Court Cases

In August 2024, Robert Dillon’s life was irreparably changed when police wrongfully arrested him for a crime he never committed in a city he had never been to. He was falsely accused of trying to lure a child at a fast-food restaurant in Jacksonville Beach, more than 300 miles away from his home, after police ran a grainy image of the suspect through an AI-assisted facial recognition program, which incorrectly identified him as a possible match. Mr. Dillon, a 52-year-old resident of Fort Myers, Florida, is suing the Jacksonville Beach Police Department, as well as the Jacksonville and Pinellas County Sheriff’s Offices and two individual officers, for his wrongful arrest. Police arrested Mr. Dillon after they relied on the incorrect facial recognition technology result, let that result taint a subsequent photo lineup, and then applied for an arrest warrant while concealing information showing that Mr. Dillon could not have committed the crime he was being accused of. Facial recognition technology is fundamentally unreliable, often misidentifying people. And as similar wrongful arrests across the country have shown, following a facial recognition technology search with a photographic lineup is a recipe for misidentifications—a false match usually looks similar to the suspect, misleading witnesses who are asked to choose between that innocent lookalike and a set of filler photos that necessarily look less like the suspect. In this case, police also omitted from the warrant application key facts, including that the suspect was a “regular” at the restaurant, yet Mr. Dillon lived five hours away and had told police he had never been to Jacksonville Beach in his life, and that an automatic license plate reader database search showed no hits on Mr. Dillon’s car anywhere near the restaurant. Mr. Dillon is represented by the ACLU, ACLU of Florida, and the law firm of Hoguet Newman Regal & Kenney, LLP. His lawsuit seeks both monetary damages and injunctive relief, in the form of policy changes to help prevent police from wrongfully arresting other people due to reliance on facial recognition technology.

This case challenges the City of Clearwater’s rejection of thousands of citizen initiative petition signatures in violation of the law. The citizen-led initiative petition “Save the Garden” collected over 8,000 signatures through an all-volunteer effort to put a measure on the Clearwater ballot to require voter approval before the city transfers public rights-of-way in the downtown. The city rejected thousands of valid petitions, contrary to the rules laid out in the City Charter. The city also failed to specify the reasons why it invalidated signatures as required, and enforced a rule limiting who can lead initiative efforts, in violation of the First Amendment.

This case challenges the Village of Palmetto Bay’s retaliation against an elected councilmember for his protected political speech. After Charlie Kirk’s death, Palmetto Bay Councilmember Steve Cody posted political satire critical of Kirk’s views on gun rights. In response, the Village Council removed Cody from a committee and rescinded related representative roles—despite acknowledging that Cody’s comments were protected by the First Amendment.

Our client Naples Pride, a nonprofit that provides services and hosts events for the LGBTQ+ community, filed a federal lawsuit against the City of Naples and its entities for denying the non-profit organization a special events permit to host a family-friendly drag performance in one of the city’s public parks as part of its annual Pridefest celebration. The city’s refusal to grant a permit was part of a years-long effort to target drag performances and LGBTQ+ pride events in violation of the First Amendment. The complaint was filed on April 10, 2025. The district court granted a preliminary injunction on May 12, 2025, but the Eleventh Circuit — in a split, 2-1 decision — placed a stay on that ruling on June 6, 2025, the day before the event. The event went forward on June 7 with the drag performance indoors.

Michael James Jackson was sentenced to death in May 2023. If his resentencing had taken place just one month earlier, before Florida’s capital-sentencing law changed in April 2023, eight votes for death would have meant that he lived. If the trial judge had correctly applied the amended law to apply only prospectively, as the Legislature unambiguously commanded, only a unanimous jury vote could have resulted in death. In either case, the very same eight- to-four jury vote would have saved Mr. Jackson’s life. And even this on-the-cusp vote might have tilted in favor of life if the trial court had not failed to instruct the jury that, under Florida law, a life recommendation would be binding. A continuance would have allowed the court to confirm—with model jury instructions that came out shortly after Mr. Jackson was sentenced—the arguments Mr. Jackson’s attorneys were making all along: that the jury could not be lawfully instructed that its life vote would be a mere recommendation subject to the court’s approval rather than a binding determination that the court could not modify. The ACLU is assisting in the appeal and entered appearances in September 2023. Our briefing contends that the trial court’s improvised and inaccurate jury instructions violated state law and Supreme Court precedent and that Florida’s new statute allowing non-unanimity in capital sentencing violates the Sixth, Eighth, and Fourteenth Amendments. Briefing was complete in September 2024, and oral argument took place December 2024. The court issued its decision in December 2025, and we filed a motion for rehearing in January 2026.

On September 30, 2024, the Florida Department of Corrections issued a health services bulletin setting new rules for the medical care that would be provided to transgender people in its custody. Contrary to the medical mainstream, the bulletin suggests those seeking hormone therapy may have endured “short-termed delusions or beliefs which may later be changed and reversed” and recommended against providing any gender-affirming medical care unless extensive barriers were overcome. That same day, at Florida Department of Corrections facilities across the state, transgender inmates were rounded up and informed that FDC policy had been changed, “up to and including hormone therapy.” They were specifically told that they would no longer have access to clothing and grooming standards that accord with their gender identity and would have 30 days to comply. Transgender women like our clients Reiyn Keohane, Sasha Mendoza, and Sheila Diamond were told that those who did not cut their hair in compliance with male grooming standards would be forcibly shorn, and those who did not turn in their female undergarments and feminine canteen items would be disciplined. Transgender men like our clients Karter Jackson and Nelson Boothe were told that those who did not turn in their male undergarments and male canteen items would be disciplined. In October 2024, the ACLU filed emergency litigation on behalf of Reiyn — who has been receiving gender-affirming hormone therapy and clothing and grooming accommodations while in FDC custody since 2016—and a proposed class of transgender inmates with gender dysphoria, on the grounds that the new policy constitutes a violation of their Eighth Amendment right to medically necessary care. The ACLU previously filed a 2016 lawsuit on behalf of Reiyn that led to the now-rescinded policy permitting access to hormone therapy and female clothing and grooming accommodations for transgender women in FDC custody, which for more than six years permitted hundreds of transgender inmates to access needed gender-affirming care. On January 31, 2025, the district court denied the government’s motion to dismiss the case, and the parties proceeded to discovery. On October 22, 2025 the district granted class certification for all inmates in FDC custody with gender dysphoria who are denied social accommodations.

The American Civil Liberties Union of Florida filed a lawsuit on behalf of the Tallahassee Bail Fund against Gwendolyn Marshall, the Clerk of the Circuit Court and Comptroller for Leon County. The lawsuit challenges Clerk Marshall’s enforcement of Florida Statute § 903.286, which improperly confiscates charitable organizations’ money to punish them for helping accused persons access their freedom. This statute violates the Eighth Amendment by allowing clerks to use cash bail to impose criminal penalties on innocent parties, such as bail funds, which deprives them of the money that makes their operation possible. Our complaint was filed in August 2022. Summary-judgment briefing was completed in February 2023. On September 28, 2023, the court denied the motions for summary judgment, permitting some claims to proceed to trial. A trial was held on February 15, 2024, and on February 20, 2024, the district court ruled in our favor, holding the state statute unconstitutional as applied to our client, the Tallahassee Bail Fund. In practical terms, this means that when the Bail Fund deposits cash with the clerk to bail a person out of jail, the clerk can no longer keep it to pay that person’s fines, fees, and court costs if they later plead guilty. Instead, that money will go back to the Bail Fund, allowing them to use it to bail another person out of jail. This ruling will reduce wealth-based detention in Leon County. The government appealed, and we then cross-appealed.