Janelle Irwin Taylor
Tampa City Council candidate Orlando Gudes does not appear to meet residency requirements for the District 5 Special Election, according to a voter audit report from the Hillsborough County Supervisor of Elections obtained by Florida Politics.
The report shows Gudes submitted an address change on June 17, 2025, putting him in District 5. Prior to that, Gudes was registered to vote in Tampa City Council District 7, north of the district he’s seeking, since July 21, 2023.
The Tampa city charter requires candidates to “have been residents of the respective districts from which elected for six months immediately preceding the commencement of the term of office.”
Hillsborough County Supervisor of Elections Craig Latimer scheduled a Special Election to replace the late Gwendolyn Henderson, who passed away suddenly last month, for Sept. 9. If no candidate receives more than 50% of the vote, a runoff election will be held Oct. 28.
Whomever is elected would take office immediately upon election results being certified. Neither the September nor October election dates would put Gudes in District 5 for the required six months.
Gudes was not immediately available for response. He changed his address the same day as Henderson’s memorial service.
Gudes is one of 11 candidates filed so far for the Special Election. Elected in 2019, Gudes previously served one term on City Council, but scandal plagued his service. That included claims, which Gudes denies, of creating a hostile workplace and making inappropriate comments. The allegations led to Gudes’ defeat against Henderson in 2023.
Henderson’s sister was at the center of the controversy plaguing Gudes’ tenure. She was an aide to Gudes and made several claims against her boss, alleging inappropriate comments, sometimes sexual.
The allegations prompted a city investigation, which found 18 of the claims in a lawsuit to be credible. Gudes never resigned, and the sexual harassment lawsuit against him was eventually dismissed after the city agreed to a settlement with the victim. Eventually though, the city agreed to pay Gudes $45,000 to cover his legal fees accrued while defending the civil suit.
In addition to criticism over the scandal when Gudes served on the City Council, he also faces potential pushback over his disciplinary record from his 26-year service with the Tampa Police Department. That includes an incident in which Gudes left his service weapon unattended in his vehicle, resulting in a teen he was to give a ride home to that evening accidentally shooting his sister in the leg.
Later, Gudes was suspended over allegations that he lied about details of an arrest. Other disciplinary records outline situations when Gudes made inappropriate comments or other careless oversights while on the job that compromised investigations.
Other candidates in the District 5 race include Henderson’s daughter, Ariel Amirah Danley; Thomas Scott, a former Hillsborough County Commissioner; Realtor and reality TV star Juawana Colbert; photographer Darrell Ashley Dudney; owner of the popular Crowbar, Thomas DeGeorge; Fran Tate, who works in medical coding for Moffitt Cancer Center; Melony Letitia Williams, a Republican who previously ran unsuccessfully for Hillsborough Clerk of Court; Audette Bruce, a former district aide for Republican Rep. Berny Jacques; community advocate Naya Young; and perennial candidate Elvis Piggot.
There’s still time for even more candidates to join the already crowded race. Candidate qualifying begins Aug. 11 and ends Aug. 15. Early voting for the Special Election will run Sept. 4-7 from 10 a.m. until 6 p.m., with polls open on Election Day from 7 a.m. until 7 p.m.
Given the large field, it’s almost certain a runoff in October will be required.
Because Henderson passed away more than 15 months before her term would have ended, a Special Election is required to fill the remainder of her term.
