Tom DeGeorge at Crowbar in Ybor City, Florida on July 3, 2023. Credit: Photo by Dave Decker

Hot dog. Tampa’s special election for the vacant District 5 city council seat just got a little meatier.

Tonight at the 19th edition of his venue’s infamous Hot Dog Party, Crowbar owner Tom DeGeorge told partygoers he was throwing his hat into the race for a seat left vacant after the passing of first term councilwoman and Tampa native Gwen Henderson.

“I am entering this race to be a fighter and a voice for the people that make up the heart and soul of District 5,” DeGeorge told Creative Loafing Tampa Bay in a text message ahead of tonight’s announcement. “Too often, the boots on the ground doing the work in our communities have been left marginalized and unheard. I have lived my Tampa dream doing what I love for close to 25 years—I’m going to make sure everyone here can have their dream too. I want to be a force for change.”

The special election ends on Sept. 9, with early voting running Sept. 4-7. The deadline to register to vote is Aug. 11. Anyone who wants to vote by mail must ask the Hillsborough Supervisor of Elections for a mail ballot.

If no candidate receives more than 50% of the vote, a runoff election will be held Oct. 28.

Only registered voters who live in Tampa’s District 5—which stretches west-to-east from Tampa to parts of the end of Broadway Avenue and north-south between parts of Riverhills to Harbour Island—can vote in the election.

District 5 currently includes just under 44,000 active registered voters, according to the supervisor of elections. In the 2023 election, the District 5 race saw Henderson defeat embattled incumbent Orlando Gudes by just 81 votes.

DeGeorge, who live a short walk from Crowbar, has never held elected office before but is no stranger to getting things done. In the wake of the pandemic, he found himself helping lead the then-nascent National Independent Venue Association as it successfully lobbied congress for the $15 billion “Save Our Stages Act” that helped save the country’s live music industry.

He worked in conjunction with 40 indie venue owners to get the legislation over the finish line, and saw his face on the pages of the New York Times, Billboard, Rolling Stone and other publications as part of the effort.

DeGeorge is not alone in the race for the District 5 seat either.

Ten others have filed applications to run for the seat including Ariel Amirah Danley, daughter of the late Councilwoman Henderson, the aforementioned Gudes who held the seat before Henderson, Bishop Thomas Scott (a former Hillsborough County Commissioner) and fellow Ybor City business owner Ash Dudney.

Gudes has already earned the endorsement of State Rep. Dianne Hart, but won’t necessarily have an easy path to getting his old job back. He was elected in 2019, but only served one term after claims that he created a toxic workplace through caustic, inappropriate, language and behavior resurfaced during a particularly fractious time between Tampa Mayor Jane Castor’s office and city council. He denied those allegations, but it was the late Gwen Henderson’s sister—who was Gudes’ aide—who was at the center of that controversy.

The sexual harassment lawsuit against Gudes, who served 26 years with Tampa Police Department, was dismissed after the City of Tampa agreed to a settlement with Henderson’s sister. The city also paid Gudes $45,000 to cover his legal fees.

The rest of the applications came from Audette Bruce (a pastor at Revive Church), Realtor Juawana Colbert (of “Selling Tampa” fame), perennial candidate Elvis Piggott, President of the Jackson Heights Neighborhood Association Fran Tate, military veteran Melony Letitia Williams, and Director of the Tampa Heights Junior Civic Association Naya Almaz Young.

The special city council election in the City of Tampa’s District 5 is happening because there are more than 15 months left on the late Gwen Henderson’s term as city councilwoman.

Tampa City Charter (Section 10.01. – Miscellaneous—Elections and Vacancies, Section 4) says that the Supervisor of Election will run a special election. Technically, candidates must be given at least five business days to qualify for the special election.

“…but there shall be a period of at least thirty (30) days in which to allow candidates to circulate qualifying petitions. The special election shall be held on the forth [sic] Tuesday following the date of the deadline for qualifying,” the charter adds.

Just over a year ago, Tampa City Council members voted to give themselves a raise from roughly $54,000 to $75,000. At the time, Henderson pointed out that the bump would give an average person the opportunity to service their city without getting a second or third job. “If you looked at it from if this was a full-time job, can a person afford to live in the city that they’re actually governing,” she added during a workshop on June 27, 2024.

To officially qualify for the special election ballot, according to the city charter, applicants must pay a qualifying fee equal to 5% of the salary (roughly $3,750). A fact sheet from the Hillsborough County Supervisor of Elections points out that the qualifying fee would be $4,511.52 because an additional 1% election assessment is required by the State of Florida.

Another way to qualify is to submit petition signatures from 0.25% of the population of the city of Tampa by Aug. 1.

Full disclosure: DeGeorge served as this reporter’s boss for a short time between 2004-2005 when he worked as a security guard at DeGeorge’s Masquerade nightclub in Ybor City.

UPDATES
(07/07/25 4:19 a.m. EDT) with more information on the election and other candidates in the special election for Tampa City Council District 5.
(07/09/25 4:56 p.m. Corrected to show that 5% of the $75,000 salary is $3,750, not $375)
(07/11/25 3 p.m. Corrected because the 1% signature qualification is for mayoral races.)

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