Sullivan Outraises Massicotte in Latest Key West District V Fundraising Period
District V challenger posts stronger spring fundraising haul, while Massicotte maintains overall cash advantage.
KEY WEST — Waste Management’s Greg Sullivan significantly outraised fellow District V City Commission candidate Chris Massicotte during the latest campaign finance reporting period, according to reports filed with the city.
Sullivan reported raising $27,183.50 in monetary contributions between April 1 and May 31, compared with $7,301.04 raised by Massicotte during the same period. Sullivan also reported $2,977.05 in in-kind contributions.
Through May 31, Sullivan had raised $30,283.50 in total monetary contributions since entering the race, while Massicotte extended his lead to $43,749.24 in cumulative fundraising.
The reports show a race with contrasting fundraising trends. While Massicotte retains the overall fundraising lead, Sullivan posted the stronger performance during the spring reporting period, bringing in nearly four times as much money as his opponent.
Among Sullivan’s notable contributors were several prominent Key West business owners and tourism-related interests — all heavily aligned with the Chamber of Commercce. Contributors giving $1,000 or more included Edwin O. Swift, Wyland Galleries, Lay Management, Ocean Blue Galleries, Gary’s Plumbing & Fire, Spottswood Management Inc., Next Chapter Fishing Charters, The LKT Group LLC, Mac’s Place LLC and Garbo’s Grill. Consultant Jon Shaw contributed $1,030.
Massicotte’s donor base included a mix of local residents, business owners and community supporters. His campaign has built a larger overall fundraising total during the election cycle, though his most recent reporting period was substantially smaller than Sullivan’s.
On the spending side, Sullivan reported $11,066.29 in expenditures during the reporting period and $11,097.95 in total expenditures to date. Massicotte reported $5,456.07 in expenditures during the quarter and $17,701.76 in total spending since entering the race.
The District II, IV and V contests are on the ballot in Key West’s 2026 municipal election cycle with the primary scheduled for Aug. 18.