Open Key West Commission Seat Draws Two Local Business Candidates
With Commissioner Sam Kaufman launching a mayoral campaign on November 13, 2025, his District 2 Key West city commission seat became open, and two local business owners filed to run. Their candidacies foreground transparency, infrastructure and hospital contract issues, matters that directly affect residents, businesses and public services ahead of the 2026 elections.
Commissioner Sam Kaufman’s entry into the mayoral race on November 13, 2025 opened a consequential contest for Key West City Commission District 2, prompting two locally known business owners to file for the seat. The filings set up a campaign season that will play out through the August 2026 primary and the November 2026 general election.
Bobi Lore filed as a candidate for District 2 while identifying himself as the owner of the Island House guesthouse. The filing described him as a business owner and local activist who intends to hold regular constituent meetings and push for greater transparency in local government. Lore’s appeal will likely focus on community outreach and accountability to voters in a district attentive to small business concerns and tourism economy impacts.
Mark Rossi also filed for the District 2 seat. Rossi served on the commission from 2005 to 2015 and is the owner of the Rick’s slash Durty Harry’s entertainment complex on Duval Street. His campaign framed itself around "proven leadership" and emphasized infrastructure priorities and oversight of a pending hospital contract as central issues for the district. Rossi’s tenure on the commission and business profile signal a campaign built on governing experience and sector specific knowledge of downtown commerce.
The vacancy created by Kaufman’s mayoral bid transforms an internal succession into a contested electoral test at a time when local policy questions are salient. Infrastructure investment and the municipal approach to the hospital contract carry direct budgetary and service delivery implications for Monroe County residents. The presence of two business owners in the race underscores the intersection of commercial interests and municipal governance in Key West.
Voter engagement and turnout patterns will matter for the outcome, with the August 2026 primary determining which candidates move on to the November general election. Residents should expect a campaign centered on constituent outreach, economic considerations tied to Duval Street commerce, and the commission’s role in contracting and infrastructure decisions that shape daily life in Key West.
