More than three dozen people braved the Florida-cold last Friday to watch Alan Henderson open the gate in the race to be Tampa’s next mayor.

The night before his announcement, the Brandon High School alum, who turns 24 years old on Feb. 6, told Creative Loafing Tampa Bay that he wants his campaign to be optimistic, focused on collaboration and focused on the future of the city. If elected, he would be Tampa’s first Black mayor—but he would not be its youngest (that title belongs to James Edgar Lipscomb, the 13th Mayor Of Tampa, who served from 1873-1876, who was 23 years old when he was sworn in).

Tampa’s current mayor, Jane Castor, won re-election in 2023 and is term-limited; voters won’t decide on her replacement until 2027.
[content-1] During the press conference, friends and supporters took to a podium and described Henderson’s kindness and character. His older brother Roderick, ten years his senior, described how a four-year-old Henderson used to sit in restaurants and have full-blown conversations with adults.

“He just was different,” Roderick said, telling a story about how as a child, Henderson started a photography business. “When most kids were out playing sports, he was out taking pictures of the kids that was playing sports and selling the pictures to the parents. I was like, ‘Dang, this boy got a lot of business sense inside of him.’”

Henderson—a self-described entrepreneur who votes in Hillsborough Precinct 859, according to records at the Supervisor of Elections—recently led an esports company that landed him on a Tampa Bay Business Journal list of young residents to watch. He told supporters that in Tampa that someone’s dreams can be as real as the hard work they’re putting in. He also applauded the city’s resilience after back-to-back hurricanes. He, too, had to find strength after the recent loss of his mother, who supporters said would be proud of him.

“We’ve proven time and time again—we don’t just bounce back, we bounce back stronger,” Henderson added. “Tampa has always been a community that faces challenges head on and refuses to back down. It’s a city where resilience isn’t just a trait, it’s our way of life—and that’s why I’m so proud to call this city my home.”

Online, his campaign touts a vision centered around empowering communities, sustainability, and “building the Tampa of tomorrow today.”

While he’s shared thoughts on modular housing, Tampa’s dissolved police citizens review board and how he voted on state amendments, Henderson offered a few more specifics about his views during the announcement speech. Beyond “heartbreaking,” he said that seeing people have to sleep under bus shelters for warmth is “unacceptable.”

“Tampa doesn’t just end on Ashley Drive or Water Street. We have obligations to constituents all across the city, from West Tampa to East Tampa, from the Channel district to New Tampa,” he said. “Every neighborhood, every individual, every family, every person, deserves to feel seen, valued and supported by their city’s government.”

He pointed to public policy and leadership classes he’s taking at the Harvard Kennedy School, and his experience “scaling multi-million dollar teams” for local clients, as part of his preparation for the roles.

The Monday after his announcement, Henderson told CL that he’s launched a “Tomorrow Team” where “experts, scholars, citywide leaders and passionate volunteers” from around the country will work together to address key issues facing Tampa. He did not share the names of individuals in his coalition, but said he’d make introductions in the coming weeks.

“I’ve designed these teams to help analyze the city’s challenges, host public forums, and provide actionable insights on matters that align with my campaign promises,” he said. “Our plan is to leverage their findings to inform solutions and share them with the public in a clear and accessible way, ensuring transparency and community involvement throughout the process.”

But as a more-or-less political unknown, Henderson has his work cut out for him. While the race for Tampa’s mayor is nonpartisan, Henderson is a registered Democrat who will undoubtedly need support from his party.

“The party is the one that’s going to go canvas for you. They’re the ones that help you raise funds, they’re the ones that open the right doors or talk to the right people,” Luis Salazar, President of Hillsborough County LGBTQ+ Democratic Caucus, told CL.

Salazar added that in an eventual primary, Henderson could end up running against big name Democrats. Councilmen Luis Viera and Bill Carlson, plus former Mayor Bob Buckhorn have all been floated as potential candidates. One of those men has even reached out to Henderson since his announcement.

“Viera, who wished me good luck,” Henderson said.

Republicans, Salazar explained, will be in the field, too.

“The GOP is feeling very emboldened right now because of the huge wins they had across the state and across the country,” Salazar said, adding that his caucus’ support helped push some candidates over the edge in the last municipal election.

Henderson said he’s planning to attend as many upcoming events to connect with local leaders and open up collaborations. He’ll have plenty of opportunities. This week includes a meeting of Salazar’s LGBTQ+ Caucus and the North Tampa Democrats. Hillsborough’s Democratic Black Caucus meets on Jan. 9, with the rest of the month seeing Democrats from East Hillsborough, South Tampa, and Temple Terrace meeting over the next two weeks. The nonpartisan Tampa Tiger Bay Club even hosts a post-election discussion with Hillsborough party leaders on Feb. 21.

Salazar said he can’t fully support Henderson yet, simply because he still doesn’t know who he is, but added that he’s ready to have a conversation and start building the trust that helps candidates win voters. Overall, however, he strikes an optimistic tone around Henderson’s campaign launch.

“It’s smart of him to start early. It is the new playbook, and he’s doing what he’s got to do,” Salazar said, pointing to Trump whose rewriting of campaign norms exposed the need to run year-round.

Young blood and new perspectives might be what the party needs, too. Especially in a county where there are only 2,232 more registered Democrats than Republicans.

“These last elections also told us that just because things seem secure—Hillsborough County seems like a pretty secure blue Democratic area—they are not,” Salazar said. “We really have to be putting ourselves out there to be ready for that.”

UPDATED 02/19/25 8:49 a.m. Corrected to note that James Edgar Lipscomb was Tampa’s youngest mayor.

Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Alan Henderson at Joe Chillura Courthouse Square in Tampa, Florida on Jan. 3, 2025. Credit: Photo by Dave Decker
Alan Henderson at Joe Chillura Courthouse Square in Tampa, Florida on Jan. 3, 2025. Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker
Credit: Photo by Dave Decker

Read his 2016 intro letter and disclosures from 2022 and 2021. Ray Roa started freelancing for Creative Loafing Tampa in January 2011 and was hired as music editor in August 2016. He became Editor-In-Chief...