Kaitlin Bennett’s Winter Garden Lawsuit: Trespass Warning Rescinded

There is no Kaitlin Bennett Winter Garden lawsuit. Bennett was removed by police from the Winter Garden Farmers Market on June 21, 2025, and issued a trespass warning, but the City of Winter Garden rescinded that warning three days later after acknowledging the market sits on public property. No case has been filed in any Florida state or federal court over the incident.¹

What Happened at the Market

Bennett was filming interviews for her YouTube channel, “Kait’s Unsafe Space,” at the Downtown Pavilion where the Winter Garden Farmers Market operates. She was approaching attendees with political questions, including about Texas Representative Jasmine Crockett and statements about Trump supporters.²

A police officer first told Bennett she didn’t have permission to film and directed her to the sidewalk. Dana Brown, president of RTP Productions Management, the private company that runs the market’s weekly operations, initially told her she could continue. About an hour later, police and event staff returned and told Bennett to leave or be arrested. Officers escorted her out, and the Winter Garden Police Department issued a formal trespass notice.¹

Bennett later said a police supervisor told her the decision had been “handed down to him by the Chief of Police.”²

Why the City Rescinded the Trespass Warning

On June 24, 2025, City Manager Jon Williams issued a statement through the Downtown Winter Garden Facebook page. While a private corporation hosted the market, it operated on public property using “unclosed public right-of-way,” which meant the trespass warning could not legally stand. The police department rescinded it.¹

Williams said the reversal was not influenced by the negative social media attention Bennett’s followers directed at the city, answering simply “No” when asked. The city added that police staff would “be provided guidance to prevent future incidents of this nature.”¹ Bennett said the Chief of Police personally called her to apologize and lift the ban.²

Because the city withdrew the enforcement action and admitted its legal basis was faulty, the most obvious grounds for a federal civil rights suit dissolved before any filing.

What Winter Garden Did Afterward

At the June 26, 2025 City Commission meeting, Mayor John Rees said he and his family had received profanity-laced messages at their home from Bennett’s supporters.³

On July 24, 2025, the City Commission unanimously approved an ordinance regulating soliciting and peddling on public rights-of-way, including streets and sidewalks. The ordinance created a permit system and allowed homeowners and businesses to register on a no-solicitation list. It explicitly excluded political and religious canvassing from its definition of solicitation, applying only to cash and charitable donation requests.⁴

The Related Lakeland Dispute

Winter Garden was Bennett’s second Florida farmers market clash in about five weeks. On May 17, 2025, she was filming at the Lakeland Downtown Farmers Curb Market when Julie Townsend, executive director of the Lakeland Downtown Development Authority, asked her to relocate to the sidewalk, citing vendor complaints that Bennett’s crew and onlookers were blocking foot traffic. Lakeland police issued Bennett a trespass warning, and a vendor reportedly brandished a gun magazine at her. No charges were filed, and the city said no one was permanently trespassed from the market.⁵

On May 23, 2025, attorney Jonathan K. Hullihan of Remnant Law, a Mulberry-based nonprofit firm, sent a demand letter to the LDDA on Bennett’s behalf. The letter accused the LDDA of “impermissible content-based discrimination” for restricting Bennett’s journalistic and political speech while allowing commercial vendors to operate. It demanded the LDDA stop restricting protected speech, train staff on constitutional rights, provide written assurance that individuals could film and interview in public areas around the market, and investigate Townsend’s conduct. The letter warned that Bennett was prepared to pursue federal civil rights litigation.⁶

The LDDA board voted on June 26, 2025 not to send a written response. Members supported Townsend’s stated intent to protect vendors and directed staff to develop written guidelines for managing disruptions.⁷

Florida Attorney General James Uthmeier entered the dispute on July 11, 2025 with a letter to Townsend. Citing the U.S. Supreme Court’s ruling in United States v. Grace, Uthmeier argued that public streets and sidewalks are traditional public forums where the government cannot suppress political speech. He called Townsend’s stated goal of keeping the market “free of politics and religion” “unlawful viewpoint discrimination” and warned that future attempts to suppress lawful speech could expose the LDDA to legal liability. Townsend maintained her actions were about foot traffic, not content.⁸

Current Status

As of the latest available reporting, no lawsuit has been filed over either the Winter Garden or Lakeland incidents. The Winter Garden matter closed when the city rescinded the trespass warning and admitted the legal defect. The Lakeland matter sits in a standoff: the LDDA is not responding to Bennett’s legal team and is developing internal policies, while Remnant Law’s threat of federal civil rights litigation remains a threat rather than a filing.¹⁸

1
Winter Garden Vox. Winter Garden Rescinds Trespass Warning Given to Conservative Commentator
2
Orlando Sentinel. Commentary: Winter Garden Arrest Threat Violated First Amendment Rights
3
Winter Garden Vox. Liberty and Justice for Me but Not for Thee
4
Spectrum News 13. Winter Garden Solicitor Changes
5
Daily Ridge. City of Lakeland Provides Statement Regarding Incident Between Conservative Journalist, Police Officers
6
Lakeland Gazette. Kaitlin Bennett’s Attorney Warns Lakeland: Stop Chilling Free Speech or Face Lawsuit
7
The Ledger. LDDA Seeks Options for Dealing With Disruptors at Lakeland Market
8
The Ledger. Florida AG Takes a Side in LDDA vs. Kaitlin Bennett Conflict