Brigadier General James Winchester was born on February 6, 1752 in Carroll County, Maryland. His father, William Winchester, a surveyor, trained his son in his profession. The young James Winchester became well known and widely respected for his work in the field before the Revolution.

In 1776, James Winchester enlisted as a private in the Continental Army. He served to the end of the war, rising to the rank of Captain and leading in the organization of the Society of Cincinnati.

After the Revolution, Winchester and his brother George bought land in the Cumberland settlements in what is now Sumner County, Tennessee, where both men became active in the frontier military and government. George was killed by the Chickasaw in 1794, but James prospered, establishing trade in tobacco and other goods with merchants in New Orleans and a number of other cities. In 1802, he built a large residence, named "Cragfont," which a contemporary described as "the most elegant house west of the Appalachians." (ANB vol. 23 p. 625) He married Susan Black, with whom he already had four children, in the following year. He also remained active both in the government and in the military, becoming brigadier general of the militia and speaker of the senate when Tennessee became a state.

During the first ten years of Tennessee's statehood, Winchester expanded his landholdings and his commercial concerns. He also agitated politically for territorial expansion, supporting the "War Hawks" who wished to annex Spanish Florida and parts of Canada. When Congress declared war on Great Britain in June of 1812, Winchester, who had already been appointed Brigadier General of the U. S. Army, took charge of recruitment in the Ohio and Mississippi valleys. In August, shocked by the news of the fall of Detroit, Winchester assumed command of the Left Wing of the Army of the Northwest under General William Henry Harrison. Accompanied by his son Marcus, who served as his aide, Winchester marched towards the Michigan territory. His troops won several skirmishes en route, but were overwhelmed and defeated near Frenchtown. Winchester, his son, and many others under his command were imprisoned and held at Quebec for over a year. In April 1814, Winchester was exchanged and returned home, where he received a hero's welcome despite his defeat. He took command of the Eastern Section of the Seventh Military District at Mobile a few months later, where he served under the command of Andrew Jackson until March 1815. After resigning his commission, he returned home to Cragfont, where he engaged in commercial enterprises and wrote extensive justifications of his defeat at Frenchtown.

In 1818, together with Andrew Jackson and John Overton, he planned a new city on the Mississippi river. Winchester named the city Memphis, in hopes that it would become to the new society what the ancient city of Memphis had been to the Egyptians. Winchester's son Marcus became the city's first Mayor when it was incorporated, shortly before James Winchester's death at Cragfont on July 26, 1826.