The historical background to the Battle of Olustee began with Florida's secession from the Union in January, 1861. Despite its small population and lack of resources, Florida was an enthusiastic member of the Confederacy, at least in the early stages of the war. The state provided some 15,000 men to the Confederate armies, with perhaps 5,000 failing to return. Most Florida regiments served outside of the state, with the Florida Brigades in both the Army of Tennessee and the Army of Northern Virginia earning accolades for their valor.
Florida itself was not considered of strategic importance by either side during the war. The state was underpopulated, had no industry worthy of note, and was isolated from the other states of the Confederacy. As the war progressed, however, Florida did become valuable to the Confederacy as a source of much-needed beef, leather and salt. Extensive salt works were established along Florida's coast, with seawater being boiled down for its valuable content. The Union navy mounted numerous expeditions to destroy these works, but the industry continued until the end of the war. The ranges of central and south Florida, meanwhile, provided tens of thousands of cattle, desperately needed by the main Confederate armies. The demand for Florida beef became even more critical in 1863, following the Confederate defeat at Vicksburg which cut off supplies from Texas and Arkansas.
While no major battles on the scale of those fought in Virginia and elsewhere occurred in the state, Florida was the scene of a surprising amount of military activity. Fort Pickens at Pensacola, Fort Taylor at Key West, and Fort Jefferson in the Dry Tortugas remained in Union hands throughout the war, and northern forces permanently occupied Fernandina and St. Augustine early in 1862. Jacksonville was destined to be occupied four separate times by Federal forces. Key West was an important supply station for the ships on the blockade, and the coastal areas held by union troops served as bases for raids into the interior. As the war progressed, and hopes for a southern victory faded, many Floridians displayed a growing anti-war or pro-union sentiment. By 1864, large sections of the state. were essentially a no man's land, under the control of neither Confederate nor Union forces. Florida became a haven for Confederate deserters and those avoiding conscription. Ultimately, two regiments of Union cavalry were organized in Florida from loyal or disaffected elements of the population.
In early 1864, Union forces mounted their largest military operation in Florida, an expedition that culminated in the Battle of Olustee. Both political and military considerations played a role in the campaign. 1864 was a presidential year, and various factions within the Republican Party hoped to organize a loyal Florida government in time to send delegates to the Republican nominating convention. Treasury Secretary Salmon P. Chase was particularly intrigued with this possibility. Chase's protege Lyman D. Stickney, the Union Tax Commissioner for Florida, lobbied hard for an increased Federal military presence in the state. President Lincoln became aware of Chase and Stickney's machinations, and Lincoln himself hoped to see a loyal Florida government returned to the Union under the terms of his December, 1863 Reconstruction Proclamation.
In addition to the political objectives, legitimate military concerns also played a role in the decision to occupy East Florida. Major General Quincy Gillmore, commander of the Union Army's Department of the South, wrote in a January 31, 1864 letter that the expedition was designed, in addition to the political objectives:
"First: To procure an outlet for cotton, lumber, Timber, Turpentine, and the other products of the State. Second: To cut off one of the enemy's sources of commissary supplies. He now draws largely upon the herds of Florida for his beef... Third: To obtain recruits for my colored regiments...."
By early February 1864, General Gillmore had received approval from Washington regarding his plans to occupy Jacksonville with a large force and to extend Federal operations over much of northeast Florida. About 6,000 troops from Gillmore's Department of the South were selected for the operation. Most of these men were currently stationed along the South Carolina coast as part of the Union operations against Charleston. Gillmore placed Brigadier General Truman Seymour in actual command of the expedition.
The Union troops landed at Jacksonville on February 7th, and quickly gained control of the town. On the evening of February 8th, the Federals attacked and captured the Confederate positions at Camp Finegan and Ten Mile Run, located west of Jacksonville. Over the next several days, Union mounted forces advanced as far west as the outskirts of Lake City, some fifty miles from Jacksonville. Another smaller raid was made southward and captured Gainesville on February 14th, after which the Union troops involved withdrew to join the main force. This raid should not be confused with another Union attack on Gainesville in August of the same year, which resulted in a Union defeat. Meanwhile John Hay, President Lincoln's private secretary, arrived in Florida to begin taking oaths of allegiance from Florida unionists as a preliminary step in organizing a loyal state government. To this point, the Union occupation of East Florida seemed to be progressing according to plan.
The Confederate troops in Florida had few resources with which to stop the Union invasion. Following Union successes in Tennessee in early 1862, the majority of the southern forces in Florida had been withdrawn from the state and sent to more vital theaters of the war. By early 1864, Only a few units, mostly poorly equipped and with little combat experience, remained in Florida. The Confederate commander of the District of East Florida was Brigadier General Joseph Finegan, a native of Ireland who had served in the pre-war U.S. Army as an enlisted man, and who had been prominent in Florida politics and the railroad industry before secession. At the time of the Federal landings, Finegan only had about 1,500 troops to defend his District, which included the portion of Florida east of the Suwannee River. He immediately called for reinforcements from General Pierre Gustave Toutant Beauregard, the flamboyant but competent commander of the Department of South Carolina, Georgia, and Florida. From his headquarters at Charleston, Beauregard directed the transfer of troops to Florida from both South Carolina and Georgia. The Confederate movements were hampered by the fact that no direct rail link existed between Florida and the other states of the Confederacy. Southern soldiers had to disembark from trains in South Georgia, and then march overland until they reached Lake City, Madison, or other collection points along the railroads of Florida.
While Beauregard sent reinforcements to his aid, Finegan did what he could to hinder the Federal advance. A Confederate rearguard fought several skirmishes in an attempt to delay the invaders and Finegan concentrated the few troops he had at Lake City. By February 11th, Finegan had assembled about 600 troops at that location, enough to repel a minor Union cavalry raid made against the town. Over the next week larger numbers of Confederate reinforcements arrived. Among them were Brigadier General Alfred H. Colquitt and his brigade of battle-hardened Georgians, which had been serving in South Carolina. Colonel George Harrision also arrived with additional troops. By the time of the main Union advance on February 20, the Confederate force facing them numbered slightly more than 5,000 men.
While the Confederates were being reinforced, the Federal commanders were bickering over their next movement. Apparently, no firm decision had been made as to how far westward the Union advance should be undertaken. Some argued that it would be necessary to occupy Lake City, and perhaps to advance all the way to the Suwannee River to destroy the railroad bridge at that location. Even Tallahassee itself was mentioned as a possible target for a Union raid. Truman Seymour wrote a pessimistic letter to Gillmore on February 11th, stating that he was "convinced that a movement upon Lake City is not in the present condition of transportation, admissible." He further argued that Unionist sentiment in Florida was less than the Federals had been led to believe, and that "...the desire of Florida to come back [into the Union] now is a delusion." Seymour recommended withdrawing all troops from the interior of the state and maintaining garrisons only at Jacksonville and perhaps, Palatka. Upon receipt of Seymour's correspondence, Gillmore ordered that Seymour concentrate his forces at Baldwin "without delay."
The two Union generals met in Jacksonville on February 14th, to discuss future operations. Gillmore ordered that defensive works be constructed at Jacksonville, Baldwin, and Barber's Plantation, and that no advance be made without his consent. Gillmore left Florida the next day, returning to his headquarters at Hilton Head, South Carolina. He appointed Seymour commander of the newly-created District of Florida.
Within several days after Gillmore's departure, Seymour's confidence about the expedition seems to have returned. Seymour informed his superior that he now intended to advance to the Suwannee River to destroy the railroad bridge there. "By the time you receive this I shall be in motion," he declared to his shocked superior. Gillmore dispatched an officer to stop Seymour, but the Battle of Olustee occurred before he reached Florida. It is not known exactly why Seymour suddenly reached the decision to advance, but by February 19th he assembled his troops at Barbers Plantation in preparation for a movement westward the next day.
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