Complaint Targets Key West Mayoral Survey Over Missing Campaign Disclosures

Jeffrey Siegel, chair of the political committee A Clean Slate for Key West, filed a formal complaint with the Monroe County Supervisor of Elections alleging that an email survey circulated to Key West voters during the 2026 mayoral race crossed the line from neutral polling into undisclosed political advertising.

The survey, which identified its sender as IH Strategies, presented recipients with statements about both incumbent Mayor Danise "DeeDee" Henriquez and challenger Sam Kaufman, a sitting Key West City Commissioner, and asked whether the framed language would make them more or less likely to support a given candidate. Siegel's complaint contends that structure transforms the email from a legitimate survey into campaign messaging that Florida law requires to carry a sponsor disclosure.

One item highlighted in the complaint reads: "Upholding her promise to bring transparency to City Hall, DeeDee Henriquez created a progress tracker on the city's website to keep residents informed about anti-corruption reforms in Key West. Does this information make you more likely or less likely to vote for Henriquez, or does it make no difference to you?" The complaint argues that presenting normative, pro-candidate statements and soliciting attitudinal responses meets the legal threshold for political advertising, regardless of the polling format it mimics.

Florida law requires political communications to carry disclaimers identifying who paid for them. Whether a survey triggers that obligation depends on its content, timing, and distribution method. Because the IH Strategies email named active candidates and tested specific pro-candidate talking points, the complaint argues it should have identified the sponsoring individual, campaign, or committee. Who commissioned the survey and how widely it was distributed remain central unanswered questions.

The Monroe County Supervisor of Elections will now review the complaint and determine whether to pursue enforcement, mediate a resolution, or refer the matter to the Florida Division of Elections or the Florida Elections Commission. If authorities find a violation, the responsible party could face amended reporting requirements, corrective disclosures, or administrative penalties.

The filing arrives as the Henriquez-Kaufman contest draws close scrutiny across the island. The outcome could set a practical precedent for how political operatives and outside groups label their outreach in Key West for the rest of the cycle.