Two Key West Business Owners Enter District Two Commission Race
On November 11, two longtime Key West business owners announced campaigns for the District 2 city commission seat, setting up a contest focused on transparency, infrastructure, and local services. The developments matter to residents because the vacancy was created by an incumbent commissioner launching a mayoral bid, and the outcome will shape policy on streets, healthcare contracts, and support for working households.
Two prominent local business owners filed campaign announcements on November 11 for Key West City Commission District 2, signaling a contested race for a seat that opened after an incumbent city commissioner announced a run for mayor. The candidates are Bobi Lore, owner of the Island House guest house, and Mark Rossi, owner of the Rick's and Durty Harry's entertainment complex and a former District 2 commissioner.
Both candidates framed their campaigns around issues that resonate with a broad range of voters. Lore positioned his bid around greater transparency in local government, improved access for constituents to city leadership, and advocacy for working residents who face rising costs in the Florida Keys. Rossi emphasized his prior city government experience and outlined a platform that prioritizes street repairs, scrutiny of healthcare contracts, and continued support for the military community that contributes to Key West's economy and identity.
The announcements included campaign websites and public statements from each candidate outlining priorities and qualifications. With an open seat on the commission, the contest raises questions about continuity of policy and the balance of institutional knowledge on the commission. Rossi’s experience as a former commissioner offers voters a known quantity in governance and familiarity with municipal procedures. Lore’s background as a hospitality business owner presents a perspective grounded in the day to day needs of working residents and small enterprises that drive local tourism and employment.
The timing of these filings follows the procedural steps required in the municipal election calendar. Candidates must complete official campaign filings to qualify for the ballot, and the city will schedule a primary and any subsequent runoff consistent with established election rules. Those procedural milestones will determine the timeline for debates, candidate forums, and voter engagement activities ahead of the general municipal election.
For Monroe County residents, the race will have concrete implications. Decisions on street maintenance affect commute safety and tourism traffic. Outcomes of healthcare contract reviews can influence access and cost for municipal employees and vulnerable residents. And city policy toward military installations and service members can have economic and social consequences for neighborhoods that host service families.
The contest also offers an opportunity to assess how well local institutions respond to competing priorities, and how accessible elected officials remain to residents. Voters will weigh experience against fresh perspectives as the campaign moves into the formal filing period and the city schedules primary dates. Civic participation during that window will shape the commission that determines key municipal services and the allocation of limited public resources in Key West.
