The Ballot Brief
Monroe County, Florida

Key West City Commission, District V

Florida › Monroe County › Key West City Commission, District V

Decided at the 2026 primary: Chris Massicotte won the seat

August 18 result: Chris Massicotte won outright with 57.02 percent over Gregory Sullivan, per the Supervisor of Elections' official results, for this open seat after appointed interim Commissioner Greg Veliz did not file; this nonpartisan race will not appear on the November 3 ballot.

Winner

Chris Massicotte

Nonpartisan

Biography
Chris Massicotte is a community leader and former political consultant who serves as president of Keys Last Stand, per his campaign site. He moved to Key West in 2017 and has advocated for smarter growth and environmental protection, per the same source.
Top Priorities
  • Push for clear, accountable decision-making at City Hall
  • Support affordable housing and infrastructure investment
  • Protect water quality and the character of the island
Per the campaign site.
Per the candidate campaign site, roster verified 2026-09-12.
Campaign site

Also ran in the primary

Gregory Sullivan

Nonpartisan

Profile
Biography
Greg Sullivan is the senior district manager for WM (Waste Management), which handles Key West's trash and recycling collection, per city and local coverage. He has served on the Key West Chamber of Commerce board, per the same coverage.
Top Priorities
  • Expand the city's youth summer employment program
  • Focus on practical maintenance that improves everyday city services
Per the campaign coverage (per web search summary).
Campaign site

Questions about this race

Who is running for Key West City Commission, District V in 2026?

The Key West City Commission, District V race was decided at the 2026 primary - Chris Massicotte won the seat - and does not appear on the November 3, 2026 ballot. 2 candidates were on the primary ballot: Chris Massicotte and Gregory Sullivan. Candidate information follows official Monroe County election filings; verify with the official election office linked below.

When is the Key West City Commission, District V election in Florida?

Election Day is Tuesday, November 3, 2026. Registration deadlines, early voting dates and mail ballot rules for Florida are on the Florida election hub at theballotbrief.com.

How do I see my exact Monroe County ballot?

Enter your ZIP code in the lookup at theballotbrief.com for the statewide and congressional races, or a full street address to add the county, city and district contests for that location.

Sources
Verify this race
Candidate roster from official Monroe County Supervisor of Elections filings, last verified 2026-09-12. Bios and priorities carry their attribution inline.
Cross-check with the official Florida election office, or see the full Monroe County sample ballot and your exact ballot by address.