Florida was admitted to the United States as a slave state in 1845. Florida had been a territory since 1821 and slavery was widespread, especially in the north, on cotton plantations and citrus farms around St. Augustine. One of the largest landowners was Stuart Dunleavy, a roguish politician who had once been a soldier and still fancied himself a military man. He would later get shot at Gettysburg and lose an arm. Using bribes and connections, he had amassed huge swaths of land east of Tallahassee and grew cotton on four thousand acres. When Florida joined the Union, he owned more slaves than anyone else in the new state and boasted of having a thousand Africans toiling in his fields.
Like most plantation owners, he was plagued by runaways and angered that many of his slaves were escaping to Dark Isle. Its legend continued to grow, and it was widely believed that hundreds if not thousands of slaves were hiding there, flouting the law.
In 1850, General Dunleavy, as he insisted on being called, decided to do something about it. He badly needed more labor and was fed up with the idea that the slaves were living on Florida soil as free men and women. He decided to capture them, keep all of them for himself, convert them to Christianity, put them to work in the fields, and in general improve their lives. He leaned on the governor, who, for some cash, agreed to “rent” General Dunleavy an old steamer that had been converted into a gunboat by the navy. He rounded up some troops, a motley mix of white farm laborers, common criminals, mercenaries, and a handful of real soldiers, gathered them on Camino Island, and spent a few days trying to train them, but finally gave up.
At dawn one morning they launched from the main harbor at Santa Rosa, with Dark Isle in sight. A quarter mile from shore they dropped anchor, positioned eight of the ship’s cannons, and began bombing away. Dunleavy’s brilliant battle plan was to bombard the island with the cannons, terrify the savages into surrendering, and send in his “troops” to capture them on the beaches.
The bombardment continued nonstop through the morning. By noon, there was no sign of the Africans, so the general and his men broke for lunch. After a meal and a nap, he gave orders to recommence the attack. At 3:00 p.m. his gunners reported that they were running out of cannonballs. Still, no sign of any terrified slaves waving white flags on the beaches. At 5:00 p.m. the cannons went quiet because there was no more ammunition. With an eye on the island, Dunleavy waited until dark, then retreated to their camp on Camino Island where they spent the night. The next morning, they reloaded and sailed to the southern end of Dark Isle where there had allegedly been signs of human activity in the past. They shelled the hell out of a thick forest, but saw no Africans.
After lunch, the general gave the dreaded orders. Two thirty-five-foot rowboats were lowered into the water and a dozen men boarded each. No one had volunteered for the little assault. Indeed, it was widely whispered on the gunship that there could be a mutiny if the troops were ordered to go ashore. The legend of Dark Isle and its cannibals was well known.
The men hit the beach and tied off their rowboats. One squad went north, one south. All of the men were armed with rifles and long knives, but they were moving far too slow and timidly in the general’s opinion. He watched intently with his field glasses atop the wheelhouse. Finally, they left the safety of the beach and disappeared into the dense woods. An hour passed, then another. Late in the afternoon, gunfire erupted at the southern end of the island, and this pleased the men on the boat. Part of the legend was that the slaves had only spears and darts and such, the weapons of their ancestors. How could they possibly have modern weapons? The gunfire meant they had been found and captured after a quick skirmish. Then there was more gunfire. It was comforting to hear but Dunleavy began to worry about casualties. He needed to capture the slaves, not slaughter them.
But the slaughter was on.
He had given his men strict orders to return to the gunboat by dark. However, as nightfall came there was no sign of the men on the beach. Their two rowboats had not moved. They had no food or supplies for the night. As the hours passed, a sense of fear and dread engulfed the gunboat. The general wasn’t sure what to do next. He couldn’t abandon his men on the ground and return to Santa Rosa. He gave orders to pass around whatever food could be found on the gunboat and stand guard. A long night was ahead of them.
At the first hint of dawn, the lookout began yelling. The men woke up and scurried to the deck. The two rowboats had been cast off the island and were drifting with the tide. At first glance, they seemed to be empty. Dunleavy ordered his captain to start the steam engines and move close to the rowboats.
