Two of the three Key West City Commission races were decided in the Aug. 18 election, while one race will head to a November runoff.
After a week of discussions about delayed election results due to the removal of landlines and fax capability from the county’s 33 polling places, it turns out all results countywide were known by 9:25 p.m. less than two and a half hours after the polls closed.
The Key West race results were published online around 8:30 p.m.
In those Key West races, Mark Rossi reclaimed the District II city commission seat being vacated by mayor-elect Sam Kaufman, who handily defeated incumbent Mayor Dee Dee Henriquez this week. Rossi represented District II about 10 years ago and this week bested candidate Bobi Lore to return to it. The District II race drew only 462 voters to the polls, but Rossi earned 50 more votes than Lore.
While the city races are officially nonpartisan, Rossi is the only Republican who won a Key West race.
In District V, Chris Massicotte will take the seat that until earlier this month was occupied by Greg Veliz, who was appointed to complete the term of the late commissioner Mary Lou Hoover, who died in November 2025 while in office.
Massicotte defeated Greg Sullivan by a significant margin, 57% to 43%.
Rossi and Massicotte, along with Kaufman, will be sworn in at noon on Friday, Aug. 28 at city hall.
The District IV seat will remain a question mark, as it heads to a Nov. 3 runoff between Sarah Compton and Wayne Garcia, both Democrats. Incumbent commissioner Lissette Carey will remain in place representing District IV until that runoff identifies a winner.
The Aug. 18 election wrapped up several months of vicious attacks against Massicotte, mostly, with Kaufman and Compton drawing fire as well from one particularly combative local business owner.
The online attacks drew the attention of Todd German, president of the nonprofit Hometown organization, a nonpartisan voter education group. German asked Massicotte about the smear campaign
“You had people whose hobby in life was to tear you apart,” German said on election night. “Any thoughts on all that, particularly thinking about prospective candidates in the future that will have to go through what you went through?”
Massicotte replied, “I’m going to do my best to let bygones be bygones, but it’s very hard because I’ve never seen someone do that. I’ve been in professional politics for 20 years and I’ve never seen someone go that far to try to tear down an individual candidate. I don’t know what his motivation was other than he wanted me to lose. But the tactics he used, and the tactics that the other PAC used against (Sam Kaufman) also weren’t effective.”
Massicotte then pointed out that polling conducted in April by the slate of aligned Democrats in the city races found that “after affordability in housing, corruption was the No. 2 issue that concerned Key West voters.”
Full election results are available at votemonroeflkeys.gov.
Key West City Commission results (Winners’ names in bold.)
District II
Bobi Lore — 45% | 206 votes
Mark Rossi — 55% | 256 votes
District IV – (To be decided in a November runoff.)
Sarah Compton — 42% | 623 votes
Wayne Garcia — 34% | 493 votes
Juan Llera — 24% | 350 votes
District V
Chris Massicotte — 57% | 710 votes
Greg Sullivan — 43% | 535 votes
