The Future of Key West 2026 Elections: Turnout and Tension

By: Liana Gonzalez-Blanco Novermber 29, 2026

Key West politics reveal a striking contrast between uncontested victories and hard-fought campaigns. Nearly 30% of city leadership entered office without voter input, while other races—like Commissioner Lissette Carey’s—showed how turnout and credibility can decide outcomes. As the 2026 elections approach, Mayor DeeDee Henriquez faces her first real challenge against Commissioner Sam Kaufman, setting up a contest that highlights the island’s deep divide between liberal newcomers and conservative locals. With housing, tourism, and affordability on the line, Key West’s future identity will be shaped at the ballot box.

The Future of Key West 2026 Elections: Turnout and Tension

Key West’s leadership has seen some unusual dynamics in recent years. Mayor DeeDee Henriquez stepped into office in 2024 without a single vote cast, since she had no challengers. The same was true for Commissioner Donnie Lee in District 3, who also filled his seat unopposed. That means nearly 30% of the city’s leadership holds office without direct voter representation. The rest of the dais, however, tells a different story.

Commissioner Lissette Carey earned her District 4 seat in a hard-fought election. When Greg Davila chose not to run again in 2022, the race became one of the most crowded in recent memory, with four candidates vying for the spot. Carey and Kim Highsmith advanced past the primary, but Highsmith’s arrest in a domestic abuse case destroyed her credibility, and Carey ultimately won the general election. Carey stood out as the only Key West native and Republican in the race. 

The other candidates included a Coral Shores High School graduate with businesses across the Keys, a service industry worker, and Highsmith, a recent transplant who ran as the clear liberal. Today, District 4 is again in flux, with newcomers Sarah Compton from Missouri and Jesus Llera from Miami announcing their candidacies. The district is experiencing an identity crisis, with liberal voters backing newcomers who support policies like rainbow crosswalks, while conservative voters tend to favor natives who emphasize law and order and family safety.

The numbers from 2022 highlight how much turnout matters. In the primary, only 34% of voters participated countywide—just 18,700 out of 54,700 registered voters. That meant only 1,351 votes decided who advanced to the general. Despite the ease of voting from home, turnout was abysmal. The general election was stronger, with turnout jumping to 62%. Carey won her seat with 1,750 votes, while Republicans across the ballot—Mooney, Patronis, Moody, Rubio, Gimenez, and DeSantis—carried Monroe County by 20 points, signaling a red wave. That momentum grew even larger in the 2024 presidential election. In contrast, Lee and Henriquez did no campaigning and walked into their seats unchallenged.

Lee’s background as a lifelong Key West resident and former Chief of Police gave him credibility, but his uncontested victory in 2024 meant voters never weighed in. Henriquez, who served as Monroe County Tax Collector for two decades, raised over $51,000 for her mayoral campaign but also ran unopposed. Both represent the pattern of uncontested races in Key West, where established locals often secure leadership without competition. Yet when they cast votes in favor of liberal policies, conservative residents grow uneasy. The old assumption that being a local meant supporting the community no longer holds. Most of the City Commission Key West locals voted this year for immigration and rainbow crosswalk policies that were against safety for the community.  

Heading into 2026, candidates will need more than name recognition. Voters expect clear answers about housing, tourism, and affordability. Platitudes about transparency or fiscal responsibility won’t cut it. Without specifics, turnout could sink again.

The 2026 mayoral race will be especially telling. Mayor Henriquez will finally have to campaign, facing Commissioner Sam Kaufman, who has a decade of electoral victories behind him. Kaufman’s liberal district supports him strongly, but he’ll need votes citywide to win. His platform may resonate downtown, but in conservative midtown neighborhoods, Henriquez could hold an edge. Her challenge will be explaining her support for policies conservatives dislike, such as opposing ICE cooperation and backing rainbow crosswalks. The race will expose the divide between Key West’s liberal and conservative factions. Liberals have Henriquez as their champion, while conservatives are still searching for a leader who won’t try to placate both sides.

Kaufman’s own record shows why he’s a serious contender. Since 2015, he has won three straight elections in District 2. He first defeated former mayor Morgan McPherson with 62.5% of the vote, then beat attorney Robert Carr in 2018, and in 2022 won decisively against businessman Leslie “Les” Green with 1,438 votes (63%) to Green’s 838 (37%). His track record demonstrates consistent voter trust and sets the stage for his mayoral run in 2026. Meanwhile, District 2 will see its own battle, with longtime insider Mark Rossi, a bar complex owner and former commissioner, facing newcomer Bobi Lore, a guesthouse owner and activist. Their contest is the classic insider-versus-outsider matchup, and voters are demanding specifics. The stakes in 2026 are high. 

No one will skate into office this time, whether liberal or conservative. Residents feel the weight of every decision, as policies directly affect their daily lives. With tourism reshaping the island and new residents arriving from expensive liberal cities to more affordable Florida, Key West is caught in a clash of ideas. The District 2 race, and the mayoral contest, will help decide which vision defines the island’s future. Whoever wins won’t just hold office—they’ll shape the identity of Key West, a diamond in the rough, formed under pressure, waiting to shine.

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Liana Gonzalez-Blanco

Liana is a Key West native who loves writing about her island home. She taught English to students in grades 6–12 for nearly 35 years in Key West schools, sharing her love of literature and language with generations of local students. She earned a bachelor’s degree in English from the University of Florida and a master’s degree in Educational Leadership from the University of Central Florida. Liana is the owner of Conch Media Group, LLC, and the creator and manager of The Key West Post. Her goal is to keep readers informed about the issues that matter most in Key West. As a lifelong local, she offers a perspective often missing from corporate media and from journalists and bloggers who are new to the island.  When Liana isn't writing and managing this website, she enjoys spending time with her friends and family. On most days, you’ll find her walking, biking, or running outdoors, soaking up the natural beauty, friendly people, and diverse cultures that make Key West so special.

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