Shadow PAC and Mayor’s Campaign Exposed Paying Same Miami Political Firm; Walsh Hotel Empire Pumps $15,000 Into Niles Operation.
Financial filings reveal Green Point Group collected more than $61k from Henriquez and the Niles-controlled PAC behind the attack texts and mailers that have enraged Key West 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. — The shadow political action committee whose unsolicited attack text messages and glossy smear mailers have pissed off hundreds of Key West voters shares the same Miami political consulting firm as Mayor Danise Henriquez’s re-election campaign, according to campaign finance records obtained and reviewed by Above the Fold.
At the same time, the billionaire Walsh family — the New Hampshire-based hospitality dynasty behind the Capitana, the Laureate and the Weatherstation Inn — has pumped $15,000 into the PAC through its three Key West hotel properties, not to be outdone by Spottswood Management Inc. as the smear operation’s largest donor.
Campaign treasurer’s reports filed with the Key West City Clerk Show Henriquez paid Green Point Group Corp. of Miami a total of $43.747.96 across eight transactions between May 18 and July 16. Families & Friends for the Keys, the PAC controlled by businessman and former standout Key West jock Jack Niles, paid the same firm $17,394.86 in four transactions on July 22, according to filings with the Florida Division of Elections.
Combined, the two operations funneled $61,142.82 to the same political services firm at the same address — 14629 SW 104th St., Suite 260, Miami — during the same election cycle.
Until now, there had been no documented financial link between the mayor’s campaign and the PAC that has carpet-bombed voters with derogatory text messages and slick four-color glossy mailers attacking District II City Commissioner and mayoral candidate Sam Kaufman.
The shared vendor changes that, and also complicates things for the candidate and the PAC.
FOLLOW THE MONEY
Henriquez’s payments to Green Point Group span three consecutive reporting periods:
Her Q2 treasurer’s report, covering April 1 through May 31, shows two payments on May 18 totaling $12,750 — a $10,000 payment and a $2,750 payment -- both listed as “consulting services.”
The mayor’s P2 report, covering June 13 through June 26 and filed with the city clerk July 4, reveals six additional payments on June 18 totaling $12,997.96. Those payments were itemized by service:
Photos, video production: $4,650.00
Direct mail: $3,500.00
Website: $2,000.00
Fans: $1,159.38
Direct mail: $1,110.58
Walk piece material: $578.00
Her P3 report, covering June 27 through July 10 and filed July 16, reveals three more payments on July 2 totaling $18,000:
Advertising: $11,000.00
Direct mail: $3,500.00
Direct mail: $3,500.00
The services are the building blocks of a political campaign — the same direct mail, the same walk pieces, the same voter contact materials that any consulting firm would produce for a candidate or, for that matter, a PAC — totalling $43.747.96.
The Niles PAC’s filings with the Florida Division of Elections show four payments to Green Point Group on July 22 totaling $17,394.86:
$3,047.00
$4,782.62
$4,782.62
$4,782.62
Those payments came after months of the PAC reporting virtually no expenditures despite flooding voters’ phones and mailboxes with attack messages.
For somebody that made his living with the tagline “Don’t Drive the Miles, Head on Over to Niles,” both the former car dealer and the mayor seemed to eschew that motto when they required somebody to do their dirty work.
KEY WEST vs. THE REAL WORLD
The scale of spending in the 2026 Key West mayor’s race is without precedent for a city of roughly 25,000 year-round residents.
Combined fundraising by the two candidates has already surpassed $290,000, not counting the $51,270 raised by Niles’ shadow PAC.
Although Kaufman out-raised Henriquez, primarily with donations less than $100, the mayor had 141 donations at the maximum of $1,000 from pro-cruise ship and entrenched chamber of commerce special interests and just a smattering of small $17 donations which were a ham handed attempt to show that she had support from grassroots voters; the promotion was a play on “$17 for #17,” a reference to her husbands uniform numbers as coach of the KWHS Conchs baseball team.
Including Niles war chest, the mayor’s total potential spend tops $202,000 — so far, with just under three weeks to go.
When Teri Johnston won the mayor’s office in 2018, she raised $116,000 and spent $111,330 — figures considered remarkable at the time. Her opponent spent less than $16,000. The current race has nearly tripled those totals, with Henriquez alone paying more to a single Miami consulting firm than Johnston’s opponent raised in the entire race.
By comparison, Orlando — a city of roughly 315,000 people, more than 12 times Key West’s population — saw its 2023 mayoral race top out at about $512,000 in total fundraising. Incumbent Buddy Dyer raised $480,000 and spent $328,000 to win a fifth term. His closest challenger, former City Commissioner Samuel Ings, raised just $32,000. No outside PAC played a significant role.
In Miami, a city of 440,000 residents, the 2025 mayoral contest is on track to be one of the most expensive municipal races in Florida history. Former Commissioner Joe Carollo has amassed a $2.5 million war chest between his campaign account and a political committee. Former County Commissioner Eileen Higgins raised nearly $480,000 in a single quarter. Former City Manager Emilio Gonzalez pulled in $750,000 through his campaign and a supporting PAC. Those figures reflect the financial scale of a major metropolitan contest — a scale that Key West’s 2026 race is beginning to approach on a per-capita basis.
THE TIMELINE
The timeline tells the story. Henriquez began paying Green Point Group on May 18. She made a second round of payments on June 18, filing on June 26. Her third payment processed on July 10 and was reported them on July 18.
The PAC made its payments on July 22. Their business with Green Point overlapped.
That means the mayor was actively paying Green Point Group for campaign services direct mail, walk piece material, video production — at the same time the smear campaign against her opponent was being designed, printed and distributed. Green Point Group was already under contract with the Henriquez campaign when it began doing work for the Niles PAC. In the language of Florida election law, a consultant under contract with a candidate who then performs services for a PAC supporting that candidate has effectively become an agent of the campaign.
The legal implications of that relationship are significant. Florida Statute 106.011(12) lists seven specific triggers that can convert a PAC’s spending from an independent expenditure into an illegal coordinated one -- and the use of a shared vendor or consultant is among them. Above the Fold will examine those triggers and their consequences in detail in a forthcoming report.
THE WALSH DONATION
The Walsh family’s $15,000 contribution to Families & Friends for the Keys was split across three Key West hotel properties, all filed on July 22 — the same day the PAC paid Green Point Group:
The Capitana, 2401 N. Roosevelt Blvd.: $5,000
The Laureate Key West, 3444 N. Roosevelt Blvd.: $5,000
Weather Station Inn, 57 Front St.: $5,000
All three checks list the same corporate address: 1000 Market Street, Building 1, Suite 300, Portsmouth, N.H. — the headquarters of Ocean Properties, Ltd., the Walsh family’s privately held hotel empire. The company operates more than 100 hotels across the United States and Canada, employs more than 6,000 people and controls at least 119 active Florida business entities, according to state corporate records obtained and reviewed by Above the Fold.
The contribution ties the Walsh family with Spottswood Management Inc. for the largest single-source donation to the PAC at $15,000 each.
THE NILES CIRCLE
The financial entanglement between the Niles PAC and the Henriquez campaign extends beyond the shared consultant.
A review of the mayor’s P2 campaign finance report reveals that four members of the Niles family donated directly to the Henriquez campaign on June 17, the same family whose patriarch controls the PAC attacking her opponent:
Lisette Niles, 16 Evergreen Ln., Key West: $17
Scarlet Niles, 16 Evergreen Ln., Key West: $17
Julia Niles, 16 Evergreen Ln., Key West: $17
Kellie Niles, 3737 Flagler Ave., Key West: $17
The address at 16 Evergreen Lane is the home of Niles and his family.
Several of the PAC’s major donors also appear in the campaign finance reports of Henriquez and other Key West candidates, including Greg Sullivan and Juan Llera. The same pool of special-interest money is flowing to the PAC and to the candidates it appears designed to benefit — a pattern that raises questions about the independence of the entire operation.
THE DONORS
The PAC’s war chest now stands at $51,270, according to the Florida Division of Elections. Every dollar came from just nine sources:
Spottswood Management Inc. (506 Fleming St., Key West): $15,000
The Capitana (Walsh/Ocean Properties, Portsmouth, N.H.): $5,000
The Laureate Key West (Walsh/Ocean Properties, Portsmouth, N.H.): $5,000
Weather Station Inn (Walsh/Ocean Properties, Portsmouth, N.H.): $5,000
Historic Tours of America Inc. (201 Front St., Key West): $10,000
Cornfeld Jeffery (3850 Hollywood Blvd., Hollywood, Fla.): $10,000
Denise Holland-Schmitt (11100 Overseas Hwy., Marathon): $520
New Moon Management Group LLC ([Planning board member and Bascom Grooms Realty Associate Michael Browning] 1128 Simonton St., Key West): $500
Mongelli Robert ([Roostica; Hogfish Bar & Grill] 3821 Eagle Ave., Key West): $250
Several of those same donors also contributed directly to the Henriquez campaign.
On the expenditure side, the PAC has reported $17,415.96 — $17,394.86 to Green Point Group and $21.10 to Anedot, an online donation processor. That means $33,854.04 of the PAC’s war chest remains unaccounted for in its filings.
Although the mailings continue to trickle into people’s mailboxes, the unwanted smear texts have stopped for now.
Annoyed about being bothered by a candidate they would never support, some voters have taken to social media to share their own memes about the mayor:
BACKGROUND
Mayor Henriquez has never even addressed or disavowed the smear campaign or acknowledged any involvement with the PAC. Her only public response to questions about the shadow operation has been to accuse her opponent and his supporters of pushing “false, negative narratives” — a characterization that becomes harder to sustain with each new financial filing.
Voters head to the polls Aug. 18 to decide who will lead Key West for the next two years.
This is more than an evolving story. Watch this space.
Above the Fold will publish a detailed examination of the legal implications under Florida’s campaign coordination statutes and what it could mean for the players involved on Tuesday morning.
Sam Kaufman has been in office for 12 years? So why is running as the “new” candidate???
Continued excellent reporting bringing to light facts that otherwise would go un-reported by the other papers. Thank you for the service.