Tampa’s new Black City Council member bucked political tradition and won

Educator Gwen Henderson’s sister accused incumbent Orlando Gudes of creating a hostile workplace, but Henderson says that’s not why she got in the race.
Longtime educator Gwen Henderson attends one of her first meetings as a member of the Tampa City Council. That big ring on her finger? A football championship ring from Jefferson High.
Longtime educator Gwen Henderson attends one of her first meetings as a member of the Tampa City Council. That big ring on her finger? A football championship ring from Jefferson High. [ LUIS SANTANA | Times ]
Published May 15|Updated May 16

For the ceremony in which she was sworn in as a new Tampa City Council member, educator and political newcomer Gwen Henderson asked her younger sister to hold the Bible.

Favorite relatives often get picked for this. But given her sister’s connection to an explosive scandal that rocked City Hall, it was a particularly notable request.

As an aide to council member Orlando Gudes, Henderson’s sister was at the center of allegations that Gudes made a litany of crude, inappropriate and sexual comments — which Gudes denied or said he did not recall.

Gudes was the very incumbent Henderson had just defeated on Election Day.

But Henderson — who ran despite people saying she should wait her turn, should run elsewhere or should respect a hierarchy in Tampa’s Black community — said Gudes was not the reason she ran.

“There are people that had silent rules: You shouldn’t run against him,” said Henderson, 58. “I gave Black people a choice in this community.”

She grew up on the west side of town in Carver City, where as teenagers she and her sister got jobs with the city. One of her sister’s assignments was to count the cracks on the Bayshore Boulevard sidewalks in monied South Tampa. Their own neighborhood didn’t have sidewalks, much less the funds to fix them.

“My community had to fight for stuff like that,” she said.

Henderson was a single working mom raising a toddler in 1993 when Vice President Al Gore came to her Tampa Heights home, photographers in tow.

Through a city program to help low- and middle-income buyers get low-interest home loans, Henderson bought a house once trashed by vagrants and transformed it into a pink and white home with an airy porch, fireplace and new kitchen. She told Gore that without the program, it likely would not have been possible.

Vice president Al Gore at Gwen Henderson's Tampa Heights home in 1993.  Her daughter Ariel, 3, made the vice president laugh when she was asked to name his boss and replied "Hillary.”
Vice president Al Gore at Gwen Henderson's Tampa Heights home in 1993. Her daughter Ariel, 3, made the vice president laugh when she was asked to name his boss and replied "Hillary.” [ Associated Press (1993) ]

As the department head of career and technical education at her alma mater, Jefferson High, Henderson has the ease of someone who’s spent years collaborating with children and adults alike. A political veteran advised her not to talk to everyone like they’re a friend. It does not seem to have taken.

The possibility of politics was sparked by a bad experience with code enforcement when she was trying to get a new roof during the pandemic, and also a book she read called “Run for Something: A Real-Talk Guide To Fixing the System.″ Don’t just march, it told her. Run.

“I think the fact that I’m not super political is a benefit to me,” she said. “I don’t owe anybody anything.”

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Advisers steered her toward the citywide race against incumbent Lynn Hurtak, who had been appointed and never had competition. Henderson was in. Then, former state legislator Janet Cruz — a big Tampa name and mother to Mayor Jane Castor’s domestic partner — jumped in against Hurtak in what would become the most contentious City Council battle.

Meanwhile, the challenger to Gudes for his seat representing East Tampa, Ybor City, downtown and part of West Tampa — the only district with a majority of minority residents — dropped out.

A retired police officer, Gudes was elected in 2019 and spent most of his term under fire after his aide reported offensive comments. Allegations included statements about her looks and her teenage daughter’s breast size and crude and homophobic comments about the mayor. Gudes denied many of the allegations but admitted to comments “not appropriate for the workplace.”

The mayor said she would fire him if she could. He refused suggestions that he resign.

Former Tampa City Council member Orlando Gudes
Former Tampa City Council member Orlando Gudes [ ARIELLE BADER | Special to the Times ]

The city reached a $200,000 settlement with the aide after a finding that she had been subjected to a hostile workplace. She now works in another department.

While some denounced Gudes, others stayed in his corner. At a meeting, one called it a page from “the age-old book of how to get rid of a Black man.” Yvette Lewis, president of the Hillsborough chapter of the NAACP, said some saw it as an African American targeted by city staff.

Gudes declined to comment. The aide, who is not named because of the nature of the allegations, also declined.

Henderson had a decision to make. Running citywide was expensive and Cruz was in the mix, and she did not want to see Gudes unopposed.

“I have a right to run where I want,” she said. “I could see it: District 5 was the pathway to victory.” Two days before the deadline, she switched ― after making sure her sister was OK with it.

“When I signed the papers, I had no problem,” she said.

Gwen Henderson campaigns in Tampa.
Gwen Henderson campaigns in Tampa. [ DIRK SHADD | Times ]

The seat is an important one — “the closest thing we’ve ever had to a Black mayor,” said Fred Hearns, curator of Black history at the Tampa Bay History Center. “The closest we’ve come to having a Black person with that kind of power in the city is that seat.”

It’s “quote unquote, ‘that one Black or African American seat,’” said the Rev. Tom Scott, a former council member and Hillsborough County commissioner.

Gudes “did some good stuff for the district,” Scott said. “Unfortunately, the negative outweighed the good that he did.”

Henderson said it was clear on the campaign trail that part of the community didn’t believe Gudes did anything wrong. Some thought she got into the race at the behest of the mayor.

“And I’m like, I don’t know that lady,” she said.

When a negative Gudes ad surfaced, she said, some thought it was her doing.

“I said, ‘You think I could afford to do that?’” she said. “I wouldn’t have even thought to do that.”

But she found support, too. “Then there were people that said, ‘Oh, I like that girl,’” she said. Hearns said he thought she deserved the chance to lead.

“There are people who got behind her because we wanted somebody who could represent the district and not have a stigma,” said Scott. She won by 80 votes.

But victory did not immediately end the pushback. An online commenter said her heart was heavy with Henderson’s election. Another used the word “dog.”

“You sure as hell did not win with the respect of so many of us in East Tampa,” said an email to all council members accusing Henderson of having “disrespected” and “slandered” Gudes.

Henderson said that as an educator, she’s had to “coach girls to ignore the noise.” She said she also understands some people are mourning a loss.

“Knowing Gwen, she does not hold grudges,” said Hearns. “I can’t say she doesn’t hear it, but it’s not going to affect her adversely sitting on City Council.”

Lewis said right now, there’s a divide. “But I look to the councilwoman to be the stronger person, the better person‚ to stand up to mend the hearts and go out and seek the ones who didn’t support her and show them that she is capable and qualified,” she said.

“A major divide,” said former state legislator and County Commissioner Les Miller, who supported Gudes and calls him a friend. “There’s some bitterness,” particularly from those who feel bad for Gudes and are aware of who Henderson’s sister is.

But in a district in need of development, jobs and affordable housing, “it’s time for all of us to rally around her to make sure she’s successful,” he said.

“I sat on the board where there’s only one Black person there,” said Miller. “If you don’t have that support behind you, you’re in trouble.”

During her first regular City Council meeting came the resolution of a painful issue in the Black community: a city plan to purchase Memorial Park Cemetery after it had been bought by a property flipper. Henderson thanked the staff and “every single citizen that cares about Black bodies in the ground.”

For that swearing-in, she told her sister: “You’re going to walk in that door and square your shoulders and tell the world you survived,” she said. When the oath was over, she lifted her sister’s chin and they hugged.

“The cheering, I thought that would help her out a lot,” Henderson said. “We won.”