passion, transparency, accountability.” A little more than a year later, in March 2022, Henyard would take on the additional role of Thornton Township supervisor following the death of Frank Zuccarelli, who had been in that position since 1993. But not long after her election as mayor and even before her installation as supervisor of the state’s biggest township, Henyard began clashing with village trustees over spending and transparency. Her building and breaking down of intergovernmental relationships would continue in Dolton and at the township. Now she faces head winds as she seeks reelection as mayor in the February Democratic primary and tries to challenge being kept off the ballot in her run for a full term as township supervisor. Federal authorities continue to investigate her actions in both roles, issuing subpoenas for records and interviewing her associates. Dolton trustees launched an effort to recall her as mayor, resulting in 56% of voters favoring her ouster, though the process was ruled illegal by the courts. Dolton resident Dan Lee speaks Dec. 2, 2024, during a public comment period at the Dolton Village Board. (Vincent D. Johnson / for the Daily Southtown) Dan Lee, a longtime Dolton resident, has been a regular attendee at Dolton Village Board and Thornton Township meetings. Instead of the promised transparency and accountability, “she turned into a Frankenstein’s monster,” Lee said. “It’s been this ‘my way or the highway attitude.’” At a Dec. 2. Village Board meeting, Lee described Henyard and her administration as a “cancer that has been eating away at our community for nearly four years.” Henyard’s ‘dream team’ Henyard was initially seen as a reformer. A trustee for eight years, she defeated Riley Rogers, who led the village since 2013 and followed the Shaw brothers’ political influence. Rogers had been accused of misdeeds by trustees, including Henyard, who was elected to the board in 2013. In May 2019, trustees voted 5-1 vote on a resolution calling for an outside investigation into Rogers, with trustees saying they learned of “numerous improprieties concerning the mayor’s use of village funds, employees and resources.” Speaking to residents at a Village Board meeting, Rogers denied any wrongdoing, telling residents that, as mayor, “I’m not here to intentionally defraud this community or be untruthful to residents.” In February 2021, Rogers, who had suffered a stroke in January, competed in a four-person Democratic primary, garnering 30.2% of the vote to 34.5% for Henyard.  Lee, a Dolton resident since 1989, said as a trustee, Henyard was one of Riley’s chief critics. “She was calling for the same transparency that she is not providing now,” Lee said. Lee said Rogers was extremely ill and recovering from a stroke, so he reluctantly voted for Henyard, though he really had no clue about her background. “We had to have a mayor, and she was the only choice I could see at the time,” Lee said. Jeff Vorva / Daily SouthtownTiffany Henyard was presented with flowers from Illinois House Speaker Emanuel Chris Welch and Cook County Board President Toni Preckwinkle at her inauguration in May 2021. Seen as a breath of fresh air at a celebratory inauguration as first female Dolton mayor, clout heavy attendees included Illinois House Speaker Chris Welch and Cook County Board President Toni Preckwinkle, with former Circuit Court Clerk Dorothy Brown as transition leader and interim village administrator. Henyard even called on leaders to help her reach out to Chicago Mayor Lori Lightfoot regarding Dolton’s water debt. She had assembled what she called her dream team, and elected with her were Trustees Kiana Belcher, Jason House and Brittney Norwood along with Village Clerk Alison Key. They’re now on a ticket called Clean House, headed by House, that also includes former Trustee Edward Steave. Ironically, they also hired Lightfoot to investigate Henyard. Sought supervisor position As fights with trustees and opposition built in Dolton, Thornton Township Trustee Chris Gonzalez nominated Henyard to be township supervisor following the death of Frank Zuccarelli in January 2022. The move came after five failed votes by trustees to find a replacement as a midnight deadline neared to avoid a town hall meeting. “I really didn’t know her all that well. Obviously I knew she was the mayor of Dolton and stuff like that,” Gonzelez said. He said Henyard expressed interest in the supervisor position “if you guys can’t pick someone,” Gonzalez recalls Thornton Township Trustee Christopher Gonzalez, during a meeting Aug. 15, 2024, in South Holland. (Vincent D. Johnson/for the Daily Southtown) At the March 3, 2022, meeting, Gonzalez twice nominated township assessor Cassandra Elston, who he said Zuccarelli wanted to succeed him. However, a split in the board meant neither Elston nor other candidates received enough votes for appointment. He said he felt if Elston couldn’t be supervisor, the township would benefit from a young, female leader. “I honestly thought that she wanted to carry on Frank’s legacy, and obviously that’s not the case,” Gonzalez said. Zuccarelli was known as a Democratic Party powerhouse in the region, holding positions on the South Suburban College Board and within the Cook County Democratic Party before his death in January 2022 at age 70. Gov. J.B. Pritzker spoke at his wake, calling the late supervisor a “genuine champion” and someone who had lived “a brilliant life of service and friendship.” Gonzalez, who has since become Henyard’s most vocal critic on the Township Board, regrets the nomination. He said what he believes are her true colors were shown soon after she entered office, as she began improperly firing employees and telling “mistruths that I knew were mistruths.” Gonzalez said he questioned these behaviors from the start, leading administrator Keith Freeman, who has since been fired, to approach Gonzalez and ask what he could do to improve the relationship between the trustee and Henyard’s administration. “I said, ‘One of two things is going to happen here: you guys are going to be more transparent, or I’m going to be seen as the enemy. It doesn’t matter to me which one it is,'” Gonzalez said. “A lot of things come back around.” Lack of transparency Trustees in Dolton were also raising concerns about spending by Henyard, as she did not provide documentation to them, and she signed contracts and spent money without approval. A Las Vegas trip and building of an ice rink were among catalysts. Village Clerk Keys sought a restraining order in April 2022, claiming Henyard directed department heads and employees not to respond to requests for information made under the Freedom of Information Act, something the clerk’s office typically handled. Keys’ complaint said department heads and employees abided by Henyard’s order for fear of losing their jobs. Cook County Judge Anna Loftus denied the restraining order in August 2022, and the case has since languished in the circuit court. Dolton trustees, hearing of federal investigators collecting documents through subpoenas and even Village Hall visits, hired former Chicago Mayor Lori Lightfoot to examine Henyard’s administration and village finances. A preliminary report this summer by Lightfoot showed, since Henyard’s election, Dolton went from having a budget surplus to a significant deficit. Lightfoot is expected to release a more complete report on her findings in January. Former Chicago Mayor Lori Lightfoot talks about preliminary findings regarding Dolton Mayor Tiffany Henyard’s administration Aug. 8, 2024. Lightfoot was hired by Dolton trustees as a special investigator to look into the spending habits of Henyard. (Tess Crowley/Chicago Tribune) From the perspective of Thornton Trustee Gonzalez and many of the people since drawn to the drama surrounding ongoing investigations and “politricks,” as Henyard often says at meetings, lack of transparency has been a tenet of Henyard’s leadership. Gonzalez and Trustee Carmen Carlisle, who was appointed to the board after serving as Henyard’s assistant but soon became another self-proclaimed enemy of the administration, complained they have been cut off from almost all township communications and said they receive little to no information about motions the supervisor brings forward at meetings. Seeking answers The Daily Southtown sought records from Dolton in May 2023, and followed up again in August of that year. While the Freedom of Information Act requests were acknowledged as received, there was no response. In May 2024, lawyers for the Daily Southtown sent a letter to Dolton officials, including Henyard, outlining the lack of response and requesting the village adhere to the law and turn over records. It too was ignored. WGN also sought records in this time period without response, and requested the public access counselor in the Illinois Attorney General Kwame Raoul’s office review the request. In February 2024, the attorney general’s office issued a binding opinion ordering Dolton to produce the requested records. The village did not. WGN eventually won a court ruling demanding the documents be turned over, leading to stories on that station and in the Daily Southtown on some of Henyard’s spending in Dolton. Residents and other outside groups also sought answers. Documents obtained by the Daily Southtown show the attorney general’s office received more than 50 complaints of FOIA requests denied or ignored by Dolton between January 2021 and April of this year. The office did not provide all relevant documents in time for this article’s publication. The attorney general’s office also received 30 complaints of denied or ignored FOIA requests by Thornton Township between January 2022 and August of this year. The state comptroller also ordered a forced audit because Dolton has not filed annual financial reports. An auditing firm is now in place, but it could be six months before the financial reports might be ready, House said at a recent Village Board meeting. Until that happens, the comptroller is holding back from Dolton money it collects from things such as past-due traffic fines, amounting to more than $100,000. Uncertain future As Dolton and Thornton Township head into another election season, a cloud of uncertainty hangs over Henyard’s future. Her term both as mayor and supervisor end following the April election, and she has sought to keep both posts. She is a candidate in the February Democratic Primary for Dolton mayor, facing the challenge by the Clean House slate. A chaotic Democratic caucus last week appeared to keep Henyard’s name from the April 2025 ballot, as state Sen. Napoleon Harris clinched the Democratic Party’s nomination for supervisor along with a slate including Gonzalez for reelection as trustee. Henyard, who attempted to nominate herself for supervisor, was disqualified by party rules requiring candidates to run as a team of people filling every open position. Henyard has since threatened to file a court challenge to the caucus proceedings, calling them rigged against her. Henyard’s silence Henyard rarely returns phone calls or messages for response about her actions, including requests to be interviewed for this article. She does provide videos on social media channels, complaining about coverage in the media and treatment by trustees in both the village and the township. She also uses the platform to rail against her critics. Dolton Trustee Jason House presides over a Dolton Village Board meeting at the Lester Long Fieldhouse in Dolton Oct. 7, 2024. (Terrence Antonio James/Chicago Tribune) Henyard has repeatedly described Dolton trustees opposed to her as corrupt, and has long promised a town hall meeting where she said she will explain the village’s financial situation and how taxpayers’ money is spent, although that has yet to happen. On her Facebook page, Henyard describes herself as “The most powerful woman in the Southland of Chicago,” and calls herself “Supermayor,” a mash-up of her roles as township supervisor and Dolton mayor. Even as a federal investigation into her continues and has included Henyard’s ties to Thornton Township High School District 205 and a purported charity headed by Henyard, she has remained defiant. Lee said he is supporting the ticket led by House, and told Henyard at a Dec. 2 Village Board meeting, “you are on your way out.” During Henyard’s mayor’s report at that meeting, which tends to be a recitation of her accomplishments, she said she is “coming for everyone that defamed my name,” and, despite her Democratic credentials, again cited Republican President-elect Donald Trump. “I am going to come through on a landslide just like Trump did,” she said. “Dolton is going to see their mayor rise like a Phoenix.”