Heather Cox Richardson
Monday was the anniversary of the Battle of Olustee, the largest Civil War battle fought in Florida. Although few people today have even heard of it, Olustee was crucial in convincing Civil War era Americans to accept black freedom.
On February 7, 1864, Federal troops landed in Jacksonville. Carving Florida off from the rest of the Confederacy had several obvious advantages. First, the Confederacy was hurting for food, especially cattle. When the Union took the Mississippi River, it cut off the Texas herds from the rest of the South. The cattle herds in Georgia, Alabama, North Carolina, and South Carolina could not fill the gap. If the Union could cut the lines for moving the Florida cattle that still fed the South in 1864, it would be closer to starving the South into submission. One general estimated in 1864 that 20,000 head of cattle and 10,000 hogs a year went from Florida to feed the Southern armies.
President Lincoln also wanted to reorganize Florida out from under the Confederacy as a free state much as he was trying to do in Louisiana. Opponents carped that he was trying to get Florida back into Congress so he could count on more electoral votes in the 1864 election, although there were obvious reasons to want Florida back on the Union side even without the president’s reelection fight looming on the horizon.
Finally, an excursion into Florida promised to attract black recruits to fight for the Union. And in 1864, new soldiers would be quite welcome to the battle-thinned Union ranks.
Brigadier General Truman Seymour, the head of the expedition, had strict orders not to move far from Jacksonville. Instead, Union troops under Colonel Guy V. Henry of the Fortieth Massachusetts mounted quick raids that destroyed supplies and reconnoitered the Confederate army. Their operations among the poor and dispirited people were successful and relatively painless: they suffered few losses.
It was perhaps the ease of the raiding to that date that made General Seymour decide on February 17 to march his 5,500 men 100 miles west to destroy the railroad bridge over the Suwanee River. Seymour did not know that Confederate officers had surmised the danger to Florida and had moved troops quickly to prevent Union troops from gaining a foothold in the interior. Five thousand Confederates under Brigadier General Joseph Finegan were encamped on the road Seymour’s men would take, near the railroad station at Olustee, about fifty miles from Jacksonville.
When the two armies came together in mid-afternoon on February 20, Seymour threw his men in without much forethought, apparently believing he was up against the same ragtag fighters Henry had been smashing for weeks. But Finegan’s men were experienced troops. They trained their cannons and held their ground. The Union lost more than 1800 men to the Confederacy’s 950. Most of the surviving Union soldiers ran from the field to hightail it down the road back to Jacksonville.
The Union rout did not turn into a panic solely because the remnants of the Massachusetts 54th and the 35th U. S. Colored Troops held the Confederates back to cover the retreat. The soldiers of the Massachusetts 54th had earned their reputation for bravery in the assault at Fort Wagner, near Charleston, South Carolina the previous July. At Olustee, the black soldiers from the 54th and the 35th held their ground until past dark, enabling the white troops to get safely out of range, before they received their orders to move back toward Jacksonville.
Few people now remember Florida’s major Civil War battle, but it made a searing impression on President Lincoln. “There have been men who have proposed to me to return to slavery the black warriors of Port Hudson & Olustee to their masters to conciliate the South,” he told visitors in August 1864. “I should be damned in time & in eternity for so doing.” (AL to Alexander W. Randall and Joseph T. Mills, August 19, 1864, in Roy P. Basler, Collected Works of Abraham Lincoln, volume 7, pp. 507.)
 The New York Times noted that the Colonel Henry had three horses shot out from under him during the battle, but was himself unhurt. His luck would not hold. Henry continued to serve in the army until 1892. He fought in the Apache campaign before joining the Sioux Wars. He was shot in the face in the Battle of the Rosebud, losing part of his cheek and one eye. He later led the Ninth Cavalry in the events surrounding the Ghost Dance and Wounded Knee Massacre.