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.
Just a point of clarification… these infographics only looked at donations of $500 or more, up to the maximum individual donation of $1,000.
KEY WEST, Fla. — In an effort to bring greater transparency to campaign financing in what has become the most expensive city election in Key West history, I continued crunching the numbers so you wouldn’t have to — distilling hundreds of contributions into an easy-to-read, palatable infographic format.
On Friday, we took an in-depth look at the race for mayor between incumbent Danise Henriquez and her challenger, District II Commissioner Sam Kaufman. I have included those graphics again for context, allowing readers to see exactly who is backing which horse in the down-ballot races.
Tourism Money, Cruise Ships, City Vendors and One Family’s 13 Checks: Who Is Bankrolling the Key West Mayor’s Race
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.
Suffice it to say, the candidates who could be considered the “reform slate” — Kaufman, Bobi Lore, Sarah Compton, Wayne Garcia and Chris Massicotte — received none of the campaign-season gratuitites being scattered like breadcrumbs for ducks by Key West’s merchant princes.
Instead, that money flowed heavily toward Henriquez, Juan Llera and Greg Sullivan — the candidates most closely associated with the city’s business and political establishment. Many of those donors or their affiliated businesses, properties and projects have benefited from the largesse of Key West city commissions — and “establishment candidates” in years past.
One other unusual donation pattern that seems to be cropping up is that of appointed members of Key West municipal boards donating — to the establishment candidates.
Conventional wisdom would say don’t donate at all, or donate to everybody.
But that is a different strategy than the one employed by long-time Planning Board members Michael Browning (New Moon Management) and George Wallace, as well as Key West Bight Board member Steve Henson.
A very unusual — if not unethical move.
Mayor’s Race
The money behind the mayor’s race tells a familiar Key West story. Henriquez has drawn heavy support from many of the city’s usual political donors — business owners and special interests whose companies, properties or projects have benefited from favorable City Commission decisions over the years.
Many of those same interests are backing other establishment or “chamber slate” candidates, including Llera and Sullivan, in an apparent effort to preserve business as usual at City Hall.
The network extends beyond direct campaign contributions. Families & Friends for the Keys, the shadow PAC controlled by Conch athletic supporter Jack Niles, has spent recent weeks attacking Kaufman while promoting candidates aligned with the same political establishment.
The move is ironic due to the amount of vitriol the smear campaign garnered from voters around the Island City that were enraged after receiving multiple texts and mailers despite opting out of the electronic communications. The temperature around the island with the motivated electorate is that they would rather not vote against anybody engaged in or condoning that sort of campaigning.
None of the establishment candidates — most notably the mayor — have ever publicly disavowed the message or the source.
Although Kaufman dominated the regular fundraising with hundreds of small, grassroots donations, his total pales in comparison when Families & Freinds of the Keys money is figured in to the mayor’s till
RESOURCES
District II
The District II money reflects the broader effort by Key West’s political and business establishment to influence races across the city. While Lore has received support from a mix of individual donors, Mark Rossi has recently benefited from positive text messages sent by Families & Friends for the Keys — the same Niles-controlled shadow PAC attacking Kaufman in the mayor’s race.
The messages suggest the PAC’s involvement extends well beyond the mayoral contest and is part of a wider push to elect candidates viewed as friendly to the Chamber of Commerce, its agenda and the special interests seeking to maintain business as usual at City Hall.
This district is somewhat of an outlier; Lore has a solid financial base while Rossi has raised the second least money of any candidate. He said early on that he would not accept checks over $250, but several slipped past him; for the most part, however, Rossi has self-funded his campaign.
Lore on the other hand has displayed a solid donor base and recieved the largest donation ($2,500) of any Democratic candidate (although City races are non partisan) from the Monroe County Democratic Election Committee PAC.
The PAC donated to every reform candidate in the election.
RESOURCES
District IV
In District IV, Llera has attracted support from many of the same familiar donors backing Henriquez and other establishment candidates. The usual suspects of Spottswood, Turek, Toppino, Lay and Swift show up as well as several City contractors: Arnold’s Towing and Waste Management.
Those contributors include individuals and business interests whose companies, developments or projects have benefited from City Commission majority decisions in years past.
The overlap reinforces the picture of a coordinated “chamber slate” financed by special interests seeking to protect their access and preserve the status quo at City Hall. Compton and Garcia, by comparison, have not drawn the same concentration of support from those traditional power brokers.
Garcia has largely self-funded his own campaign, raising just but did receive a $1,000 donations from Zach Bentley, Sr. And $500 each from the Garcia Law Firm and the Monroe County DEC PAC and has totaled just $8,353.68
Compton also received a $500 donation from the DEC, as well as overlapping with other reform candidates with donations from author Judy Blume and her husband, George Cooper.
One item that does stand out — ironically — is that in a race where the cruise industry has been a focal point, particularly with the Outer Mole in play, Compton is the only candidate to accept donations directly from a cruise line. She received a total of $4,516.25 from the family that owns boutique operator American Cruise Lines — the small ships that dock at Mallory Square seasonally.
RESOURCES
Sarah Compton Finance Reporting
District V
The establishment’s influence is also visible in District V, where Sullivan has received support from many of the same donors and business interests backing Henriquez and Llera. Despite that, he trails Massicotte by roughly $12,000
Over the past several days, Families & Friends for the Keys has also sent positive text messages promoting Sullivan, even as the Niles-controlled PAC continues attacking Kaufman in the mayor’s race.
Again, District V is almost a mirror image of the other races; establishment donors backing the establishment candidates, and smaller donors with no ties to special interests backing the reform candidates.
RESOURCES
Taken together, the campaign contributions and PAC messaging point to a broader effort to elect a Chamber of Commerce-friendly slate — Henriquez, Llera, Rossi and Sullivan — that appears more receptive to development, a possible expansion of the city’s limited transient rental permits (according to Henriquez in a recent interview,) and fewer obstacles in the building and permitting process. Just as important, their election would help preserve the network of political and business relationships that has long influenced decisions on the island and at 1300 White Street.
Standing in the way are four candidates hoping not merely to slow that machine, but to break the wheel altogether.
Whether there is enough runway to land that plane remains to be seen. That will be unpacked and baked in by voters on Aug. 18. The rest will be cascaded to the public following the vote tally.
But money does not cast ballots. In fact, the majority of donors to the establishment side of the ledger can’t even vote, as they live in Key Haven and beyond.
But if the volume of small, grassroots contributions from residents outside the city’s business and development establishment is any indication, the old order may not be as secure as its benefactors believe.
That includes working Conchs who are tired of being taken for granted by the island’s big bosses — told they should feel fortunate merely to have jobs while the wealth, influence and opportunity trickle steadily upward.
Key West’s landed gentry and appointed municipal board members have placed their bets on the establishment slate. Only time will tell whether those wagers pay off — or come up snake eyes.
For the first time in a long time, however, the wheel does not merely look vulnerable.
It feels like it might just fly off altogether and hit somebody on the head.
Ed. Note: Regardless of your political affiliation or what you believe in, I can’t tell you who to vote for. But what I can tell you to do is VOTE! If you don’t, then you have forfeited your right to complain.
I unfortunately believe that you have hit the nail on the head. I am still trying to figure out if the MAGAtz moved here or if they were here all along and just suddenly feel emboldened.
This is why we are of common mind and purpose. Wait till the morning.
I wrap everything up.