Tampa’s Leroy Lesley had adventurous time in Manatee

Second of two parts

When we last left off, the Rev. Leroy Lesley was able to return to his home and farm life. Unfortunately, the peace did not last long, and by 1855 he once again was called to the military life with the start of the Third Seminole War. Captain Lesley (now Captain – rather than Reverend) organized his own company, the Florida Mounted Volunteers, and set out for Fort Meade. Once there, he joined up with Captain William B. Hooker, and they took command of Pease Creek (Peace River) through the winter of 1855.

In the spring of 1856, Captain Lesley and his company were sent to Manatee to protect the settlers here after the Seminole attack on Braden Castle. Under the direction of Captain Lesley, the company traveled Manatee County, from Alafia to Fort Meade, but found little to no evidence of recent Seminole settlements. In his April 1857 assessment, he stated: “I have no hesitation in making the assertion that there are no Indians within the district assigned me.”

Captain Lesley continued his service pursuing Seminoles down to Big Cypress and eventually took command of the post at Fort Myers, where he stayed until May 1858, when the final round of Seminoles were sent away on the steamer Grey Cloud. During these pursuits, Captain Lesley faced many obstacles, but the Theodore Lesley Composition Book tells the story of how Captain Lesley narrowly escaped dying at the hands of Billy Bowlegs: “After the surrender of the Indian Chieftain, Billy Bowlegs, and while he was quartered near Tampa before he and his men were sent away he told this tale to G. grandfather, Capt. L. G. Lesley.

After a hot pursuit of a band of Indians headed by Bowlegs, G. grandfather and his men thought they had the warriors surrounded in a Bayhead. The men dismounted and searched thoroughly the heavy brush but discovered not one of the wiley savages. Bowlegs told with great enjoyment how he outwitted grandfather, an officer in the U.S. Army, by hiding under a log that Capt. Lesley stood on to see over into a clump of palmettos. He confessed openly that he would have shot him there if it would not have given away his hiding place to the other soldiers.”

At the conclusion of the Third Seminole War, Captain Lesley returned to family life until the Civil War began. He commanded a small garrison at Shaw’s Point in 1861 and in 1863, at the age of 56, Captain Lesley again raised his own company to fight for the Confederacy. This company was stationed in Brooksville with the responsibility to be a home guard, assist federal blockage runners and drive cattle to feed the Confederate troops. An incident occurred on one of Captain Lesley’s patrols that would later cause him to face investigation for war crimes, but it was eventually dropped due to lack of evidence. Captain Lesley also took part in helping Confederate Secretary of State Judah P. Benjamin in his escape through Manatee. Captain Lesley accompanied Benjamin through Hernando, Hillsborough and Manatee counties to ensure his safety. He also arranged Benjamin’s stay with Archibald McNeil at Gamble Plantation.

Captain Lesley once again returned to family life and became involved in politics in Hillsborough County, where he was elected tax assessor. Upon his death is 1882, Lesley was remembered as “one of the oldest, most respected and highly esteemed citizens of Hillsborough County.”

To learn more about the Manatee Village Settlement and Manatee County History, join us on March 25 at Manatee Village Historical Park at 1404 Manatee Ave. E. in Bradenton for our annual Heritage Days Open House. The event runs from 11 a.m. until 4 p.m. and includes the second annual HAIRitage Days Beard and Mustache Competition (including Fake Beard categories for women and children). Admission and parking are free, and contest participants have a $5 entry fee. For more information, visit www.manateevillage.org.

This story was originally published March 8, 2017 at 4:08 PM with the headline "Tampa’s Leroy Lesley had adventurous time in Manatee."