District 4 City Commission Race Heats Up
- Nov 19
- 5 min read
Updated: 4 days ago
The "One Human Family" has two distinct communities in Key West, and District 4 in the center of the island is a perfect example of the differences.
District 4 City Commission Race Heat Up
Key West now has a third candidate running for the District 4 City Commissioner seat. Juan Llera, born in Cuba, and Sarah Compton from Missouri, are two outsiders hoping to lead District 4 residents in Key West. Commissioner Lissette Carey, a Key West native, has yet to announce a re-election bid. The deadline to qualify and officially announce is June 17–21, 2026.
Llera and Compton have announced very early and Commissioner Carey still has time to announce her intentions. Elections reflect the values of a community, and District 4 leans conservative, but that could change next year. Voters will choose between a Key West native with a proven conservative voting record, or two newcomers without prior political experience or voting records. The pros and cons for each depends on which voters you ask, liberal or conservative.
Juan Llera served in the Navy and law enforcement in Miami. He now works for Keys Energy in the Safety and Risk Department for about three years. His views on policy are unknown, but he does want to "establish trust" in city government and voters will have to ask what that means for them. It is unknown where he stands on issues like immigration or rainbow crosswalks, two issues which exploded in controversy and national attention in Key West. Of all the candidates in District 4, he is the only one with no publicly stated opinions about any issues in Key West, but that could change as he faces voter questions.
Commissioner Carey is the only person on the City Commission with a strong conservative voting record. For example, she was the only one to support immigration laws in Key West. She even stated in a Fox News interview that she was "shocked to stand alone." Attorney General James Uthmeier, in a letter to the commissioners, said their vote (excluding Carey) violates state law and has essentially made Key West a "sanctuary city." After a national humiliation and a strongly worded letter by Attorney General Uthmeier, Mayor Henriquez and the other City Commissioners-Lee, Hoover, Castillo, and Haskell- reversed their votes against 287g agreement with ICE. This agreement allowed the KWPD to coordinate with ICE to remove criminal illegal immigrants from the community. Under threat of removal by Governor Desantis for opposing ICE and federal laws, the others later joined Carey to vote in support of the agreement and the safety of Key West.
However, Commissioner Kauffmen, who just announced his run for Mayor, avoided the controversial vote by not attending the meeting via Zoom, like other Commissioners do when they can't attend in person. He claimed to not have internet service, even though he emailed the city from his vacation location, just an hour prior to the meeting. Mayor Henriquez pointed out this fact during the televised meeting. His prior vote and public comments against ICE, indicate he would have voted against the 287g agreement. As the only vote in support of following the law, Commissioner Carey proved she is not afraid to vote on principle, even if she is the only one doing so. Her possible future opponents, if she declares a re-election bid, will serve as a sharp contrast to her conservative positions.
On the opposite end of the political spectrum, Sarah Compton has taken positions that set her apart in District 4. She has strongly opposed cooperation with ICE in removing criminal illegal immigrants from Key West and was active with a local open-borders group. Compton also supports defying state law regarding rainbow crosswalks, an issue that liberal groups in Key West fought for but ultimately lost. Her positions have earned her backing from the liberal contingent in District 4. She works in the hospitality industry in Key West.
This same group attempted to remove Commissioner Lissette Carey from office after she was mentioned in a Grand Jury report, despite no charges being filed against her. Believing that the mere mention was grounds for removal, the liberal group in her district launched a recall effort. However, the initiative quickly faltered.
The recall lacked sufficient support within District 4 and faced credibility issues. One affidavit from a resident stated she was given false information about the petition’s purpose and pressured to sign before asking questions. Ultimately, Supervisor of Elections Sherri Hodies denied the recall petition, ruling that it failed to comply with state law. Legal deadlines were missed, and concerns about illegal funding and organizational practices dealt the final blow to an already weak effort.
The irony is clear: a group seeking to remove an elected official without evidence of wrongdoing was itself stopped for breaking the law.
Meanwhile, Commissioner Carey has not yet announced whether she will seek re-election. She has until June 2026 to decide. The primary election is scheduled for August 2026, followed by the general election in November 2026.
While Commissioner Lee and Mayor Henriquez filled their positions without challengers or elections, District 4 in the center of Key West remains one of the island’s most politically active — and most controversial — seats.
The last election for District 4 in 2022 was a classic showdown between a conservative local and a liberal newcomer. However, candidate Kim Highsmith faced intense scrutiny after being arrested for domestic violence during her campaign.
According to a local newspaper, Kim Highsmith told police that on the night of Sunday, September 18th, that she and her husband, Bobby Highsmith, a current school board member at the time, were having a verbal argument. The stepson told police that both Kim and Bobby Highsmith were intoxicated at the time of the argument, which continued into Monday morning, Sept. 19. At one point the stepson intervened in the argument and admitted to throwing water on Kim Highsmith, who told police she had defended herself. She admitted giving her stepson scratches on his neck during the altercation.
Kim Highsmith told police her relationship with her stepson is “volatile” and sometimes “aggressive.” Although no charges were ultimately filed, voters appeared to question her ability to lead District 4. She went on to lose the runoff election to Commissioner Lissette Carey, showing that having a mug shot taken in the middle of a campaign election, rarely works to one's benefit, unless of course your name is Donald Trump.
Looking ahead to the August 2026 primary, District 4 voters may once again face a choice between conservative and liberal candidates, if Carey decides to run. The race highlights two distinct communities in Key West.
Key West has Liberal-leaning voters who favor policies such as immigration leniency for illegal immigrants and keeping rainbow crosswalks. They prefer no involvement from state and federal authorities, seeking to implement their own progressive agendas locally, even when those initiatives conflict with state and federal laws.
The other group of voters in Key West is the Conservative-leaning voters, who want law and order and support leaders who follow common sense laws. They backed the signing of 287(g) agreements between the Key West Police Department and ICE, advocating for the removal of criminal illegal immigrants. They also supported removing rainbow crosswalks, citing compliance with state law and roadway safety.
District 4 mirrors the broader tension seen at both the state and national levels between liberal and conservative priorities. According to Supervisor of Elections data, registered Republicans in Monroe County outnumber Democrats by at least 10,000 voters. The county demonstrated strong conservative support in the 2024 election, voting overwhelmingly for Republican candidates. Whether this “Red Wave” will carry into District 4 remains to be seen. Voters will have their say in the August 2026 primary and again in the November 2026 general election.
Get more election information and register to vote at the Monroe County Supervisor of Elections website here.
