He enlisted in Gridley's Regiment of Massachusetts Artillery on July 7, 1775 as a lieutenant, and later that year was promoted to captain lieutenant of Knox's Regiment, Continental Artillery, on December 10.
He was with his guns at the siege of Boston, as well as the battles of Long Island, White Plains, Trenton, Brandywine, Germantown, and Monmouth.
He was promoted to captain in the 3rd Continental Artillery on January 1, 1777, and brevetted major on August 25, 1783.

In 1786, he helped to survey the Seven Ranges, the first lands laid out under the Land Ordinance of 1785.
With inside knowledge of the area, he went on to form the Ohio Company of Associates, was an important shareholder in the Scioto Company, and as of 1787, secretary of the Ohio Company.

Sargent was appointed by the Congress of the Confederation as the first Secretary of the Northwest Territory, a post second in importance only to the governor, Arthur St. Clair.
He took up his post in 1788.
 Like St. Clair, Sargent would function in both civil and military capacities; he served as acting Adjutant General of U.S. Army from September 1791 until he was wounded twice at the Battle of the Wabash, on November 4, 1791.
  On August 15, 1796, he would, as Acting Governor, proclaim the establishment of Wayne County, the first American government in what is now Michigan.

President John Adams then appointed Sargent the first Governor of the Mississippi Territory, effective from May 7, 1798 to May 25, 1801.
 His last entry as Northwest Territory's secretary was on May 31, 1798; he arrived at Natchez on August 6, but due to illness was unable to assume his post until August 16.

The subject was a cotton planter, marketing his crop in New York by Gilbert and John Aspinwall, merchants.
He enlisted in Gridley's Regiment of Massachusetts Artillery on July 7, 1775 as a lieutenant, and later that year was promoted to captain lieutenant of Knox's Regiment, Continental Artillery, on December 10. He was with his guns at the siege of Boston, as well as the battles of Long Island, White Plains, Trenton, Brandywine, Germantown, and Monmouth. He was promoted to captain in the 3rd Continental Artillery on January 1, 1777, and brevetted major on August 25, 1783.
In 1786, he helped to survey the Seven Ranges, the first lands laid out under the Land Ordinance of 1785. With inside knowledge of the area, he went on to form the Ohio Company of Associates, was an important shareholder in the Scioto Company, and as of 1787, secretary of the Ohio Company.
Sargent was appointed by the Congress of the Confederation as the first Secretary of the Northwest Territory, a post second in importance only to the governor, Arthur St. Clair. He took up his post in 1788.  Like St. Clair, Sargent would function in both civil and military capacities; he served as acting Adjutant General of U.S. Army from September 1791 until he was wounded twice at the Battle of the Wabash, on November 4, 1791.   On August 15, 1796, he would, as Acting Governor, proclaim the establishment of Wayne County, the first American government in what is now Michigan.
President John Adams then appointed Sargent the first Governor of the Mississippi Territory, effective from May 7, 1798 to May 25, 1801.  His last entry as Northwest Territory's secretary was on May 31, 1798; he arrived at Natchez on August 6, but due to illness was unable to assume his post until August 16.
The subject was a cotton planter, marketing his crop in New York by Gilbert and John Aspinwall, merchants.
Winthrop Sargent