Tampa entrepreneur, city leader, educator dies at 60

Gwendolyn Henderson, a Tampa City Council member, former educator and owner of the influential Black English Bookstore, has died. She was 60.

According to a statement issued by the city of Tampa Tuesday, she died of natural causes overnight at her home. She was taken by Tampa Fire Rescue to the hospital Tuesday morning but life-saving efforts were not successful.

“Councilwoman Henderson was a powerhouse in our community — she was a teacher, business owner and champion for African-American culture and Tampa’s history,” Jane Castor, the city’s mayor, and Alan Clendenin, council president, said in a joint statement.

“Her sense of humor energized our city and her loss leaves a deep void for us all.”

That was a sentiment shared by hundreds as word of her death spread Tuesday and social media was filled with comments — from community leaders, to colleagues to customers — about what it was like to work with her and her impact.

She was called a beloved teacher, a pillar and a trailblazer. St. Petersburg Mayor Ken Welch, on Facebook, described her “as a dedicated public servant, a passionate advocate and a cherished member of the Tampa Bay community.”

In an email to the Business Observer, Florida Aquarium President and CEO Roger Germann wrote that from her commitment to the community, to the bookstore, to being an advocate for the aquarium “Gwen’s legacy will be realized by generations to come.”

“Her commonsense approach, coupled with her compelling smile and laugh, is what made her one of a kind and why she was successful in business, public service and life,” he wrote.

“She will be missed.”

Henderson was a Tampa native who grew up to teach local children for 30 years before being elected as city councilperson in 2023 and opening a popular bookstore focused on Black voices later that year.

She was born in 1964 and raised in the Carver City neighborhood, a historically Black community between North Dale Mabry to the east and North Westshore Boulevard to the west and sandwiched between Boy Scout Boulevard and Cypress Street. This was long before nearby South Tampa began turning into the posh, nouveau riche enclave it is becoming today, and Westshore was a major commercial district.

The neighborhood, according to a historic marker erected by the city, came into being following World War II and in the lead up to the Korean War. This was a time when Black veterans weren’t allowed to take advantage of the housing provisions of the GI Bill. In 1948, the Veterans Administration, at the insistence of local veterans and families and the urging of MacDill Field Base Housing, developed the first planned Black subdivision, Lincoln Gardens, in the Carver City neighborhood.

Henderson, whose father was a Korean war veteran, was born into the community Oct. 5, 1964, and referred to herself on her Facebook page as a "Carver City Girl."

She attended Roland Park Elementary, Morgan Woods Elementary, West Tampa Junior High School and Pierce Junior High School, according to her official biography on the city’s website.

After graduating from Jefferson High School, she earned a bachelors in education from Florida A&M University and earned a masters in education and education specialist degree in educational leadership and higher education administration from Saint Leo University.

She worked for the Hillsborough County Public Schools for 30 years before retiring. That includes serving as secretary on the Entrepreneurship in Education Advisory Board.

“She was living her dream as a public servant and the proud owner of a local bookstore that reflected her love for community,” Casey Ellison, CEO of Ellison Development in the city and a fellow graduate of Jefferson High School, says in an email to the Business Observer. 

“Her fierce advocacy for education and equity made her a powerful voice in our city. We both believed in building a Tampa future generations will be proud of. Her leadership and spirit will be deeply missed.”

It was in her role as an educator, Henderson told the Business Observer last year, that the idea for the bookstore came to be.

It was 2022 and Henderson was teaching an entrepreneurship class when she decided to tackle the assignment of building a business alongside her students.

That business turned out to be the Black English Bookstore. It began online and eventually opened as a brick-and-mortar store in November 2023 at 401 East Oak Ave. in the Tampa Heights neighborhood where she’d lived for the past 30 years.

“Entrepreneurship is about opportunity and a need,” Henderson told the Business Observer. “Meeting a need or opportunity.”

The need was a bookstore that spoke to the community it was located in. According to its website, Black English is dedicated to elevating books by Black authors and brings a Black-owned bookstore to Tampa’s inner city.

The store’s name was inspired by James Baldwin’s 1979 essay, “If Black English Isn’t a Language, Tell Me, What is?”

“It's very intentional. I'm very intentional. And no one else has that,” Henderson told the Business Observer. 

But her work, especially after narrowly defeating Orlando Guedes 50.36% - 48.82% to represent District 5, was dedicated to more than just the store. She was fiercely dedicated to improving her community, those who knew and worked with her say.

(District 5 includes McKay Bay/Palmetto Beach, downtown Tampa, the Channel District and Ybor City.)

Christina Barker, president of Catalyst Communications Group and chief of staff for Jeff Vinik, says in an email that Henderson “was a champion for her district and each neighborhood she represented — never backing down from what she knew was right for her community.”

 “Her impact will be felt for generations to come.”

In addition to her work on the council and the bookstore, Henderson was the current chair of the Tampa Community Redevelopment Agency and a member of the Florida A&M University Alumni Association, Saint Leo University Alumni Association, American Booksellers Association, Southern Indie Booksellers Alliance and the Delta Sigma Theta Sorority.

According to her city biography, Henderson had a daughter, Ariel Amirah.