Union Forces Commanded by: Brig. Gen. Truman Seymour
Confederate Forces Commanded by: Brig. Gen. Joseph Finegan
**Missing and Captured
Conclusion: Confederate Victory
Early in the morning of February 20, Brig. Gen. Truman Seymour's army left Barbers' Station and moved westward towards Lake City. Because of the necessity of posting garrisons at Jacksonville and elsewhere, the Union force consisted of between 5,000 and 5,500 men. The small army was divided into three brigades of infantry, one brigade of mounted troops, and an artillery support unit.
The Federals advanced in 3 columns along the Lake City and Jacksonville Road, which ran roughly parallel to the Florida Atlantic and Gulf-Central Railroad. The Union cavalry was in the vanguard, followed by the slower-moving infantry. By mid-day, the Federals had reached Sanderson.
In the early afternoon of February 20, a few miles west of Sanderson, the advance elements of the Union cavalry engaged a few Confederates that appeared to their front. This skirmishing was maintained for several miles, with the Federals driving the Confederates westward towards the railroad station at Olustee. Confederate resistance intensified as the Federals neared Olustee.
After the fight at Lake City on February 11, Brig. Gen. Joseph Finegan moved his troops to Olustee Station. There, the Confederates found one of the few defensible locations in the area where the railroad passed through a narrow corridor for dry ground that was bordered by impassable swamps and bays to the south and a large body of water to the north. The Confederates built strong earthworks and waited for the Union advance. When Finegan learned of the Federals approach on February 20, he ordered his cavalry forward to find and engage the Union troops and to drive them towards his main line. Unfortunately for Finegan, the fighting east of his main line intensified, forcing him to send out additional help to those already deployed. A major fight soon developed about two miles in front of the Confederate line.
As the fighting grew bigger, both Finegan and Seymour fed more and more troops into the fight. By midafternoon the fighting has escalated into a major battle. The battle threatened to turn rapidly into a rout for the Federals. While Col. Hawley was positioning the 7th New Hampshire, a wrong command was given and the unit fell into confusion. The 7th soon collapsed, with some men running to the rear and others milling about in a disorganized mob. The collapse directed Confederate attention towards the 8th U.S. Colored Infantry, which occupied the left of the Union line. The 8th was an untried unit, having been organized only several months before. Col. Charles Fribley tried to steady his men, but he soon fell mortally wounded. The raw troops of the 8th held their ground for a time, suffering more than 300 casualties. Finally, however, they retreated in some confusion, leaving the Confederates in virtual command of the battlefield.
With the dissolution of Hawley's Brigade, Colquitt ordered the Confederate forces to advance. Since the beginning of the battle, Finegan had sent additional units to Colquitt's support, so by now the Confederate lines stretched for about 1 mile, north to south. Col. Harrison commanded the Confederate left, and Colquitt the right, although the units of their brigades were somewhat intermingled.
To stop the Confederate advance, Seymour hastily ordered more troops forward. The Union stopped the Confederate advance, and the battelines stabilized for a little while. The Union commander would later be criticized for reacting slowly to an increasingly dangerous situation, and for deploying his forces piecemeal into the battle. The Union lines were bordered by swamps on both flanks so there was little room to maneuver, and the field itself was wide open and with very little cover for his troops to use.
The fighting during this middle part of the battle was particularly severe, with each side suffering heavy casualties. During this fight, the Confederates captured several Union artillery pieces and threatened to overwhelm their infantry. Although the Federals were under intense pressure, at a critical moment the surging Confederates began running low on ammunition. Men searched their wounded and dead comrades to obtain additional rounds, but still the Confederate fire slowed down. Several regiments held their place in line despite being completely out of ammunition. After what seemed to be an interminable delay, ammunition was brought forward from Olustee, along with the remaining reserves. Finegan also reached the battlefield at about this time.
With the arrival of these reinforcements, the Confederates began advancing again. By late afternoon, Seymour had realized the battle was lost. To cover his retreat and prevent a rout of his army, he sent forward his last reserves. The Confederates were stopped for a brief time, enabling Seymour to begin withdrawing his other forces.
By dusk, the Union forces had begun their long retreat back to Jacksonville. Many wounded and a large amount of equipment had to be abandoned in the hasty retreat. Fortunately for the Federals, the Confederate pursuit was poorly conducted, enabling most of the Federals to escape. The Confederate calvary, led by Col. Caraway Smith, was criticized for its lackluster performance. That night the Federals retreated all the way back to Barbers, where they had begun the day. By February 22, Seymour's battered army was back in Jacksonville.
The casualties at Olustee were staggering compared to the numbers that fought there. Each side had about 5,000 men present. Casualties equaled to about 40% for the Federals and 20% for the Confederates.
For the Union, the casualty percentage was among the highest of the war, and Olustee ranks as the third bloodiest for the Union when comparing the casualties to the number on men engaged. Letters and diaries from the men involved indicate that the battle was the equal of, if not worse than, the savage fighting a number of the veteran regiments had experienced in the campaigns in Virginia or the Western theater.
A regrettable episode in the aftermath of the battle was the apparent mistreatment of Union black soldiers by the Confederates. Contemporary sources, many from the Confederate side, indicate that a number of black soldiers were killed on the battlefield by roaming bands of southern troops following the close of the fighting.
The Olustee defeat ended Union efforts to organize a loyal Florida government in time for the 1864 election. The Federals were somewhat more successful in meeting the expedition's military objectives. Jacksonville remained in Union hands until the end of the war, open for trade with the north; the operation had undoubtedly disrupted the supply of Florida cattle and other foodstuffs to the rest of the Confederacy; and the increased area of Federal control made it easier for Florida blacks to reach Union lines and for recruits to fill the ranks of northern military units. Of course, all of these objectives could have been met simply by the occupation of Jacksonville and without the nearly 2,000 casualties suffered at Olustee.