It’s election season in Key West, so battle lines are drawn — and checkbooks are out.

On Aug. 18, Key West voters will elect a mayor and city commissioners in Districts II, IV and V. As of April 15, no incumbents had filed to run in any of the three city commission races.

But with three candidates running in District IV — Sarah Compton, Wayne Garcia and Juan Llera — if no candidate secures more than 50% of the vote on Aug. 18, then the top two vote-getters in that race will proceed to a run-off election on Nov. 3. 

In the mayor’s race, Mayor Dee Dee Henriquez, who ran unopposed for her first term two years ago, now faces City Commissioner Sam Kaufman in a contentious and expensive contest.

While all Key West voters elect the mayor, only voters in Districts II, IV and V will elect their commissioners. 

Candidates were required to file their latest financial statements on April 10, listing monetary and in-kind contributions received by their campaigns between Jan. 1 and March 31, as well as campaign expenditures.

The mayor’s race, by far, has drawn the most financial attention. Henriquez’s campaign had raised $68,890 as of March 31, while Kaufman’s campaign had raised $115,245 as of the same date.

Here is a closer look at the support each candidate has received and from which sectors of the community.

MAYOR

Dee Dee Henriquez (incumbent): $68,890

Sam Kaufman: $115,245

Danise “Dee Dee” Henriquez

Henriquez has received donations from many prominent and influential Conch families and business leaders in town, including the Spottswoods, Ed Swift, Peter E. Batty, Sam Holland, Freddy Varela, former city attorney Shawn Smith, Arnold’s Towing, Jason and Gregory Barroso, who are city officials and brothers of the city manager Brian L. Barroso. The incumbent has also received donations from Waste Management Inc., which employs District V candidate Greg Sullivan. Key West Theater, Rams Head, Gary’s Plumbing, Penny Walker, Daniel Sujak, Wyland Galleries, Ocean Blue Galleries, restaurateur Bill Lay and Lay Management Co. 

“My campaign is supported by a wide range of Key West residents, including young generations, working families, retirees, longtime residents and local business owners,” Henriquez told the Keys Weekly. “Our supporters share a commitment to keeping Key West moving forward, including local business owners who employ hundreds of families in our community. Those businesses are essential to our local economy and help sustain working families across Key West. Voters can see the difference between political spin and real leadership.”

Sam Kaufman

Kaufman has received contributions from prominent donors including author Judy Blume, architect Bert Bender, philanthropist John Padget, David Dunn, JR Fogarty, Misohappy Sushi restaurant, Barbara and Evan Corns, Lynn Kaufelt, JT Thompson (who founded Key West’s  One Human Family campaign) and Arlo Haskell, who led the Safer Cleaner Ships initiative against large cruise ships in 2020, and whose mother, Monica Haskell, is the current District I city commissioner. 

“The strength of this campaign is the people behind it,” Kaufman said in a press release issued following the latest financial disclosure deadline. “This campaign is built on local support, local voices, and a shared commitment to improving our city. We are focused on honest government, transparency, and making decisions that reflect the priorities of our community.

“The vast majority of contributions have come from local residents, underscoring the campaign’s grassroots foundation and strong connection to Key West voters,” the release states.

CITY COMMISSION, DISTRICT II 

Bobi Lore: $10,750

Mark Rossi:  $450

Bobi Lore

In District II, Bobi Lore entered the race significantly earlier than Mark Rossi, who held the District II seat before Kaufman, who must resign this summer given his mayoral campaign. 

Lore has received campaign donations from Blume and her husband, George Cooper, as well as an in-kind donation of a photography shoot by Key West’s Nick Doll. He has also received donations from Melissa McDaniel, Lynn Kaufelt, Brian Robinson, Wayne Smith and others. 

On his campaign website, Lore describes himself as “a Key West business owner and local activist” who will “stand for the working people of this community, who bear the weight of keeping our island functioning at its best, with integrity and genuine care for their well being.”

Mark Rossi

Having entered the race more recently, Rossi has received donations from attorney Ron Solomon and from the corporation that owns the Ernest Hemingway Home & Museum.

Rossi summed up his campaign in two words at a candidate event last month.

“Proven leadership,” he said, pointing to his prior tenure as the District II commissioner, from 2005 to 2015, when he stepped down and Kaufman won an election for the commission seat, which he still holds.

CITY COMMISSION, DISTRICT IV

Sarah Compton: $24,044

Wayne Garcia: $200

Juan Llera: $9,176

Sarah Compton

In District IV, Sarah Compton has been campaigning significantly longer than her opponents, as Garcia just entered the race a month ago.

Compton has received donations of $500 and $1,000 from Blume, Phil Amsterdam, Barbara Corns, Fred Covan, health care advocate Spencer Krenke and McDaniel. Compton’s campaign also has received scores of smaller donations in $25 and $50 increments. 

“In the most recent Campaign Treasurer’s Report, about 85% of the contributions originated from supporters in Key West with an average of $160 per donation,” states a release from Compton’s campaign. “These are small business owners, service industry workers, neighbors, people who live here, work here, and are ready for something better.

“It tells me people are paying attention,” Compton said. “They’re engaged. And they want a city government that actually works for them.”The support comes at a time when a lot of people feel frustrated and shut out of the process. Instead of checking out, this community is leaning in.”

Wayne Garcia

The most recent entry into the District II race, contractor and artist Wayne Garcia, has thus far seeded his campaign with $200 of his own money.

“Having lived in District 4 for more than 35 years, I understand the challenges our residents face,” Garcia said in a statement. “My top priorities include the cleanup and revitalization of Riviera Canal, improving sidewalk accessibility throughout District 4 by repairing and installing new sidewalks, addressing local flooding issues and developing a thoughtful plan for Little Hamaca Park.”

He added that he believes Key West must ensure all of its employees are paid a living wage that reflects the true cost of living in the city.

“I’m running for city commissioner to bring integrity to the commission, restore a sense of pride in our community and uphold a commitment to honest, transparent government,” Garcia said.

Juan Llera

Navy combat veteran, former law enforcement officer and current Keys Energy Services director, Juan Llera has received $500 or $1,000 donations from Arnold’s Towing, Penny Phelps, Dade County PDA political action committee, Waste Management, Bruce Guerdan, Darren Horan, Lay Management Co. and Swift. He also received an endorsement from the South Florida Police Benevolent Association.

“Our city commission deserves leadership that listens, shows up and gets results,” Llera said in a social media statement about his campaign. “I’m running to make our city safer, stronger and more connected, but I can’t do it alone.”

DISTRICT V, CITY COMMISSION

Chris Massicotte: $36,448

Greg Sullivan: $3,100

Chris Massicotte

In District V, Chris Massicotte entered the race significantly earlier than his opponent, Greg Sullivan, who just announced his candidacy in early March. 

Massicotte’s campaign donors include many of the same people who have donated to Kaufman and Compton, with $500 and $1,000 donations coming to Massicotte from Blume, the Cornses, Dunn. Other donations are from Carol Deford, Bryan Green, commissioner Haskell, Kaufelt, Linda Mewshaw, Padget, Smith, Doll (who donated a photography shoot as an in-kind service) and Tony Falcone. 

His campaign also has received scores of smaller donations. 

“More than two dozen contributors are District V voters, the very people who will decide this election,” Massicotte said in a press release. “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.

“Massicotte has also pledged not to accept contributions from anyone who has or is seeking contracts or leases with the City of Key West, reinforcing his commitment to independence and accountability,” the release states.

Greg Sullivan

Greg Sullivan is the senior regional manager of WM, formerly known as Waste Management Inc., which handles the city’s trash and recycling collection.

He entered the District V race in early March and has received $1,000 donations from Arnold’s Towing, Gary Centonze of Gary’s Plumbing and the corporation that owns the Ernest Hemingway Home & Museum. 

Sullivan told the Keys Weekly last month, “I want to bring good, common sense to Key West and get things done. I’ve been here 31 years. I’ve never missed a hurricane and I think I understand what Key West residents need and want. I’m a nuts and bolts guy. I want to get things done, not postpone things. I’m all about maintenance and doing things that will make everyday life better for the people of Key West.”