The tension on the Emerald Coast in the summer of 1861 was palpable, fueled by a mixture of deep-seated local loyalties, a new and looming conflict, and a single man caught in the middle: Captain Leonard Destin.
For the residents of the East Pass, the arrival of the Union vessel USS Water Witch in July 1861 to patrol the waters of the Gulf set off a chain of events that would see a local fisherman turned into a political pawn.
Leonard Destin, a Connecticut-born fisherman who had settled on the East Pass a decade earlier, found himself under immediate suspicion. As a Yankee in a land newly hostile to the Federal government, he had eyes affixed to him. On July 6, 1861, when the USS Water Witch visited his home, it moved his fishing boat and seized his property.
Determined to recover his livelihood, Destin rowed out to the Water Witch to negotiate with the Union sailors. He didn’t know it, but his diplomatic errand had been observed. Journals from local militia members of the Walton Guards, who were in the area reconnoitering the vessel, mentioned his interaction with the Union vessel. The interaction was interpreted through the lens of wartime paranoia: Destin could have colluded with the enemy.
After Destin petitioned the sailors to release his boat and property, the situation escalated. On July 12, at 4:50 a.m., as Union sailors attempted to make shore, they were met with a volley of rifle fire from the Walton Guards. The sailors retreated, and by 6:30 a.m., the Water Witch returned fire with its cannons. While the exchange was brief and resulted in no casualties, though the rebels claims would say otherwise, it marked a definitive end to the relative peace of the area.
The departure of the Water Witch on July 15 did not quell the suspicions against Destin. On August 20, the Walton Guards, acting under orders from General Braxton Bragg, detained Destin, fearing he had been actively trading with the enemy, so they could move him away from the East Pass.
A member of the militia writing home recounted the mission: “Our Captain received orders from headquarters to move Captain [Leonard] Destin, who is supposed to have carried on trade with the enemy from East Pass.”
The militia descended upon the Destin homestead, rounding up Leonard and his wife, Martha, who was 26 at the time. The couple was forced to take their four children—the youngest, Leonard Junior, being just 13 months old—on a journey to Freeport, where they had been married a decade earlier.
The climax of this ordeal arrived on August 20, 1861, when Captain Billy McPherson of the Walton Guards sent a formal report to General Braxton Bragg. The report confirmed the action: Destin had been moved to Freeport, and one of his hired hands had successfully escaped on a Union ship.A Community’s Mercy
Despite the allegations of “trading with the enemy”—a charge that could have led to dire consequences—the local rebels ultimately chose restraint. Executing a neighbor of over a decade who was deeply integrated into the local community would have been a significant blow to the militia’s morale and public standing. Instead, Captain McPherson opted for the more moderate course of relocation, sparing Destin from further retribution.
While this event was but one chapter in the long and complex history of the Emerald Coast, it serves as a stark reminder of how the grand, sweeping lines of the Civil War were drawn right through the front yards of families like the Destins, forcing difficult choices and lasting consequences in a rapidly dividing nation.
