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In 1886, after he was fired from his sales job when his white colleagues complained to his employer that he was black, Henderson moved to Hannibal Square, an African-American community on the west side of Winter Park. There the 24-year-old started a general printing and publishing company, according to records from the Winter Park Public Library and Rollins College.
A year later, two men from the Winter Park Company, Loring Chase and Oliver Chapman, wanted to incorporate Winter Park as a city. The white community in the area was opposed to allowing the black Republican population of Hannibal Square to become part of their community, but Henderson was not going to allow his community to be shut out. According to documents at the Hannibal Square Heritage Center, he successfully rallied African-Americans to march across the railroad dividing the two communities and vote to include Hannibal Square in Winter Park. The community also elected Walter B. Simpson and Frank R. Israel as the first two black representatives of Winter Park's city government.
Knee-deep in local politics, Henderson decided to found the Winter Park Advocate in 1889, one of only two black-owned newspapers in Florida at the time. His publication was unique in that it was popular among black and white residents alike. He printed stories on the opening of the first school for black children in Hannibal Square, local elections and the nearby all-black town of Eatonville. (Eatonville had its own newspaper, the Eatonville Speaker, which listed a "G.C. Henderson" as its business manager and called for black people to solve the "race problem" by moving to the town, says Scot French, director of public history at the University of Central Florida.)
Julian Chambliss, chair of Rollins College's history department, says it was common in Southern cities to suppress the black vote through legal methods, such as the poll tax, literacy tests and redistricting, to more violent methods, like lynchings and mob violence. But in smaller towns like Winter Park, black and white residents could interact in a less intense environment, which is why Henderson's paper was so successful – he could operate a newspaper for the entire community and still ensure that African-Americans had a voice in town.
"Henderson is active in a period where white Democrats are trying to push people out of the public sphere," Chambliss says. "And he says, 'No, I don't want to be pushed out.'"