He is best remembered for leading the opposition to the State of Franklin movement in the 1780s, as well as for his rivalry with Franklinite leader John Sevier.

[2] Tipton married Mary Butler in 1751, and they had nine sons: Samuel, Benjamin, Abraham, William, Isaac, Jacob, John, Thomas and Jonathan.

[2] By the late 1750s, Tipton as a young man owned a 181-acre (73 ha) farm along the Shenandoah River in Frederick County, where he raised crops and livestock, and produced whiskey.

In June 1774, Tipton was elected to the county's Committee of Safety and helped craft the Woodstock Resolutions, which denounced the British Crown's actions in closing the port of Boston.

[3] During Dunmore's War later that year, Tipton served as a captain under Andrew Lewis and saw action at the Battle of Point Pleasant in October.

[2] In the 1770s, Tipton's brothers Jonathan and Joseph, along with their aging father, moved to the Tennessee frontier, which at the time was controlled by a fledgling government known as the Watauga Association.

[2] In June 1784, North Carolina ceded its lands west of the Appalachian Mountains (i.e., modern Tennessee) to the Continental Congress.

The Franklinites and loyalists (the latter sometimes called "Tiptonites") set up parallel governments that gradually grew hostile to one another.

Two days after the siege began, a Sullivan County militia loyal to North Carolina arrived on the scene and scattered Sevier's forces.

In October, Sevier was involved in a melee in Jonesborough, and Tipton was notified that he was staying in the home of Mrs. Jacob Brown.

Mrs. Jacob Brown sat down in the doorway to prevent Tipton from entering, while Sevier stepped out through a side door and surrendered to a more amiable loyalist, Colonel Robert Love.

[6] In November 1789, North Carolina ratified the U.S. Constitution and passed a second cession act in December, ceding its trans-Appalachian lands to the new U.S. government.

[8] In 1794, Tipton was elected to the territorial legislature, where he served on the Committee for Petitions and Grievances alongside James White and William Cocke.

[2] In 1795 and 1796, French botanist André Michaux stayed with Tipton while on a trip to study new plant species on the Appalachian frontier.

[12] In the early 19th century, Tipton's son, William (1761–1849), known as "Fighting Billy," acquired much of the land in Cades Cove, in the Great Smoky Mountains.

Tipton's farm, the Tipton-Haynes Place in Johnson City, is now designated as a state historic site.

[2] For years after Tipton's death, the leader was criticized by historians, most of whom held favorable views of his rival, Sevier.