Henriquez Leads Q1 Fundraising, Field Trails Kaufman Overall in Key West Races

Business-backed surge contrasts with resident-driven donor base shaping mayoral and commission contests.

From left, incumbent Mayor Danise Henriquez led first-quarter donations but still lags far behind challenger Sam Kaufman.

---

Ed. Note: With all candidates now reporting donations for Quarter 1 in the 2026 election cycle, a clearer picture is coming into focus. With each candidate, their top-tier donors and associations are listed. Also with each candidate is a link to their official Q1 filings. You may also visit the City website for more campaign information. Stay tuned to Above the Fold for more in-depth election analysis.

---

---

Incumbent Mayor Danise Henriquez posted the strongest Quarter 1 fundraising total among Key West’s 2026 candidates, but remains well behind challenger Sam Kaufman in overall campaign contributions, setting up a race defined by sharply contrasting donor bases.

Running from Jan. 1 to Mar. 30, 2026, Q1 is the first period in which all declared candidates have reported contributions together.

Henriquez reported $68,890 in Q1 contributions from 147 donors according to her campaign filing, eclipsing all candidates money-wise for the reporting period.

Kaufman, however, maintains a commanding financial lead, reporting $50,613.62 raised in Q1 and $115,245.42 total to date. During Q1 he logged 298 donors — the most of any candidate.

The split reflects a broader divide emerging in the race: Henriquez’s fundraising is anchored in a network of business owners, tourism operators and development-aligned interests, while Kaufman’s campaign is fueled by a high volume of individual donors, many of them retirees and residents tied to quality-of-life concerns.

Q1 Kaufman $1,000 Donations

Business/Corporate

• Padgett-Dekker Holdings

Individuals (Occupation)

• Bert Bender — Property Owner/Architect

• Judy Blume — Retired

• Frank Conrad — Sales

• David Dunn — Financial Advisor

• Kathleen Lash — Retired

• Francis Porter — Retired

• Renay Regardie — Retired

• Niel Ruchman — Retired

• Fred Schluter — Retired

• Joseph Trippi — Political Consultant

More than half of Kaufman’s 298 first-quarter donors, 55.4%, contributed less than $150, underscoring a grassroots-heavy funding base.

By contrast, Henriquez’s filing shows that of 147 donors, 54 businesses and business-affiliated individuals contributed at the $1,000 maximum, including entities such as Historic Tours–affiliated interests and Waste Management of Florida.

Both companies had matters pending before the mayor and City Commission after the donations were made, but prior to the Q1 donations being released.

HTA won several significant lease renewals and new contracts, tightening its grip on city-owned assets.

Waste Management was awarded a new contract increase at the expense of Key West residents, essentially paying more for fewer services.

Henriquez’s donor base was heavily concentrated among high-dollar contributors, with about 70% giving between $500 and $1,000, while roughly 28% of donors contributed less than $100 and about 2% fell in the middle tiers.

Of Henriquez’s $1,000 contributors, several currently sit on the Key West Chamber’s board of directors, including Amber Schaffer (president), John Toppino (first vice president), Casey Arnold (second vice president), George Fernandez and Suzanne Moore.

Q1 Henriquez $1,000 Donations

Businesses/Corporate

• 2537 Highway 27 LLC — Toppino

• Arnold’s Marine and Auto, Inc. — City towing contract

• Boone Mountain Paradise LLC — Robert Pabian

• Dane Black Consulting LLC — Construction

• Dave Black Consulting LLC — Construction

• Florida Keys Funeral Service — Peter E. Batty

• Gary’s Plumbing & Fire — Gary Centonze

• Hemingway House Museum

• Historic Properties Management Inc. — Historic Tours of America/Swift

• Key West Team Building — Casey Arnold

• Key West Theatre and Community Stage Inc.

• Lay Management LLC — Bill Lay

• Ocean Blue Galleries — Jay Schaffer

• Pabian Properties — Robert Pabian

• Rams Head Promotions of Key West LLC — Entertainment promotion

• Race World Offshore

• Rockland Recycling LLC — Toppino

• Sloans Landing — Swift/Batty

• Suncrest Mini-Self Storage

• The Conch House

• Waste Management of Florida — Greg Sullivan

• Wyland Galleries — Amber and Jay Schaffer

• Suzanne Moore Real Estate Services LLC — Suzanne Moore

Individuals (Occupation)

• Amy Lay — Executive, Catered Affairs Inc.

• Amber Schaffer — President, Key West Chamber of Commerce/Wyland Galleries

• Candace Atwell — A/P Manager

• Casey Arnold — GM, Conch Republic Seafood Company

• Darren Horan — Attorney, Horan Law

• Derek Epperly — Realtor, Engel & Völkers Key West

• Edwin O. Swift III — Tourism/Real Estate/Historic Tours of America

• Elizabeth Kehoe — Attorney, Oropeza, Stones, Cardenas

• Everett Atwell — Real Estate/Investments

• Freddy Varela — CFO, Historic Tours of America

• Gary Centonze — Business Owner, Gary the Plumber

• George Fernandez — Retired

• Jay Schaffer — Business Owner, Wyland Galleries/Ocean Blue

• Jessica Haim — Retail, Shaddow Fish/Tropically Hip

• John Toppino — Construction Industry, Toppino’s

• Joseph Farrell — Business Owner, Florida Straits Conch Company

• Mark Vasturo — Business Owner, Florida Straits Conch Company

• Natalie Machado — Accountant

• Patricia Gladding — Business Owner, Gary’s Plumbing

• Randy Kassewitz — Business Owner, Florida Straits Conch Company

• Randy Moore — CPA, Director, Spottswood Companies

• Robert Pabian — Pabian Properties/Boone Mountain Paradise LLC

• Robert Sharpe Jr. — Business Owner, CFO, Encore

• Robert Spottswood — Attorney/Executive Chairman, Spottswood Companies

• Sheri Varela — Retired

• Steve Henson — Business Owner, Key Iron Works

• Terry Lee Garcia — Realtor, Keller Williams Key West Compass Realty

• Timothy Atwell — Accountant

• Vianca Lay — Catering Director, Catered Affairs Inc.

Political Action Committee

• Dade County Police Benevolent Association

---

District Races Reflect Similar Patterns

From left, District II candidates Bobi Lore and former commissioner Mark Rossi.

District II

Bobi Lore reported $10,230.73 from 52 donors in Q1 fundraising.

Lore drew nearly 58% of his donors from contributions under $100, with about 35% giving between $100 and $500 and fewer than 8% at the $1,000 level.

Q1 Lore $1,000 Donations

Individuals (Occupation)

• Judy Blume — Retired

• George Cooper — Retired

• Melissa McDaniel — Retired

• Joe Trippi — Consultant

Opponent Mark Rossi reported $500 total from two donors, maintaining a self-imposed cap of $250 per donation.

---

From left, District IV candidates Sarah Compton, Juan Llera and Wayne Garcia.

District IV

Sarah Compton remained in the lead in overall fundraising in District IV, bringing in $14,989.21 across 77 donations placing her fourth in Q1 numbers.

Compton drew about 66% of her donors from contributions under $100, with roughly 29% between $100 and $500 and just over 5% exceeding that range.

Since filing to fill the District IV seat presumably being vacated by the embattled sitting commissioner Lissette Carey, Compton has raised $24,044.16.

Q1 Compton $1,000 Donations

Individuals (Occupation)

• Judy Blume — Retired

• Melissa McDaniel — Retired

• John Menefee — Retired

• Stephen Porter — Retired

• Kathleen Trippi — Retired

Her opponent, Juan Llera, reported $9,176.57 in Q1 but filed a waiver in Q4.

A majority of Llera’s donors contributed between $250 and $1,000, accounting for 50% of his donor base, including 22.7% between $250 and $500 and 27.3% at the $1,000 level, while 27.3% gave under $100 and 13.6% between $100 and $250. Most have ties to the business community or the Chamber of Commerce.

Q1 Llera $1,000 Donations

Businesses/Corporate

• Arnold’s Marine and Auto Repair

• Hemingway House

• Lay Management LLC — Bill Lay

• Waste Management of Florida

Individuals (Occupation)

• Edwin O. Swift III — Tourism/Real Estate/Historic Tours of America

Political Action Committee

• Dade County Police Benevolent Association

Candidate Wayne Garcia reported $200 in self-funding but recently entered the race.

---

From left, District V candidates Chris Massicotte and Greg Sullivan.

District V

Chris Massicotte reported $19,469.72 in Q1 fundraising from 94 donors, bringing his combined total to $36,448.20 to date.

The average donation was about $200, a clear sign that this campaign is fueled by residents chipping in what they can, not a handful of wealthy or well-connected insiders with contracts or business before the city.

Overall, Massicotte had the third-strongest showing in Q1 behind only Kaufman and Henriquez.

Q1 Massicotte $1,000 Donations

Businesses/Corporate

• Padgett-Dekker Holdings

Individuals (Occupation)

• Judy Blume — Retired

• Carol DeFord — Retired

• Anthony Falcone — Retired

• Bryan Green — Retired

• Melissa McDaniel — Retired

• William McGurn III — Retired

• Joe Trippi — Political Consultant

Opponent Greg Sullivan, who is also the senior district manager for Waste Management of Florida, reported $3,100, including three $1,000 contributions from business-aligned donors. In addition, Sullivan contributed $100 to his campaign. In contrast to the other candidates, that is a mix of 75% big donors with 25% coming from self-funding — a pattern that is likely to continue given his prominent role in the Chamber and business community.

He did not garner the same $1,000 donoation from Waste Management as Llera and Henriquez. It is unclear whether the company believes that would be a conflict of interest or he began compaigning too late.

Q1 Sullivan $1,000 Donations

Businesses/Corporate

• Arnold’s Marine and Auto Repair

• Hemingway House

Individuals (Occupation)

• Gary Centonze — Business Owner, Gary’s Plumbing and Fire

---

Competing Coalitions

The early fundraising data points to a political dichotomy shaping the mayoral race.

On one side is a coalition aligned with the city’s business community and Chamber of Commerce membership directory. On the other is a donor base more heavily composed of residents focused on water quality, government transparency, fiscal responsibility and quality of life.

The early numbers suggest the 2026 races may be defined as much by donor coalitions as by candidates themselves.

Second-quarter campaign finance reports, covering April through June, are due July 10 under Florida law, the final quarterly filing before candidates transition to more frequent pre-election biweekly disclosures.

This is an evolving story. Watch this space for more indepth coverage of the 2026 election cycle.

---