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Key West Elects First Jewish Mayor in Nearly 200-Year History

Summary
Key West, Florida, has elected its first Jewish mayor in the city’s nearly two centuries of history, with longtime city commissioner and attorney Samuel Kaufman defeating incumbent Mayor Dee Dee Henriquez in Tuesday’s election. Kaufman told JNS that the historic nature of his election carries particular meaning for him, especially given the role Jews have played in the island community over the years. “To carry that forward and to contribute in a positive way to the entire city as a Jewish person, given our values and given what it means to me to be a Jewish person, it’s an incredible honor and responsibility,” Kaufman said. “It gives me incredible pride to be that first Jewish mayor.” Although the mayor’s office in Key West is officially nonpartisan, Kaufman is a Democrat, while Henriquez is a Republican. Kaufman captured approximately 58% of the vote, compared with 42% for the incumbent.
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Key West Elects First Jewish Mayor in Nearly 200-Year History

Key West, Florida, has elected its first Jewish mayor in the city’s nearly two centuries of history, with longtime city commissioner and attorney Samuel Kaufman defeating incumbent Mayor Dee Dee Henriquez in Tuesday’s election. Kaufman told JNS that the historic nature of his election carries particular meaning for him, especially given the role Jews have played in the island community over the years. “To carry that forward and to contribute in a positive way to the entire city as a Jewish person, given our values and given what it means to me to be a Jewish person, it’s an incredible honor and responsibility,” Kaufman said. “It gives me incredible pride to be that first Jewish mayor.” Although the mayor’s office in Key West is officially nonpartisan, Kaufman is a Democrat, while Henriquez is a Republican. Kaufman captured approximately 58% of the vote, compared with 42% for the incumbent. Born in New York City, Kaufman has spent the past three decades building his professional career in Key West. He said his victory included support from Republican voters who crossed party lines following a major corruption controversy that rocked the incumbent city administration. “We had a really huge corruption scandal,” Kaufman told JNS. “Our city attorney, our city building official and our city code enforcement director were all taken out in handcuffs.” Three officials connected to the administration were charged with felonies involving evidence tampering in 2025, a development that Kaufman said played a role in the political environment surrounding this year’s election. Key West, the largest municipality in the Florida Keys, has approximately 25,000 permanent residents. Kaufman estimates that roughly 1,000 members of the city’s population are Jewish. The city’s population, however, swells dramatically because of tourism. Key West estimates that approximately 3 million visitors arrive each year, and the impact of that enormous tourist presence emerged as a major concern for residents during the mayoral race. “We don’t want five cruise ships a day,” Kaufman said. “We can’t accommodate that. We don’t have the infrastructure for that.” “We like one cruise ship a day, on my side of the political scale,” he told JNS. “Others may want three or four ships a day.” Politically, Kaufman characterized Key West as a “liberal blue” enclave within the more conservative Monroe County. Despite its liberal political leanings, he said the city has largely avoided the anti-Israel activism that has surfaced in some other progressive communities. Kaufman attributed that in part to Key West’s ties to its Jewish population and to the significant number of Israelis with connections to the city. “You won’t see Palestinian flags ever in the city,” Kaufman told JNS. “The same week as Oct. 7, I sponsored a resolution, and it was unanimously approved by our city commission, condemning the terrorist attack and supporting the State of Israel.” Kaufman said the city went even further by displaying the Israeli flag outside City Hall following the Oct. 7 terrorist attack. “As a result of that we’re probably the only city in the state and in the country that raised the Israeli flag on our City Hall, next to our state flag, next to the American flag,” he said. “It stayed there for four months.” Kaufman describes himself as a “somewhat observant” Jew and said he davens at the local Chabad. With his election victory coming shortly before the High Holidays, the mayor-elect said he is especially looking forward to celebrating the upcoming Yomim Tovim with the local Jewish community. “It’s going to be a bigger party than ever,” he said. “People should feel excited about going to such a special place like Key West.” “We’re an inclusive place that will even elect a Jewish mayor,” Kaufman said. {Matzav.com}

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matzav.com broke the news on Sunday, August 23, 2026.
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