February 19, 1864 – Federal forces launched an expedition to conquer Florida, while Confederates scrambled to put up a defense.
Major General Quincy A. Gillmore, commanding the Federal Department of the South, had been assigned to invade Florida. Gillmore was to impose President Abraham Lincoln’s “Ten Percent Plan” by registering 10 percent of the state’s voters so they could elect delegates to form a new Unionist state government. Lincoln had dispatched his secretary, John Hay, to register the 10 percent as Federal troops operated in Florida.
Rear Admiral John A.B. Dahlgren, commanding the South Atlantic Blockading Squadron, granted Gillmore’s request for naval support by providing the screw steamers U.S.S. Ottawa and Norwich to transport troops up the St. John’s River. The gunboats U.S.S. Dai Ching, Mahaska, and Water Witch would also support the army expedition.
Gillmore assigned Brigadier General Truman Seymour, an officer familiar with Florida as a veteran of the Seminole Wars, to lead the division in the field. Seymour had four objectives:
- Help restore Florida to the Union under Lincoln’s “Ten Percent Plan”
- Secure the St. John’s River for Federal trade
- Liberate slaves and recruit them into the Federal army
- Destroy Confederate supply lines and any materiel–primarily beef and saltworks–considered useful to the Confederate war effort
Gillmore instructed Seymour to land his troops at the state capital of Jacksonville and then move west to Baldwin, “and, if possible, beyond.” Gillmore told him that the Confederates probably had a “small force of infantry and a battery between Jacksonville and Baldwin.” Seymour was to advance no farther than Lake City.
General P.G.T. Beauregard, commanding the Confederate Department of South Carolina, Georgia, and Florida, learned that Seymour was preparing an expedition and correctly guessed that his target would be Florida. Beauregard dispatched troops under Brigadier General Alfred H. Colquitt to reinforce Brigadier General Joseph Finegan, who commanded the District of East Florida.
Seymour’s Federals left Hilton Head, South Carolina, aboard 20 transports on the 5th. The force consisted of 5,500 men in three infantry brigades, two cavalry regiments, and four artillery batteries. The transports and gunboats moved up the St. John’s River and landed at Jacksonville two days later. The city had been virtually destroyed by previous Federal occupiers.
The Federals debarked and quickly captured about 100 remaining Confederates. Hay informed them that if they swore allegiance to the Union, they would be freed and allowed to help form the new state government; if they refused, they would be sent to northern prison camps. Hay said, “There is to be neither force nor persuasion used in this matter. You decide for yourselves.”
Hay received the signatures of about half the prisoners, along with several city residents. During his stay at Jacksonville, Hay invested in real estate as part of his plan to become a congressman in the new state government.
Seymour’s Federals also seized eight cannon and a large amount of cotton awaiting blockade runners for shipment. The Norwich trapped the Confederate steamer St. Mary’s on McGirt’s Creek, forcing the Confederates to burn and abandon her. The Federals prepared to head west along the Florida, Atlantic & Gulf Central Railroad, toward Baldwin and the Suwannee River.
Sporadic skirmishing occurred over the next few days, with the Federals arriving at Baldwin on the 10th. To Seymour’s disappointment, the civilians expressed none of the Unionist sentiment that the Federal high command expected. Moreover, Federal cavalry under Colonel Guy V. Henry probed forward and discovered that Confederates were preparing to make a stand at Olustee.
Seymour reported to Gillmore, “I am convinced that a movement upon Lake City is not, in the present condition of transportation, admissible, and indeed that what has been said of the desire of Florida to come back (to the Union) now is a delusion.” Seymour recommended returning his force to Jacksonville, but Gillmore urged him to continue west to Sanderson, halfway to Lake City, and dispatched the 54th Massachusetts Colored Infantry as reinforcement.
The Federals advanced to Sanderson, where they destroyed vast amounts of public and private property. During this time, Gillmore left Jacksonville and returned to Hilton Head, where he arranged for supplies to be delivered to Seymour’s men. They were now in the unforgiving Florida country of stunted oaks, pines, and palmettos, and their only train had broken down. When Gillmore received word that Confederate cavalry might be threatening Seymour’s right flank, he ordered Seymour to fall back to Baldwin.
Seymour complied, but by the 16th, he was convinced that he could get to Lake City. He informed Gillmore that he intended to head there and destroy the railroad. He asked Gillmore to send him naval support on the Savannah River, adding, “I look upon this as of great importance.”
Stunned, Gillmore replied that there was no way he could arrange such support so quickly. He wrote, “You must have forgotten my last instructions, which were for the present to hold Baldwin…” Gillmore reminded Seymour that he (Seymour) had argued for returning to Jacksonville, but now he inexplicably sought to capture Lake City. He also informed Seymour that the Federal high command had no plans to operate in the Lake City region of Florida, making his proposed advance there pointless.
Meanwhile, Confederates stationed at Lake City observed the Federal movements and relayed them to Finegan. He reported to Beauregard that the enemy numbered at least 10 regiments. Beauregard responded, “Enemy’s forces should on no account be exaggerated. His regiments average 600 at most, composed largely of newly drafted men and recruits; not a match for one-half of our men.”
Finegan scrambled to build a defense line along the railroad near the small hamlet of Olustee, about 10 miles east of Lake City. He ordered his officers “to impress the required negroes and to collect such tools as might be procured from the surrounding plantations.” By the 19th, the Confederate defenses were not yet completed, but Colquitt’s Confederates had arrived to reinforce Finegan. Seymour’s Federals passed Barber’s Plantation and headed for the Confederate line outside Lake City.
Chaitin, Peter M., The Coastal War: Chesapeake Bay to Rio Grande (Alexandria, VA: Time-Life Books, 1983), p. 139; CivilWarDailyGazette.com; Denney, Robert E., The Civil War Years: A Day-by-Day Chronicle (New York: Gramercy Books, 1992 [1998 edition]), p. 366, 371, 373-74; Foote, Shelby, The Civil War: A Narrative: Volume 2: Fredericksburg to Meridian (Vintage Civil War Library, Knopf Doubleday Publishing Group, Kindle Edition, 2011), p. 900-03; Fredriksen, John C., Civil War Almanac (New York: Checkmark Books, 2007), p. 394-97; Long, E.B. with Long, Barbara, The Civil War Day by Day (New York: Da Capo Press, Inc., 1971), p. 462; Longacre, Edward G., Historical Times Illustrated Encyclopedia of the Civil War (New York: Harper & Row, 1986, Patricia L. Faust ed.), p. 545