Tourism Money, Cruise Ships, City Vendors and One Family’s 13 Checks: Who Is Bankrolling the Key West Mayor’s Race
The Key West race for mayor and city commission is the most expensive in history; here are the spheres of influence backing Mayor Danise Henriquez and how they relate to the Niles’ shadow PAC.
Ed. Note: The information in this report is sourced entirely from public records available through the Key West City Clerk’s Campaign Finance Portal and the Florida Department of Elections. Those resources are available at the end of the story. Analysis of down-ballot races is ongoing, and this story will be updated as new data becomes available.
KEY WEST — Follow the big checks in the Key West mayor’s race and they lead to the same few blocks of the tourism economy — the cruise-ship concessionaires, the hoteliers, the city’s own garbage, towing and concrete contractors — and, in nine cases, straight back to the political committee attacking Mayor Danise Henriquez’s chief rival.
An Above the Fold analysis of every contribution of $500 or more reported through July 30 shows Henriquez has collected $141,479.68 in large checks — 89 percent of her $158,469.72 war chest — from 159 contributions tied overwhelmingly to businesses that depend on City Hall for leases, permits, contracts and cruise-ship passengers.
Challenger Sam Kaufman’s money isn’t exactly a mirror image. Of his $169,629.51, just $61,150.50 — just 36 percent — came in checks of $500 or more, spread across 599 mostly small donations from retirees, small-business owners, attorneys and writers, including author Judy Blume.
And five of the nine donors funding Families and Friends for the Keys — the Jack Niles-chaired committee that has raised $51,270 and spent at least $17,394.86 with a Miami political consultant attacking Kaufman — also wrote checks directly to Henriquez, commission candidates Greg Sullivan and Juan Llera, or former commissioner Mark Rossi.
The tourism, hospitality and cruise ship blocks are giving on both ledgers.
The Tourism/Cruise Ship Bloc: $77,000 of the Mayor’s Money
More than half of Henriquez’s large-donor haul — roughly $77,000 — traces to tourism, cruise ship, lodging and hospitality interests, led by two families with more business before the city than any other: Swift and Walsh.
The Usual Suspects
The Swift network — $18,500 in 19 checks. Historic Tours of America, the Conch Tour Train-and-trolley empire built by Edwin O. Swift III, gave Henriquez $1,000 as a corporation — and so did its affiliates Tropical Shell & Gift, Treasures of the Florida Keys, Historic Properties Management, Conch Tour Train Inc., Buggy Bus Inc. and Sloans Landing. So did Ed Swift III personally. So did HTA employees and relatives: Timothy, Candice, Brooke and Megan Atwell; Sheri, Freddy and Kaitlyn Varela; Michael Cates; Gerald Hernandez Jr.; Alberto Machado; and accountant Stewart Appelrouth. Historic Tours of America is also a $10,000 donor to the Niles PAC.
The Walsh family — $12,100 in 13 checks, 12 of them in a single day. On June 11, twelve $500-to-$1,000 checks landed in Henriquez’s account from the family and executives behind Ocean Properties Ltd. — the Opal Key Resort, Sunset Key and cruise Pier B: Thomas, Sean, Patrick, Michelle, Michael, Mark and Camron Walsh, plus Pier B manager Michael Lanigan, Anna Falcone, Thomas McMurrain, Andrew Berger and Scott Luper. One check was recorded from “William Wash (Ocean Properties)” — an apparent misspelling of Walsh.
Six weeks later, on July 22, three Walsh-affiliated hotels — The Capitana, The Laureate and the Weather Station Inn, all registered to the same Portsmouth, N.H., suite — gave the Niles PAC $5,000 apiece, the same day the PAC paid Green Point Group $17,394.86.
Spottswood — $7,500 to Henriquez, and Spottswood Management Inc. — the hotel, banking and law dynasty that is the Niles PAC’s single largest donor at $15,000 — gave to Henriquez through a web of employees and affiliates: Suzanne Moore Real Estate Services and Moore & Spottswood CPA partner Randy Moore, Race World Offshore, Reel Conch Fishing, Brightwild’s David Walsh, retailer Manoj Mirpuri, First State Bank president Gary Carney, Robert Spottswood Sr. personally, and Stan and Dana Day. Spottswood Management also wrote Sullivan’s campaign two corporate checks totaling $3,977.05 — including one for $2,977.05 on April 14 that exceeds the $1,000-per-election limit unless reported as an in-kind or split contribution, a filing Above the Fold has asked the city clerk to clarify.
The restaurant-and-charter rounds. The Turek hospitality group — Garbo’s Grill, Mac’s Place, Hank’s Hair of the Dog Saloon, Danger Charters and affiliated LLCs, most registered to 15 Sunset Key Drive — delivered six $1,000 checks each to Henriquez, Sullivan and Llera, generally within the same week.
The Conch Republic Seafood Company circle (Casey Arnold, Randy Kassewitz, Mark Vasturo, Joseph Farrell, Paul Skoric, Monopoly Guy LLC, Key West Team Building) added $7,000 to Henriquez.
The Lay family of Summerland Key — Lay Management, Catered Affairs of Key West, Amy and Vianca Lay — gave Henriquez $3,971.25, Llera $1,500 and Sullivan $1,000, most of it bundled on single days in January and March.
The vendors: companies paid by the city, giving to the people who vote on their contracts
A second tier of Henriquez money comes from businesses holding or seeking city work — about $16,000 in all:
• Waste Management Inc. of Florida, the city’s residential garbage contractor, gave $1,000 each to Henriquez and Llera. It gave nothing to Sullivan — it doesn’t need to. Sullivan is a Waste Management area director. The company’s franchise runs through City Hall; its own executive is now running for a seat that votes on it.
• Arnold’s Auto & Marine Repair, holder of the city towing contract, gave $1,000 each to Henriquez, Sullivan and Llera.
• The Toppino construction network — Rockland Recycling, CT & Sons (Charley Toppino & Sons), 2537 North Highway 27 LLC and John Toppino personally, the Keys’ dominant concrete and fill contractor — gave Henriquez $3,000, Sullivan $4,000 and Llera $2,000.
• Gary’s Plumbing & Fire (Gary Centonze) gave $3,000 to Henriquez, $3,000 to Sullivan and $500 to Llera.
Et al.
The attorneys who represent the tourism bloc gave alongside their clients. Barton Smith — whose firm Smith Hawks represents the Walsh family’s Pier B interests — gave Henriquez $6,000 in one day, May 28, through Smith Hawks PL, Stock Island Holdings, Pelagic Marina Investments, Sunset Marina, Stockrock KW LLC and his own name.
The Horan family added $4,000 to Henriquez through attorney Darren Horan, Key West Treasure Chest LLC, Joan Lord-Papy and 3591 South Roosevelt Blvd. JV LLC.
The Hemingway Home itself (907 Whitehead Street Corp.) and operator Greg Harrison gave $2,000 to Henriquez, $1,000 to Sullivan and $1,000 to Llera.
The PACs: Same Names, Second Ledger
Layered over the direct giving is the committee money. The Southernmost Preservation Fund — the Ocean Reef-based state PAC chaired by longtime Ocean Reef Community Association president David Ritz, which has raised zero dollars this cycle — wrote $1,000 checks to Henriquez (July 14), Sullivan (July 16) and Llera (July 20), its first Key West city-race spending in a decade of existence.
On July 30, Keys Common Sense Conservatives — the PAC chaired by Florida Keys Mosquito Control board member Jill Cranney-Black — added $1,000 to Henriquez. Other members include State Attorney Dennis Ward, County Clerk Kevin Madok, School Board Chair John Dick and long-time County Commissioner David Rice.
And then there is Families and Friends for the Keys itself. Of its nine donors — Spottswood Management ($15,000), Historic Tours of America ($10,000), Ocean Reef resident Jeffery Cornfeld ($10,000), the three Walsh-affiliated hotels ($5,000 each), Denise Holland-Schmitt ($520), New Moon Management Group ($500) and Robert Mongelli ($250) — at least five overlap the candidates’ own donor rolls. New Moon Management, operating from planning board member Michael Browning’s 1128 Simonton St. office, gave $500 each to Sullivan and Rossi. Former planning board member Sam Holland gave $2,000 to Henriquez his Conch House BnB and Suncrest Mini-Storage. The Spottswood, HTA and Walsh overlaps are detailed above.
The pattern is consistent: the largest tourism-related operators in Key West are funding the mayor’s re-election directly, funding her allies down the ballot, and funding the only committee spending money against her chief opponent — while staying entirely off Kaufman’s donor list.
The Outliers
Rossi’s $12,471 campaign is mostly his own: a $5,000 candidate loan, plus small checks including $500 from Browning’s New Moon Management and $500 from commercial tenant Kit Carson.
Llera’s $20,832.32 relies almost entirely on the shared network: 16 of his 22 large checks match donors on Henriquez’s or Sullivan’s lists.
Rossi had pledged early on not to accept checks over $250, but several checks to $500 slipped through. Rossi told the media that he had misspoke and the larger checks were accepted without his knowledge.
Kaufman’s large-donor list, by contrast, shows no Swift, Spottswood, Walsh, Toppino, Turek or city-vendor money at all. His campaign saw
In a city where the commission votes on cruise-ship limits, hotel development, transient rentals and the contracts that keep the garbage picked up and the concrete poured, the August 18 ballot now carries an unusually legible price tag.
The industries that profit from more — more ships, more rooms, more visitors — have chosen their candidates, on both ledgers. The $33,854.04 the Niles PAC has raised but not yet reported spending suggests the second ledger isn’t finished writing.
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.
RESOURCES
Sources: City of Key West campaign treasurer’s reports (EasyVote portal) through July 30; Florida Division of Elections committee filings; Florida Division of Corporations (Sunbiz) registrations. Contribution figures reflect itemized contributions of $500 or more.
Mayor
District II
District IV
Sarah Compton Finance Reporting
District IV Finance Reporting
Families & Friends for the Keys
Donations
Expenditures
