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Leonard Helm was born around 1720 probably in Stafford County, Virginia. He died while fighting Native American allies of British troops during one of the last engagements of the Revolutionary War around June 4, 1782 in Jefferson County, Virginia (now Kentucky).

Helm was commissioned a captain and asked to raise and lead a company of Virginians by the newly promoted Lieutenant Colonel George Rogers Clark. On January 2, 1778, Governor Patrick Henry gave Clark the authority to raise a regiment and secret orders to attack British forces and their allies on Virginia's frontier. Leonard Helm, who had served with Clark during the French and Indian War and had spent a lot of time in Kentucky, was given command of one of the initial four companies created to form this regiment. Captain Helm recruited soldiers from the Virginia militia from both Prince William and Fauquier Counties. Clark's unit was later known as the Illinois Regiment and participated in the Northwest Campaign. Clark and his men captured Kaskaskia, Illinois on July 4, 1778 and Cahokia, Illinois July 6, 1778. During the capture of Kaskaskia, Clark split his force, commanding one half himself with Captain Helm commanding the other. The Illinois Regiment followed up their success with an attack on Fort Sackville (in present day Vincennes, Indiana) which surrendered on February 25, 1779. Captain Helm was put in command of Fort Sackville (renamed Fort Patrick Henry) with a group of local French speaking militiamen and four soldiers from Virginia.

The British later retook the fort after Helm's local militia had deserted and he had too few men to attempt resistance. Knowing that the British did not fully understand his tactical situation he demanded and received favorable terms of surrender. Lieutenant Colonel Hamilton was later shocked to find only three people within the fort but honored his agreement. When Clark heard about the surrender several months later, he and his force made a bold march through icy winter weather and recaptured Fort Patrick Henry. Clark later appointed Captain Helm as the Superintendent of Indian Affairs and commander of the fort in present day Louisville, Kentucky. Captain Helm was killed while serving as the commander of this fort. Many years later his heirs received 4,666 acres (19 km²) of land from Virginia for his service in the Illinois Regiment.