Key West’s Civil War: Back in September 2012, sitting on an Outer Banks back deck, my baby brother and I mapped out a path to a Second Civil War. It was a desultory, leisurely conversation, filled with imagination and philosophy. How could it possibly be otherwise?
Those were long years before today’s divisive and unresolved frustrations exploded into public headlines. Joe Biden was Barack Obama’s vice president. Donald Trump was firing folks on “The Apprentice” and telling students at Jerry Falwell’s Liberty University that it was time to make America number one again. “Make America Great Again” wasn’t a thing. The only people who could imagine a global pandemic were scientists writing scholarly papers the rest of us rarely read.
Robert and I share similar core values but our political solutions diverge frequently. Yet that afternoon under North Carolina’s blazing sun and blue skies, we were in sync. There was a path for a Second Civil War, and it wouldn’t look anything like the first one.
For example, the first one violently pitted physical locations — North and South — against each other. A second would, we said, be more like the Revolutionary War, in which battles were fought — ideologically and physically — in scattered locations, right down to neighborhoods. So unless we actually see a repeat of secession and the creation of a confederacy, it’s hard to imagine a “War Between the States” of the 1861-1864 variety.
In fact, I said a dozen years ago, a Second Civil War could look like Key West’s first one. Despite its extraordinarily diverse demographics, Key West was a Southern slave-owning town by the 1860s. Its wealthy, educated white citizens, a list of which reads like a who’s who of current street names, were proudly secessionist. They owned slaves to take care of their homes and children and to rent out, particularly to the U.S. Army to build Fort Zachary Taylor. Rebel banners flew everywhere across the island, and its political leaders were delighted on Dec. 12, 1860, to nominate delegates to Florida’s upcoming secession convention on Jan. 3, 1861.
Key West’s Civil War | Ready for secession
Key West was ready for secession. Its outspoken white residents were joyfully on board with preserving their Southern slave-owning culture. Change was not a good thing, nor was having the Northern government tell them what to do. The island’s Southern leanings, combined with its libertarian underpinnings, had its residents spoiling for a fight.
But the night before delegates were chosen, something had happened that would change everything. On Dec. 11, Capt. James M. Brannon asked for permission to secure Fort Taylor for the Union should Florida vote to secede. It did, and on Jan. 26, 1861, he moved his troops from the barracks on White Street, took command of the fort and kept it — and Key West — in Union hands for the remainder of the war.
Brannon expected the city’s secessionists to attack the fort, a not unreasonable assumption given that he would have been aware of what was happening in Charleston, S.C., at the time. South Carolina, which had already seceded, was deep into gleeful preparations to take Fort Sumter from the United States. It did so on April 12, 1861.
Key West didn’t even shrug. There seemed to be a collective understanding of the futility of 3,000 residents, including 451 slaves, taking up arms against well-provisioned U.S. Army troops inside a fortress surrounded by water. By April 6, 1861, when the Fifth United States Artillery arrived to reinforce Fort Taylor, Key West did what it always does.
The get-along-to-go-along crowd changed flags, the hardcore secessionists slipped out of town to join the Confederate forces, the pro-Union folks who’d heretofore kept their heads down ratted out their rebel neighbors and everyone went to work seeing how much money they could squeeze out of the mess. A lot it turned out because the Union forces needed labor, so Key Westers bought more slaves and rented them to the fort. And, they provisioned the fort and resold booty from captured ships. Key West knows how to turn a profit.
On Jan. 18, 1863, word arrived in Key West that President Lincoln had on Jan. 1, signed the Emancipation Proclamation. When news of the proclamation arrived, one resentful islander wrote, “The colored ‘gemmen’ of Key West and elsewhere must not suppose that because they are free, we, the whites, are slaves, for if they try that on, as I think they will, woe betide them.”
On Jan. 26, Sandy Cornish, the island’s most successful farmer and leader of the Black community, led 250 men plus their families and friends in celebration through the streets of Key West, ending at the Baptist church. Though determined confederates threw rocks and water along the parade route, the celebration that evening, including the military and local sympathizers, went well into the night.
The U.S. Army soon thereafter conscripted the former slaves and used them as unpaid labor at Fort Taylor and Fort Jefferson.
Upwards of three-quarters of a million soldiers and others died in four years the Civil War raged on the mainland. In Key West, thousands of miles from the epicenters of Gettysburg, Richmond, Charleston and Atlanta, we went about our business, arguing with neighbors, raising dueling flags, writing nasty letters to the editor, remaining unfailingly focused on making a buck while living and letting live.
Will there be a Second Civil War? Perhaps. If there is, I suspect there’d be no better place than Key West to weather that storm. Although a friend suggests we might have to blow up the Cow Key Bridge.
Learn More
https://fcit.usf.edu/florida/docs/k/keys15.htm





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