SMOKING GUN: Mayor’s Campaign Page Reveals Link to Smear Texts Targeting Kaufman
Henriquez’ daughter allegedly replied ‘Done’ on campaign Facebook page post, suggesting illegal coordination between the Mayor’s camp and shadow PAC on derogatory voter texts outraging voters.



Ed. Note: This content is not affiliated with, authorized by, endorsed by or produced on behalf of any candidate, campaign or political committee in Monroe County.
KEY WEST, Fla. — A single-word reply on Mayor Danise Henriquez’s campaign Facebook page has ignited a firestorm over derogatory text messages targeting voters in the race for Key West Mayor, exposing what may be a smoking-gun link between the mayor’s campaign and the shadowy political action committee behind the smear tactics.
Outrage over the texts — sent to voters across the Island City by businessman Jack Niles and his PAC, Families & Friends for the Keys — reached a fever pitch Saturday morning when residents discovered that Ashley Henriquez McMahan, the mayor’s daughter and ostensible campaign and social media manager, had aledgedly replied “Done” with a checkmark on the mayor’s “Keep Danise ‘Dee Dee’ Henriquez for Key West Mayor” Facebook page to a resident who asked for the unsolicited texts to stop.
The reply suggests the Henriquez campaign was coordinating directly with Niles and his PAC — a potential violation of multiple Florida election statutes that prohibit candidates, their campaigns or their agents from working in concert with political action committees.
As of Saturday morning, Mayor Henriquez has yet to publicly disavow the smear campaign aimed at her opponent, District II City Commissioner Sam Kaufman.
Voters have flooded social media with complaints about the texts, many saying they continued to receive them even after replying “stop” to opt out.
WHAT THE LAW SAYS
The McMahan reply triggers a cascade of potential violations under Florida’s campaign finance statutes.
The Coordination Test
Florida Statute §106.011(12) defines an independent expenditure as one that is not controlled by, coordinated with, or made upon consultation with any candidate or campaign. The statute lists seven specific acts that convert a PAC’s spending into a coordinated expenditure — effectively making it an in-kind campaign contribution subject to strict limits. Among those triggers: communicating with the candidate or any agent about the expenditure, and making payments in cooperation, consultation, or concert with the candidate or campaign.
Ashley Henriquez McMahan’s one-word confirmation on the campaign’s own social media page — posted by the mayor’s daughter and campaign manager — satisfies at least two of those triggers. McMahan is also a contributor to her campaign.
Once any trigger is met, the PAC’s texting operation is no longer an independent expenditure. That sets off a chain of violations.
Unauthorized political texts
Because the coordination eliminates independent-expenditure status, Florida Statute §106.147(3) requires that the candidate must have filed prior written authorization with the qualifying officer before any texts were sent. If Mayor Henriquez never filed that authorization — and she has not acknowledged any connection to the texting campaign — both the PAC and the campaign are in violation.
Unapproved political advertising
Under §106.143(5)(a), any political advertisement not paid for by a candidate but offered on the candidate’s behalf — other than a true independent expenditure — must be approved in advance by the candidate. The advertisement must expressly state the candidate approved the content and must identify who paid for it. The derogatory texts carry no such approval or disclosure.
Excess contributions
Under §106.08, once coordination is established, every dollar the PAC spent on the texts becomes an in-kind contribution to the Henriquez campaign. For a municipal office, the contribution limit is $1,000. Mass political texting operations routinely run into the thousands or tens of thousands of dollars. Every dollar above the limit is an illegal excess contribution.
False Independent-expenditure Claims
If the PAC filed reports with the state claiming the texts were independent expenditures, or if the texts included disclaimers stating no candidate approved them, those filings and disclaimers are false in light of the coordination evidence. Under §106.071, failure to include required disclaimers or filing false ones is a first-degree misdemeanor.
Potential Penalties
The consequences are substantial. Under §106.19, anyone who knowingly and willfully accepts excess contributions, fails to report contributions, falsely reports, or makes prohibited expenditures commits a first-degree misdemeanor — punishable by up to one year in jail and a $1,000 fine per count. Multiple violations mean multiple counts.
Beyond criminal penalties, violators face a civil penalty equal to three times the amount of the illegal expenditure, paid to the state General Revenue Fund. If the PAC spent $10,000 on the texting operation, the civil penalty alone would be $30,000.
Unfortunately, Families & Friends for the Keys has yet to list any expenditures other than for an on-line donation processing service.
Those potentially exposed include Niles personally and as a PAC officer, the PAC itself, Mayor Henriquez as the candidate who benefited from the illegal coordination, and Ashley Henriquez McMahan as the campaign agent who facilitated it.
Under §106.25, the Florida Elections Commission has jurisdiction to investigate. Any person with information of a violation may file a sworn complaint.
The “Done ✓” reply on a public Facebook page by that pages administrator, who is also a campaign manager, and donor constitutes documentary evidence.
This is an evolving story. Watch this space.




