Black History Month

The Story of Jeffery Bolding, Sarasota's First Enslaved Man

A rediscovered photo sheds light—and darkness—on our history.

By John McCarthy Published in the February 2017 issue of Sarasota Magazine

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Jeffrey Bolding

In the 1980s, a small tintype of an elderly black man identified as Jeffery Bolding was discovered in the files of Sarasota County’s Historical Archives. The photograph, the oldest of an identifiable African-American in Sarasota County, reminds us that our own local history bears the stain of slavery and resonates with the complex and contradictory relationships between whites and Blacks that our nation still struggles to resolve.

After fleeing from the man who'd enslaved him in North Carolina, Jeffrey Bolding, a 23-year-old Black man, headed south to lose himself in the Everglades. After a month on the run, he was found, sick and exhausted, huddling in the palmetto scrub of Sarasota by pioneer William Whitaker.

While William’s wife, Mary Jane, nursed Bolding back to health, William negotiated to purchase him for $1,000. A few months later, Mary Jane purchased two individuals named Harriet and John at a Manatee River auction, while William purchased a young woman named Hannah. Hannah and Harriet worked in the house and helped care for the growing Whitaker family while the men tended to the gardens and groves and cleaned and salted fish. 

Hannah and Bolding soon fell in love. Their vows were witnessed by an African-American minister, and the wedding was attended by scores of folks from the Black community who were enslaved by the owners of Manatee sugar plantations.

There are unsubstantiated stories of Bolding’s tenure with the Whitaker family. When 12-year-old Furman Whitaker accidentally shot himself on a hunting expedition, Bolding found him and carried him home. Another story places Bolding in the wagon that smuggled Confederate Secretary of State Judah P. Benjamin from a hideout near the Manatee River to the Whitaker home as he eluded Union capture at the close of the Civil War.

Upon emancipation in 1863, the Boldings were taken to Key West by a Union detachment. While Hannah decided to stay in Key West, Bolding returned to live with the Whitakers and married a younger woman named Ellen. He died in 1904 at the age of 70, 47 years after arriving in Sarasota.

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