James Winchester was born on February 6, 1752, in Carroll County, Maryland, near the present Westminster, the third child of William Winchester, Sr. , who came from England to Maryland about 1730, and of Lydia Richards, daughter of Edward Richards of Baltimore County, Maryland.
James was educated by tutors and in local schools.
In 1776 he enlisted in the Maryland Battalion of the Flying Camp, for service in the Revolution, and was promoted for bravery on the battlefield. At Staten Island, August 22, 1777, James was wounded and taken prisoner, being held for a year before he was exchanged. He was captured again at Charleston, South Carolina, in 1780, but was soon released. James as captain fought through the southern campaign under General Greene, were present at Yorktown in 1781, and then returned to Maryland.
He moved in 1785 to Middle Tennessee (then the Mero District of North Carolina) and settled on a large tract of land. James served in the North Carolina convention in 1788, and successively as captain, colonel, and brigadier-general of Mero District, becoming famous for his Indian campaigns. When Tennessee was admitted to statehood in 1796, he was elected state senator, and speaker of the Senate. In the years that followed he held numerous other local offices. Meanwhile, through farming, milling, and commercial transactions he grew wealthy, and built an imposing stone house on his plantation, "Cragfont. "
When war with England began in 1812, Winchester was appointed a brigadier-general in the United States Army, and placed in command of the Army of the Northwest, succeeding William Henry Harrison, but after some dispute as to seniority, Harrison was commissioned major-general and given the complete command. In an effort to protect the frontier, Winchester moved with the left wing from Fort Wayne to Fort Defiance, defeated one body of British and Indians, and constructed Fort Winchester. Moving on to Frenchtown, on the River Raisin in southeastern Michigan, he defeated another British force, but on January 22, 1813, was surprised by a force of some 2, 000 men, and almost his entire army was killed or captured. Winchester himself was imprisoned in Canada for over a year. After exchange, he was placed in command of the Mobile District. Following the defeat of the British at New Orleans, their fleet stopped off Mobile Harbor and on February 12, 1815, captured Fort Bowyer, but sailed away without attempting to take Mobile. When news of peace arrived, Winchester resigned and returned home.
In 1816 Robert B. McAfee, in his History of the Late War in the Western Country, accused Winchester of gross negligence and military incapacity in the River Raisin campaign. Winchester unsuccessfully demanded an official inquiry, and wrote a defense of his conduct in which he attacked General Harrison for failing to send promised reinforcements. The quarrel was bitter, but it seems that loose organization and impassable frontier roads, combined with negligence by both men, caused the defeat and massacre.
In 1819 Winchester was appointed commissioner to run the Chickasaw Boundary Line between Tennessee and Mississippi. It was his last official position. Through his remaining years he was active, intermittently, in business ventures and in the founding of Memphis, Tennessee, but mainly he lived in ease until he died on July 26, 1826, and was buried at "Cragfont. "
Probably in 1803 James Winchester married Susan Black, by whom he had fourteen children.
Robert Breckinridge McAfee was a Kentucky politician, and was the seventh Lieutenant Governor of Kentucky serving from 1824 to 1828.
George Washington Winchester was an American soldier.
