In the early morning hours of May 17, 1865, off the far southwestern cape of mainland Florida, pickets stationed there by Union General John Newton intercepted a small vessel bound for Cuba. That promontory, jutting out into the Gulf of Mexico, Cape Sable. Today, the cape is preserved, not for its connection to the Civil War, but within the confines of Everglades National Park, and the critical habitat of the Cape Sable Seaside Sparrow.
Lieutenant J.J. Hollis of the 2nd Florida Cavalry (USA) had been sent with a detachment to Cape Sable on May 9 with the sole purpose of “to intercept any parties who might be making their escape from the Confederacy.” The intervening days was spent in an area filled with mangroves, hardwood hammocks, and dense vegetation, a remote area of Florida even in today’s world. The intelligence gathered and shared by Union authorities in the state of Florida though would ensure their wait in this tropical location would not be in vain.
At 2:30 a.m. the occupants of this boat, deemed “persons of importance” by the United States military were taken into custody. This gleaned hope for the operation, which both the army and navy were conducting in Florida and along her many miles of coastline as hostilities were winding down was the was to ensnare fleeing high-profile former Confederates
One week after Confederate president Jefferson Davis was captured near Irwinsville, Georgia, the armed forces of the United States was still on the look-out for the likes of Judah Benjamin, the last Secretary of State in the Davis cabinet and John C. Breckenridge, former vice president of the United States and last Confederate Secretary of War. Both were fleeing and both also happened to be in the state of Florida on May 17.
Initially, according to Acting Volunteer Lieutenant Edward Conroy, in his report from the USS Union to Secretary of the Navy Gideon Welles, mentioned what transpired on that May day:
“General Newton commanding the army forces at Key West, received information that his pickets at Cape Sable, [Fla.], had captured a boat containing 7 white persons and 1 colored, all armed, and to appearance, persons of importance. They had embarked at Crystal River, pulling and sailing along the coast of Florida during the night and secreting themselves during the day. Their object was to get to Havana…Not having been received at Key West, it is not known who they are. Their conduct looks suspicious and leads to the supposition that they were men of importance in the so-called Confederacy, and that many of the names given are fictitious. It is thought Breckenridge and Mallory are among them.
However, the people floating on that boat, were not these luminaries of Mallory and Breckenridge. Although Mallory hailed from Key West and had left Richmond with Davis, he had quit the southward movement in Georgia to seek out his family who were refugees there. He was taken captive by Union forces in La Grange, Georgia on May 20.
A few of the men on that boat were “persons of importance” of the “so-called Confederacy.” One of the individuals was Thomas A. Harris, former Missouri State Guard brigadier general who had fought at the First Battle of Lexington, Missouri in September 1861, then became a congressman representing Missouri. He did not win reelection in 1864 but embarked on a covert international mission, besides trying to smuggle supplies into the blockaded Confederacy, along with fellow captured shipmate Richard S. McCulloch.
The plan that had been concocted was to attack United States shipping interests and possibly foreign vessels that were sailing toward United States ports. Their goal was to place fire bombs or other explosive devices on board these ships and called for establishing pro-Confederate operatives at these foreign ports. The Confederacy fell before they could fully realize this clandestine warfare plan.
Unfortunately for the naval and army forces spread throughout south Florida, Benjamin and Breckenridge would both evade authorities and spirit their way out of the country, Breckenridge through Cuba and eventually to Canada and Benjamin by way of the Bahamas and to a permanent exile in Europe.
Harris, the most notable Confederate captured on May 17, would return to Missouri, worked in a life assurance company, moved to Texas, before finally settling in Kentucky. Which also happened to be where the person he was hoped to be by Union authorities, John Breckenridge, was from and finished his days.
www.peweevalleyhistory.org (The Harris Years)
Official Records of the Union and Confederate Navies, ser. 1, v. 17, page 853
An Honorable Defeat: The Last Days of the Confederate Government by William C. Davis
Flight into Oblivion by Alfred Jackson Hanna