District 2 City Commission Seat Draws Two Candidates

With Commissioner Sam Kaufman launching a mayoral bid, his District 2 seat will be open in the 2026 election. Two longtime Key West business owners have stepped forward, one with political experience and deep Key West roots, and the other a newcomer to Key West without political experience.

Bobi Lore, owner of the men only guest house called the Island House, has officially announced his candidacy. On his campaign site, Lore describes himself as a “business owner and local activist” committed to transparency, open debate, and standing for the working people who keep the island running. He pledges regular constituent meetings and rejects “backroom deals,” emphasizing integrity and the common good.

Island House, on Fleming Street, promotes itself as one of the last gay clothing-optional resorts in Old Town. It has a swimming pool, bar, drag shows, a special "video room" open all night, and a restaurant.

Mark Rossi, former District 2 commissioner (2005–2015) and owner of the Rick’s/Durty Harry’s entertainment complex, says he is also running for the seat. Rossi frames his campaign around “proven leadership,” citing his prior service and pledging to fix streets, address the hospital contract, and support the military.

Rick’s Bar is a complex with themed areas ranging from a lounge to a dance club to live music. It’s part of the larger Rick’s & Durty Harry’s Entertainment Complex, located on Duval Street. It’s considered one of the largest drinking establishments in the Florida Keys, featuring eight distinct bars under one roof.

The last primary in Monroe County, which included some City Commission elections, was in August 2024 and had a low turnout of only 28%. Voters still have time to improve that turnout. The next primary is in August 2026 and the general election is in November 2026. Voter information and online voter registration can be found here.