City dedicates Shady Park Pioneer Memorial

The busts honor Black residents central to the history of Winter Park and the Hannibal Square community

Aug. 3, 2024

By Charles Maxwell

Winter Park on Saturday dedicated the Shady Park Pioneer Memorial, which honors central Black figures in the city’s origin and development and underscores the significance of the Hannibal Square community. 

The memorial, which is next to Winter Park Community Center on New England Avenue, represents the endurance of Hannibal Square with four busts of key historical figures: Mary Lee Depugh (1878-1949), founder of the Ideal Woman’s Club;, Gustavus Christopher “Gus” Henderson (1862-1917), activist and founder of The Advocate and Frank R. Israel (1848-1925) and Walter B. Simpson (1859-1915) who both served as town aldermen. 

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The new Pioneer Memorial at Shady Park honors Black residents central to the city’s history. (Photo by Charles Maxwell)

Behind the busts is a pyramid with a small sculpture of elephant tusks, which signify Hannibal Square, said memorial artist George Gadson.

“The elephants represent symbols of strength, wisdom, and longevity,” Gadson said. “Their ability to overcome obstacles perfectly resembles these pioneers.” 

Today the black population in Winter Park has shrunk as the city’s west side has largely been redeveloped. But advocates say that makes the history lesson highlighted by the memorial even more relevant. 

“It’s crucial for everybody to know their history, where they come from,” said Maria Olivia Bryant, who grew up in the Winter Park and Eatonville area and has long pushed for the memorial. “It’s especially important for children to know and learn about their own culture, and that’s what the memorial is here for … If you know your history, it aligns you with your purpose.”

Founded in 1881, just 14 years after Florida reentered the Union after seceding and co-founding the Confederate States in 1861, Hannibal Square was home to free black families who provided labor and services to wealthy white residents. 

Across from the busts in Shady Park is a history wall with the stories of the pioneers and a timeline of the community’s history. The memorial is set at the former site of Hannibal Square Elementary School, which was the very first public school for African American children in the Winter Park area, founded in 1883.

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A crowd gathered Saturday at the memorial dedication at Shady Park.

Saturday’s dedication ceremony was crowded with local leaders and relatives of the pioneers. Mayor Sheila DeCiccio expressed her gratitude to community members who worked to make the memorial a reality. 

“This has been a long time coming,” said DeCiccio. 

Mary Daniels, a longtime resident and community leader who represented the MLK and Shady Park planning committee, gave remarks as well. 

During the ceremony, Bryant led a historic dramatization that told the stories of the pioneers. 

She noted how the idea for the memorial started more than 10 years ago, but it wasn’t until 2022 when a plan was really set into motion. 

“For the past 20-25 years, there were conversations, promises and denials … through working, and coming together, it was finally brought back up.”

Bryant credits the City Commission in 2022 with pushing the concept forward. 

When we brought it back up at that meeting, the commissioners and [former] Mayor [Phil] Anderson heard us,” Bryant said. “Actually, they didn’t just hear us. They felt us, they understood us.”

Anderson, who attended the ceremony Saturday, said he was just a part of the process that started before he was even in office. 

“We had the opportunity to allocate certain funds… about half a million dollars to Shady Park as well as the MLK Jr. Park memorial,” said Anderson. “The committee that ran with it has been working on this for a long time. I don’t know if I’ve seen a prouder moment in Winter Park.” 

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