Orlando Gudes wants his old job back.
Gudes is joining an increasingly crowded field to run in the Special Election for Tampa City Council District 5, bringing the number of candidates in the race to replace the late Gwendolyn Henderson to nine as of Tuesday.
Elected in 2019, Gudes served just one term after 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.
His entrance into the race sets up an interesting few months as candidates jockey for the job on a truncated Special Election timeline. Gudes joins his predecessor’s daughter, Ariel Amirah Danley, as well as Realtor Juawana Colbert, perennial candidate Elvis Piggot, former Hillsborough County Commissioner Thomas Scott, Fran Tate, Melony Letitia Williams, Naya Almaz Young and Darrell Ashley Dudney.
It was Henderson’s sister who 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.
While critics are likely to use the allegations against Gudes on the campaign trail, it’s likely he’ll point to the city’s agreement to pay his legal fees and the dismissal of the suit against him as evidence of his innocence. It’s also likely he’ll accuse critics of playing politics — Gudes was, at the time of the allegations in 2022, part of a three-member coalition of City Council members at odds with Mayor Jane Castor.
But that’s not the only critique Gudes is likely to face. His disciplinary record from his 26-year service with the Tampa Police Department — a portion of which he served under Castor when she was Chief of Police — included 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, he 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.
Hillsborough County Supervisor of Elections Craig Latimer scheduled a Special Election to replace Henderson for Sept. 9. If no candidate receives more than 50% of the vote, a runoff election will be held Oct. 28.
Candidate qualifying for the race begins Aug. 11 and ends Aug. 15. The deadline to register to vote for the Special Election is Aug. 11.
To run, candidates must have been a resident in District 5 for at least six months prior to the date they assume office and a resident of the city for one year.
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.
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.
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