Biography from Benson J. Lossing in his Pictorial Field-Book of the Revolution [with minor edits]:
Richard Winn was a native of Virginia. He entered the service early and in 1775 was commissioned the first lieutenant of the South Carolina rangers. He served under Col. William Thomson, in General Richardson's expedition against the Tories, in the winter of that year. He had been with Thomson in the battle on Sullivan's Island. He afterward served in Georgia and was in command of Fort McIntosh on the north side of the Santilla River. He was subsequently promoted to colonel and commanded the militia of Fairfield District.
He was with Sumter at Hanging Rock, where he was wounded. He was active during the remainder of the war and at the conclusion was appointed brigadier and finally a major general of militia. He represented his district in Congress from 1793 to 1802. He moved to Tennessee in 1812 and died soon afterward.
Winnsboro, the present seat of justice of Fairfield District, was so named in his honor, when he was colonel of that district in 1780.
From "History of Fairfield County, South Carolina," by Fitz Hugh McMaster, 1942 [with minor edits]:
Richard Winn was a native of Virginia; at the beginning of the Revolutionary struggle he entered into the regular service of this State. Having acquired glory in the battle at Fort Moultire, he was sent to the Georgia frontiers, and commanded a company at Fort. St. Illa. The service was a most perilous one and he was selected for it on account of his superior merit as an officer. Shortly after his arrival at the fort he was attacked by a strong force of Indians and Loyalists; these he beat off for two succeeding days; on the third he surrendered with honorable terms to Major General Prevost, at the head of a considerable regular force supported by his allies.
Capt. Winn returned to Fairfield after his defeat if can be properly called one, and took command of a regiment of refugee militia. He was in several battles and the success of the affair of Huck's defeat in York [Williamson's Plantation], and the Hanging Rock in Lancaster greatly depended upon his heroic exertions. At the latter place, said the great and good General Davie, who commanded a regiment of cavalry, when the firing had become pretty warm, Winn turned around and said: "Is not that glorious?" He was wounded here and borne off the field about the time the enemy effected his retreat. On his recovery, Winn continued to affort General Sumter his able support, and ceased not to serve his country whilst a Red Coat could be found in Carolina. He was a true patriot, and perhaps, fought in as many battles in the Revolutionary War and with as firm heart as any man living or dead. Such a man ata such a time was invaluable to his country.
After the return of peace he was elected brigadier general, by the Legislature of this State and rose to the rank of Major General in the militia. He also served as a county-court Judge with much ability, and filled a seat for many years in the Congress of the United States. In addition to his other claims to the lasting gratitude of his country, General Winn was a perfectly honest and honorable man. He removed to Tennessee in 1812 and died a short time after.
Gen. Richard Winn was from the old Dominion. He immigrated to Carolina a considerable time before the War, and served as a clerk in the counting-house in Charleston for some years. He then took a position in the Virginia Colony in Fairfield, where he found many old friends and kindred. Here he followed the business of a land surveyor until just before was whitened with the canvas of the British ships, and lit up with red coats. He recieved the appointment of First Lieutenant in Capt. Woodward's company of Rangers, and served on Sullivan's Island when Sir Peter Parker made his formidable attack on the palmetto fort. The enemy having withdrawn for a time from that quarter, gave the commanding General time to look about him, and attend to the interest of the country at other and distant points.
He received advices that the Loyalists and Indians, backed by a few British troops, were committing sad havoc in the most Southern part of Georgia. The county was totally defenseless. Fort St. Illa and Fort Barrington had been both abandoned. It was desirable that the former should be placed in good repair & thoroughly garrisoned with a view to hold the enemy in check, and restrain his wanton depredations. The general promised the command in this important service to any officer of the rank of Captain who could raise eighty volunteers for the purpose. Winn was now Captain, but he was not the first to beat up for volunteers; several Captains attempted to do so, and failed. Capt. Winn at length raised his flag, and ordered out his music. In less than 25 minutes his number was made up. He made no unnecessary delay; he & his men were speedily equipped and mounted, and they took up the line of march for their distant point of destination.
On approaching Fort St. Illa, a considerable body of the enemy were discovered. He divided his force into two equal parts; one he left to find its way to the fort, and to preserve the military stores committed to its charge. The other he put himself at the head of, and ordered a charge upon the enemy. He declined returing the Whig fire, and set off with speed for his flotilla in the river eleven miles below. Winn killed 14 of them on the chase, wounded as many more, and recovered all the property which they had gaterhed in the plundering excursion into the country, with a quantity of arms and ammunition. He returned to his friends well rewarded for his long race, and the slight peril incident to his enterprise.
Capt. Winn found the fort in an utterly ruined condition, and set about constructing a new one much larger than the old one. He took the axe & spade himself, and there were no lookers-on in camp. A strong block-house, inclosed with hugh palasades, soon sprang up sufficient to affort protection against any number of small arms. The fort was scarcely completed when a large body of Loyalists and Indians, sustained by a few regular troops, made their approach. A flag was sent in to demand the instantaneous surrender of the fort. The Captain knew the strength of his position, and the character of the brave men under his command. He declined the surrender demanded, and preparded for his defense, as it was evident, against fearful odds. The firing commenced on both sides, and was kept up almost incessantly for near three days. Many of the enemy climbed up into the neighboring trees with a view to fire over the pickets into the body of the fort; but the block-house rendered their efforts unavailing, and many a one never descended alive from their high nest in the tree-tops.
On the evening of the third day of the fight, Gen. Prevost came up from Augusta with three pieces of cannon and a strong regular force. A flag demanding ain unconditional surrender arrived speedily at the fort. Winn saw his case now was a hopeless one, as he had no power to resist artillery. He therefore determined to surrender, but insisted on certain terms to be settled by articles of capitulation. The Commissioners were appointed to draw up the terms, to which Maj. Genl. Prevost and Capt. Winn set their hands - they were very liberal and favorable to the Americans. The gates of the fort were then thrown open, and many of Prevost's officers entered. It is said, that when he saw a Captain and a few ragged militia who infliced on his motly army damage to an unprecedented amount, he groaned in spirit.
On first arriving at the fort, the Americans had turned their horses into the range, many straggled off, and not a few fell into the hands of the enemy. Three-fourths of the men had to march on foot to their distant homes in middle and upper Carolina. As the force under Capt. Winn at Fort St. Illa were three-fifths of them soldiers in his company of Rangers, the surrender operated as a dissolution of the company.
As soon as he was exchanged, he was appointed Colonel of the Fairfield Whig regiment, marched at its head, and joined Genl. Sumter. Except when detailed on special duty, which was the case often, and in which he always acted effectually and heroically, he was always by his General's side, and participated in his principal battles. He was with him among many other trying occasions at the battle of Hanging Rock, where he received a wound through the body, which was near proving fatal. In that battle no man quailed - every American behaved like a veteran. Cornwallis was heard to say that no battle fell heavier on the British, considering the numbers engaged, the Battle of Bunker Hill excepted. Recovering slowly from his dreadful wound, the Colonel returned to his command, and was always at his post of duty. He never returned to the delights of home, or the business of civil life as long as there was a Briton in the land, or a Loyalist persisting in his rebellion.
On the return of peace he visited his friends, and resumed his long abandoned labors. He shortly afterwards married, settled a farm, purchased slaves and stock, and went to work to provide for his family. In 1788, he was appointed U. States Superintendent of Indian Affairs for the Creek (Southern Indians) Nation. He was called several times to serve in the Legislature, and presided in the County Court whilst that system was allowed to continue. On the reorganization of the militia in 1796, he was elected a Brigadier General and some years after Major General, of the upper division. About 1783 he beat Gen. Sumter for Congress, but was beaten in turn by Sumter at the ensuing election. About 1796 (1801-L.C.D.) Sumter was elected to the US Senate and Winn succeeded him as a Representative, and held that high appointment by many successive elections, down to 1812. He was twice very fully opposed, and at every other was chosen without opposition. He belonged to the Jefferson party in politics, and never during the whole course of his public life was he suspected of a change in sentiment. Gen. Winn was a highly respectable member, but no speaker. One efficient speech, however, he made about the time of the declaration of the War of 1812. The bill looking to the war, providing for an increase of the army, made provision for calling into the field a great many volunteer regiments. A Federal member ridiculed the idea of opposing British veterans with raw volunteers. Winn was stung by his remark, and addressing the Speaker replied to him that "he had commanded volunteers, and had seen them meet British veterans who considerably out-numbered them, and had seen them beat British veterans in the open field. I will give that gentleman a picked regiment of his favorite veterans, and will put myself in command of a regiment of Volunteers, we will have a meeting, and if I don't flog him ('popping his hands emphatically) my head for it." The Federal member evidently displayed signs of discomfiture, and the Republicans openly congratulated Winn for his Triumph.
Gen. Winn had the usual weakness of putting his hand to paper as security, and as is usual generally had the money to pay. Between 1795 and 1810, he paid security debts to the amount of $50,000. In his long absences from home, his overseers did what was good in their own eyes - that is, never to consult the good of the employer. His plantation was unproductive of profits, and his circumstances were not prosperous. He sold his lands at good advantage, removed with an aching heart from his ancient seat, and a country he loved, for a body of lands he owned on Duck River in Tennessee. Here, after some years in the depth of the solitude, and amidst strangers, he breathed his last at a good old age. Gen. Winn was upwards of six feet in height, and indifferently well formed. His countenance was noble and majestic, and beamed with the warmth of benevolence and kindness. His port was noble, and his manners dignified and elegant.