OPINION: And in This Corner, the Usual Suspects …
An anti-endorsement for Key West’s August ballot. Early voting runs Aug. 3-15, and voters get their final say Aug. 18.
Danise Henriquez, Juan Llera, Greg Sullivan and Mark Rossi are asking Key West voters for more of the same donor rolls, the same alibis and the same finger-pointing that helped get this town into its current mess.
This is shaping up to be the most expensive municipal election in Island City history, and the people financing it aren’t strangers. They’re the vendors, contractors and hospitality dynasties that have been writing checks to city officials for decades.
Most of them live on Key Haven or in Cherokee, S.C. Or Okeechobee. Or Ocala. Or Chiefland.
One cheap donor has an organic farm in Homestead.
Most publications — Above the Fold among them — publish endorsements.
The Key West Citizen, well not so much.
But then again, Above the Fold isn’t like them.
BACKGROUND
Ladies and Gentlemen… Let’s Get Ready to Rummmbbbble!
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. It is solely the opinion of the journalist based on more than 25 years of covering politics in the Florida Keys and Key West, interactions with individual candidates and observations during political forums.
But here is where Above the Fold differs, and this is something I have never seen before: anti-endorsements.
Here is who NOT to vote for, and why.
The Money Trail Is the Gravy Train
Pull the campaign treasurer’s reports and the same names keep surfacing across the accounts of Henriquez, Llera and Sullivan: Arnold’s Towing, Waste Management employees and affiliates, Gary’s Plumbing & Fire and the corporation tied to the Ernest Hemingway Home and Museum.
Henriquez also collected checks from Jason and Gregory Barroso — one a firefighter, the other a plumber — who happen to be the brothers of sitting City Manager Brian Barroso.
The fingerprints of the Swift, Walsh and Spottswood empires are all over the crime scene, along with those of other well-connected individuals.
Llera, a Keys Energy Services board member, took money from the same Waste Management orbit and picked up an endorsement from the South Florida Police Benevolent Association. Sullivan is literally a senior regional manager for WM, the company holding the city’s trash contract.
Those don’t look like four independent candidacies.
They look like one donor class spreading its bets across four ballot lanes, wagering on continuity rather than change.
And Now a Word on Our Mayor
To say the mayor has an awkward relationship with the truth would be a massive understatement.
My ex tried to shoot me, and when she realized the gun wasn’t loaded, she pistol whipped me.
I have a better grasp of my relationship with the truth than he does.
Recently, the mayor has taken to friendly airwaves to claim she’s “accomplished more in 23 months” than her opponent or any previous administration, and that she’s completed more projects than her predecessors, a claim this outlet examines in the graphic below.
I will stipulate: She is rather skilled with the Supersized scissors.
She’s also credited herself with pulling in more state and federal funding in fiscal year 2025 than any prior administration, though Key West’s audited FY2025 financial statements have not yet been released, meaning that claim currently rests on assertion — or trust — rather than verifiable facts.
Both the mayor and City Manager Brian Barroso have made the false claims that “they couldn’t remember when anybody brought that kind of money back to Key West.”
Ad nauseum.
I have pointed this out previously, but this project gave me the opportunity to look at some quantitative facts.
Well, the city has had two mayors before Danise worth measuring against: Teri Johnston, who served from 2018 to 2024 after eight years as a city commissioner, and Craig Cates, mayor from 2009 to 2018 and later named “Mayor Emeritus” for his tenure. Here is what they actually accomplished:
I was told there would be no math, but last time I checked — 31.6m and $45.2m is more than $5.5.
Correct me if I am wrong.
They’re Endorsing Each Other’s Alibi
Henriquez’s framing — that today’s problems trace back to “previous administrations” — has become the connective tissue or gristle holding the establishment slate together, even as her own record sits squarely within the commission majority she now blames on the past.
Llera, Sullivan and Rossi have largely stayed on message rather than challenge that narrative.
That is convenient because challenging it would mean challenging many of the people financing their campaigns.
The Kaufman Attack Conveniently Skips the Math
The mayor’s coming attack on Kaufman is easy to predict: Paint him as a holdover from the previous administration that left her a “myriad of problems” to clean up.
But that framing requires ignoring every other name that sat at that table — and goring some scions of the past.
If Kaufman is guilty by association with 12 years of dysfunction, then the same brush must reach the city managers who ran the government during that period: Jim Scholl, Greg Veliz, Patti McLauchlin, Todd Stoughton, and Al Childress.
Also wrapped up in the mayor’s ruse are the commissioners who served alongside Kaufman, some for far longer: Jimmy Weekley (35 years,) Clayton Lopez (19), Billy Wardlow (15), Craig Cates (17) — now a Monroe County commissioner — as well as former commissioners Greg Davila and Judge Richard Payne.
So are the city attorneys who advised the commission during that span: Shawn Smith, Ron Ramsingh* and interim City Attorney Mayanne Downs.
I wonder how all of them feel about being painted with such a broad brush — tossed under the money bus driven not only by the mayor but by many of her donors.
Just spitballing here: I am guessing they are pissed.
Let’s Not Forget Carey’s Role — Or Henriquez’s, According to the Transcripts
Let’s not forget that District II Commissioner Lissette Carey — according to the Monroe County grand jury’s findings — testified that she allowed then-City Attorney Ron Ramsingh* to intimidate and coerce her into pulling the Corradino Report from a commission agenda.
The report examined problems in the Building Department under Raj Ramsingh*, Ron Ramsingh’s* brother. Carey testified that she feared the report would mention members of her own family.
They came out anyway, but to date, the Corradino Report has never seen the sunshine at a City Commission meeting.
Carey later co-sponsored the resolution that fired City Manager Al Childress without cause on June 26, 2024. She joined outgoing Commissioners Lopez, Wardlow and Weekley in a 4-3 vote. Kaufman, Hoover and Mayor Johnston dissented.
Childress had commissioned the Corradino Report that exposed problems in the Building Department under Raj Ramsingh and in Code Compliance under Jim Young — findings that preceded the grand jury indictments of the Bubba Bozo Trio.
BACKGROUND
BREAKING: New Grand Jury Report Calls For Sweeping Reform At City Hall
A Monroe County Grand Jury is calling for a sweeping overhaul of Key West’s government structure, planning regulations and oversight processes, warning that persistent inefficiencies and unclear rules continue to undermine transparency and public trust.
Henriquez was not yet seated on the dais when Childress was fired. But grand jury materials indicated that she and now-Vice Mayor Donie Lee acted as agents communicating the desire to terminate Childress to Lopez, Weekley and Wardlow.
If accurate, the ouster was not simply the independent decision of four sitting commissioners. It was part of a coordinated effort that included incoming officials positioned to benefit after the seats changed hands.
The grand jury’s final report described the ouster as “an orchestrated removal” intended to protect what jurors called a corrupt inner circle entrenched in fraud, nepotism and cronyism.
I watched, lived and covered it. I could not agree more.
The grand jury formally recommended that Carey resign her commission seat. She has not done so. It recommended Stoughton be fired. Never happened.
All the grand jury got was a Bronx cheer.
All of this unfolded under a part-time city attorney arrangement inside an office effectively run by members of the Ramsingh family, now facing multiple felony charges.
If Kaufman was involved in the plot, why did he vote to retain Childress?
Inquiring minds want to know.
Ramsingh, Ramsingh and Young: The Asterisk That Isn’t a Law Firm
BACKGROUND
THE FRAUDULENT AND CORRUPT ACTS OF THE BUBBA BOZO TRIO
Well, the Monroe County State Attorneys Office released the grand jury report delving into corruption at 1300 White Street and the dirty dealings by the Bubba Bozo Trio of disgraced (and likely disbarred) City Attorney Ron Ramsingh, his brother, former Chief Building Officer Raj Ramsingh, and now retired small-time thug, former Code Enforcement Director Jim Young.
The asterisk next to “Ramsingh, Ramsingh and Young” isn’t a typo or a citation.
It’s City Hall telling you plainly that this isn’t a law firm. It’s a family affair.
Ron Ramsingh* was the city attorney. His brother, Raj Ramsingh*, was the chief building official. Both were indicted alongside former Code Enforcement Director Jim Young* after investigators accused them of deleting, altering or withholding text messages subpoenaed during the state investigation into Childress’ June 2024 firing.
Additional indictments accused Raj Ramsingh* of official misconduct involving building records and organized fraud tied to an alleged scheme exceeding $50,000.
BACKGROUND
Three Key West Employees Indicted
The Key West City Commission will meet in a special session on Monday, April 21 at 5 p.m. The meeting will be televised.
Ron Ramsingh* turned over 73 text messages to investigators, according to the grand jury report. Phone records showed 366 messages exchanged with his brother — leaving 293 messages that were not disclosed.
Grand jurors also concluded that Young’s close relationship with Ron and Raj Ramsingh* hindered his ability to think and act objectively.
That is not outside oversight failing to catch insider corruption.
That is insiders overseeing insiders — by blood.
All three men are presumed innocent until proved guilty.
The PAC They Won’t Disown
The attack ads hammering Kaufman come from Families $ Friends for the Keys, a political committee chaired by Conch and Florida State University athletic supporter Jack Niles.
The PAC has raised $51,270 from nine donors to date and reported paying $17,394.86 to Green Point Group, a Miami political consulting firm also paid by the Henriquez campaign.
Five of those seven donors also wrote checks directly to Henriquez, Sullivan, Llera or Rossi.
That means the PAC is hardly independent in any meaningful political sense. It is the same donor-class money washed through a second bank account, giving the candidates plausible deniability while the PAC does their political dirty tricks — ala Watergate and a bunch of clowns breaking into DNC office.
Rossi, unfortunately, belongs on this list of the complicit. He has not publicly distanced himself from or disavowed the Niles-orchestrated attacks benefiting the mayor’s camp, despite ample opportunities at candidate forums and during his own media appearances.
Food Banks vs. Attack Ads: The Numbers That Should Embarrass Everyone
It took a formal commissioner petition and weeks of public pressure in November 2025 to persuade the city to allocate $40,000 in emergency food-pantry assistance during the federal government shutdown.
The commission later authorized up to $75,000 in January 2026, but only after sustained public advocacy.
BACKGROUND
City Hall Ignored Warning About Food Insecurity Crisis Before Rejecting Emergency Aid, Email Shows
Tone-deaf comments from Mayor Danise Henriquez about families “living paycheck to paycheck” ignited backlash Tuesday morning — especially after Above the Fold confirmed that both the mayor and City Manager Brian Barroso were warned nearly a month earlier about a rapidly escalating food insecurity crisis in Key West and never responded.
Compare that grinding process with nine private donors assembling $51,270 in weeks and spending roughly a third of it through a consulting firm involved in an attack campaign — with no public vote, hearing or debate required.
One side had to beg for pantry money.
The other had spare change for a political hit job.
Their plates were overflowing.
WM’s Monopoly Grip on Key West Trash
Waste Management Inc. of Florida holds the exclusive contract for residential and commercial garbage, recycling and yard-waste collection in Key West.
Every household and business is effectively locked into one hauler.
On Dec. 2, 2025, the commission approved the second and final four-year extension of the contract, carrying WM’s exclusivity through the next commission term.
BACKGROUND
WHAT A DUMP: From Sewage Scandal to City Hall, Waste Management’s Greg Sullivan Seeks District V Commission Seat
KEY WEST — Greg Sullivan, the Waste Management area manager whose name became synonymous with a 2023 criminal investigation into the illegal dumping of raw sewage at Little Hamaca Park, want’s your vote for Key West City Commission District V seat.
The city later moved toward a volume- and weight-based enforcement structure that included a $295 annual charge for an additional garbage cart. WM crews were authorized to identify noncompliant carts using address information supplied by the city.
That leaves a private contractor helping enforce the same fee structure from which it benefits — during an election cycle in which one of its senior regional managers, Greg Sullivan, is running for the City Commission.
Sullivan has said he does not believe a Waste Management issue would come before the dais if he were elected.
Recent changes affecting Haitian Temporary Protected Status could, however, significantly disrupt parts of South Florida’s workforce. If that affected WM’s local operations or costs, the company could seek contract changes or emergency relief requiring commission consideration.
That is not a hypothetical conflict that voters should simply wave away.
How the Commission Actually Voted on These Contracts
The voting record complicates any effort to paint Kaufman as equally complicit in the vendor-driven machine — and adds nuance this column needs to remain fair.
On June 4, 2025, Kaufman moved to amend the Arnold’s Towing renewal by incorporating safeguards recommended by the city’s procurement manager before extending the company’s exclusive contract through 2027.
Commissioner Monica Haskell seconded the motion.
The amendment failed 5-2. Vice Mayor Lissette Carey, Commissioners Aaron Castillo, Mary Lou Hoover and Donie Lee, and Mayor Henriquez voted it down. Kaufman and Haskell were the only votes for tighter terms.
The unamended Arnold’s contract then passed 6-1, with Kaufman casting the sole dissenting vote against renewing the exclusive agreement with a company whose owners or affiliates donated to Henriquez, Llera and Sullivan.
The WM extension tells a similar story.
That extension, sponsored by City Manager Barroso, passed Jan. 6, 2026, with no comparable amendment fight and only one recorded vote of dissent — Kaufman.
On towing, at least one commissioner publicly challenged the donor-favored terms and put his name behind proposed safeguards.
On trash, the monopoly extension that framed the city’s later changes sailed through without opposition.
A note on precision: Gary’s Plumbing & Fire, owned by Gary Centonze and a donor to Sullivan and Henriquez, advertises services to municipal customers. But I found no documented City of Key West procurement contract or commission vote confirming a direct city vendor agreement comparable to the WM and Arnold’s Towing contracts.
That distinction matters.
One is a campaign donor that advertises municipal work. The other two hold documented, commission-approved exclusive contracts with the city.
Vendor Money, Years of Consequences
Years of donations flowing toward Henriquez and other establishment candidates — along with money routed to a recently aligned PAC — do not prove that any single vote was bought.
I guess you can’t really blame those that came before you without concrete facts about wrong doing, right?
But the overlapping interests are precisely what genuine reformers disclose, confront and, when legally required, recuse themselves from.
They do not wait for voters to discover the connections in campaign finance reports and legislative minutes two months before an election.
Honestly, I shouldn’t have to work this hard.
Then came the awards of large swaths of Mallory Square to entities connected to Ed Swift and Historic Tours of America, premature franchise-agreement extensions that could raise antitrust concerns and plans to increase dock space behind the Key West Aquarium tying it in with Mallory square.
That dock expansion could connect with the Cable Hut and Hospitality House properties included in the Mallory Square agreement.
Apparently, those public decisions were worth the Swift interests’ personal and corporate campaign investments.
A Word on District II
I have been called a Kaufman shill, a Soros plant and a paid political operative.
I have been accused of accepting money from candidates to write favorable stories — and worse.
Of course, none of that is true.
And if it were, I am still waiting for my checks.
This is my grist, my mill and my métier.
Many readers were surprised when I endorsed Rossi over Bobi Lore and Wayne Garcia over Sarah Compton earlier in this election cycle.
I stand by my original District IV endorsement of Wayne Garcia, but I need to revisit District II.
I consider both Lore and Rossi personal friends, and I explained my reasoning in previous endorsements.
But Rossi’s continued public alignment with the mayor’s camp — through media appearances and campaign signs and banners promoting the Chamber-friendly slate at his Duval Street property — has changed my assessment.
Add the minor campaign finance issues I have already covered and his uneven performance at the League of Women Voters forum, and my position has shifted.
In the interest of fairness, I am moving my District II endorsement to neutral.
I believe either candidate could serve the district’s constituents well. It is Rossi’s establishment ties to the mayor and his unwillingness to distance himself from her camp’s tactics that leave me too uncomfortable to go all in for him now.
And now, neither of them will likely talk to me.
That sucks.
As my grandmother put it, “in this business you crack eggs first and apologize to the omelette later.”
Or
“Qu'il advienne que pourra.”
Or
“Lass die Eier zerbrechen, wo sie wollen.“
Or
“Kite sa rive jan l dwe rive.”
Or
“Que se rompan los huevos donde tengan que romperse.“
Or
“будь що буде“
So, there it is.
Let somebody say I am not fair.
In a Nutshell
Strip away the yard signs and state-of-the-city speeches, and what remains in Key West is a ledger:
Nine PAC donors.
One political committee.
A monopoly trash contract.
And text messages and four-color mailers nobody wants.
Two brothers indicted alongside another senior city official.
A firefighter and a plumber writing campaign checks to their brother’s political boss.
And a mayor who wants credit for cleaning up messes her own political network helped create — and, according to grand jury evidence, may have helped orchestrate.
Voters do not need a conspiracy theory to see it.
This message is tinfoil approved. It should make its way home, anyway if you are a decent human being.
One Human Family.
They need the campaign finance reports, meeting minutes, grand jury transcripts and the willingness to ask why the same names keep cashing checks no matter who appears on the ballot.
On Aug. 18, the question is not who inherited Key West’s problems.
The real question is who has been cashing in on them the whole time.
I think you know.
VOTE.