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Brooksville Raid helped Union in Civil War 150 years ago

Capt. Leroy G. Lesley led about 60 to try defending the county.
Capt. Leroy G. Lesley led about 60 to try defending the county.
Published Jul. 10, 2014

BROOKSVILLE — Every January, a couple of thousand Civil War re-enactors gather at Spring Hill to commemorate the area's only notable military action during the war. But while the grand spectacle known as the Brooksville Raid — with its legions of blue- and gray-coated soldiers firing barrage after barrage of rifle and cannon volleys — might make for fascinating battle theater, it doesn't exactly square with historical fact.

The original skirmish that brought the two adversaries face to face on Hernando County soil — 150 years ago this week — lacked the epic battlefield aura of its modern-day re-creation and, according to Florida Civil War history buffs and authors Jeff Cannon and Keith Kohl, more resembled a drawn-out game of cat-and-mouse.

Cannon and Kohl, who have spent years researching military archives and first-person accounts of the skirmish, concluded that while the six-day sacking of the agricultural community around Brooksville played no significant role by itself, its objective as a larger effort to systematically deprive the Confederacy of food and supplies ultimately helped end the Civil War.

During the war, from 1861 to 1865, Hernando County served as a vital resource for the Confederacy by providing cotton, salt and cattle, much of which was shipped over the Gulf of Mexico from the small coastal community wharf that is now Bayport. With no large-scale Confederate troops stationed locally, defending the county from Union invasion was left to a small volunteer "home guard" whose functions included guarding cattle drives northward and coordinating protection for blockade runners operating out of Bayport.

Led by Capt. Leroy G. Lesley, a preacher and rancher who served the United States during the Seminole Indian wars, the home guard included regular soldiers, as well as old men and young boys who served largely as pickets for the defenders — a total of about 60.

Although the county's population center of Brooksville escaped Union invasion, Bayport, like many other ports on Florida's west coast, was under attack often during the latter part of the war. By 1864, the port had been all but abandoned by members of the local militia, who upon leaving removed the two defensive cannons that had been installed two years earlier.

By that point, the war had taken a stiff toll on local residents. In addition to suffering through two bad crop years, much of the area's cattle was being ushered north to Gainesville to support the war effort. Many residents who had not signed up to be soldiers became either detached sympathizers of the cause or tried their best to ignore the escalating discomforts of the conflict.

In his online essay, The Brooksville-Bayport Raid and The Civil War in Hernando County, Cannon reprinted a letter to then-Florida Gov. John Milton from Hernando County Probate Judge Perry G. Wall outlining the desperate need of food for the area's indigent residents.

"If we have arrived at that point where it has become actually necessary to impress all the cows in the country to the support of any country, which are so necessary to the support of any country, then I say, God help us, for starvation must be inevitable," Wall wrote.

The launching in early July 1864 of a joint operation by the Union Army and Navy was meant to deal a crippling blow to the still-humming export of goods. A force of about 240 Union soldiers, including men from the 2nd Florida Cavalry plus a squadron made mostly of African-American soldiers, left Tampa bound for Anclote Key.

On July 7, the unit set out on foot toward Brooksville and was scheduled to arrive seven days later in Bayport to board ships anchored there. The next morning, the Union encampment discovered smoke from a campfire ahead of them to the north. The troops were immediately ordered to form ranks and prepare to march toward Brooksville.

An advance guard of 10 men under the command of Capt. Henry A. Crane overcame the Confederates, capturing seven men and nine horses. A brief skirmish led to the slight wounding of a Union guardsman, one of the few injuries recorded in the otherwise bloodless raid.

Cannon notes that the Union marauders quickly discovered they had a timeline challenge. Whether hindered by dense, swampy terrain or constant harassment from the local rebel guard, the troops decided to forgo entering Brooksville for fear of missing the appointed Bayport rendezvous.

Kohl believes the sparing of Brooksville might have also been because the town had been abandoned. Although official accounts differ, most historians agree that at least four Hernando plantations were burned by the soldiers on their way to Bayport. A large amount of the cotton, cattle and other goods headed for Confederate troops was captured as well.

Cannon, in his essay, noted that Union troops also threatened residents and looted private homes, including the residence of Capt. Thomas Benton Ellis, whose wife narrowly escaped being killed when the home was set on fire.

Although outnumbered nearly 3 to 1, Lesley's small platoon kept up its campaign to harass the Union regiment as it plodded toward Bayport while waiting for reinforcements to arrive from Tampa. It did little good.

On July 10, Union troops set up camp at the plantation of David Hope, the son of one of the county's earliest settlers. After feasting on fresh pork, corn and melons, they set fire to the home and its out buildings.

The next day, the enemy troops repeated their pillaging on other farms, including Lesley's own home.

Surprisingly, the skirmish produced only one death, a Union prisoner killed by Lesley, who in the darkness also wounded his son, John T. Lesley, whom he mistook for a Union soldier.

By late morning on July 13, the Union troops boarded their vessels waiting at Bayport and headed for Fort Myers. Meanwhile, residents left in the wake of the raid could only hope the enemy would have no more interest in invading the county.

The damage left behind was devastating, said Kohl, an avid Civil War re-enactor who participates annually in the Brooksville Raid re-enactment. He finds the Brooksville/Bayport battle a fascinating subject, not because of its military objective, but for the effect it had on the county's residents.

"I think it shows there was the thought that a skeleton defense would do in Hernando County, so they pulled out their resources and moved them elsewhere," Kohl said. "But a lot of people left the county afterward and never returned. And for that, it took a long, long time before things got back to any sense of normalcy."

Contact Logan Neill at or (352) 848-1435.