Community Sunday Favorites: The Last Slave of Sarasota

The Whittaker Home was located on Yellow Bluff in Sarasota

SARASOTA – It’s hard to imagine a time when people were under the ownership of others, and even harder to conceive that a slave and an owner could build a friendship so strong, their bond withstood the duration of the Civil War. However, William Whittaker and Jeffery Bolding were bonded by blood -- William saved the life of Jeffery, and Jeffery saved the life of William's son. 

William Henry Whittaker, considered the founder of Sarasota, was riding out on the cattle range one day when he heard a peculiar noise in a thicket of saw palmettos. Upon further inspection, he discovered a frightened young boy whose scrawny frame exhibited his dire situation; he was starving and ill. 

Whittaker hoisted the boy upon his horse and rode with him back to his home at Yellow Bluff, just north of present day Eleventh Street, and left the boy in the care of his wife, Mary Jane Wyatt Whittaker. As she nursed him back to help, the boy divulged more of his story. His name was Jeffery Bolding. He was an escaped slave that had run away from his abusive owner in North Carolina. 

The story struck a sympathetic sentiment in William. At age 12, he too had run away when he became unhappy from the treatment of his stepmother. From Savannah Ga., he had traveled to Charleston S.C. and acquired a position aboard a cargo vessel. He eventually made his way to Tallahassee where his older stepbrother, Hamlin Snell, attended school. The two worked as crewmen aboard fishing boats until they saved enough money to purchase their linked properties at Yellow Bluff. While Hamlin became engrossed in politics, William expanded his fishing commerce to include cattle trade and citrus farming. 

Jeffery Bolding saved the life of Furman Whittaker, who went on to become Manatee County's first native-born doctor.

William contacted Jeffery’s owner in Charleston and negotiated the acquisition of the young man. He paid a total of $1000 for him; Jeffery  was the first slave William had ever purchased and the first recorded slave in Sarasota. William liked doing things himself, but knew he needed a helping hand around his ranch. The family had first lived in a palm frond shelter, then Hamlin and Jeffery had built a log cabin, and now a handsome house stood on the property. Seminoles had burned the log cabin during the Billy Bowlegs War, and their helping hand, an Irishman named Owen Cunningham, was murdered.

Luckily, the rest of the family was safely secured at Fort Branch, a fortified encampment near Manatee Mineral Spring. It was there that Mary Jane gave birth to the first baby born in Manatee County – Furman Whittaker. 

Jeffery was such a help to William, that when a slave auction happened in Sarasota in 1857, three more slaves were purchased – Hannah, Harriet and John. Hannah and Jeffery fell in love and were married in a black church in Manatee. For years, they lived together on the Whittaker estate. Jeffery worked outside while Hannah helped care for the children and keep the house clean. 

Near the end of the Civil War, Jeffery aided with the escape of Confederate Secretary of State Judah P. Benjamin. Judah had been in hiding at the Gamble Plantation while a select few men tried to figure a way to get him out of the country. Captain Archibald McNeill recommended two ”good men to carry him out.“ Judah was transferred to the south side of the Manatee River to Capt. Fred Tresca’s home in the Village of Manatee, where he was known as ”Mr. Howard.“ 

Ezekiel Glazier and Jeffery Bolding drove a two-wheel spring wagon to Sarasota. In the wagon was Judah, hidden under a load of freshly butchered beef covered with palmetto fans. From there the wanted man was transferred to a boat and secretly deported. 

The end of the Civil War brought along change, and all the slaves were now freed. Jeffery and Hannah took the opportunity to visit the West Indies; Hannah wanted to stay, but Jeffery was dedicated to the Whittaker’s. He came back without her and continued work on the Whittaker farm. Jeffery had gone from becoming the first slave to the last formal slave in the area. He took a new wife named Ellen shortly after.

One night, Furman didn’t arrive in time for supper. Jeffery became extremely worried and went out to look for him. He knew where Furman had gone because he knew the boy’s habits. He found the boy nearly a mile from the house barely able to move. He picked him up and carried him all the way home – saving his life.

Furman had been out hunting for wild turkey and deer. He was only 11, so when he couldn’t see over the thicket, he climbed upon a fallen down tree. While hoisting himself up, he rested the butt of the gun on the tree and cradled the barrel in the crook of his arm, but the butt slipped and the rifle fired, shooting him in the elbow. He made a tourniquet out of his shirt and began home along the coast, stopping frequently to wash the wound with salt water. The loss of blood made him weak, and he was about to give up and collapsed when Jeffery found him. The man hoisted the boy over his shoulder and carried him the rest of the way. 

Furman never completely recovered from the injury; and could never fully extend his arm. Because he would never be able to perform physical labor,  he was sent to Danville, Kentucky to study medicine, eventually becoming the first Eye, Ear and Nose specialist to practice in Manatee County. 

Jeffery and Ellen remained with the Whittaker’s until William’s death in 1888. Mary Jane moved to Tampa, and Jeffery and Ellen were taken into the home of William Richard. They remained there until Jeffery’s death in 1904. Dozens of loved ones, both black and white, attended the funeral.  

The Whittaker’s loved Jeffery so much, that he is included as part of their family history.