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Benjamin Cleaveland was born in Prince William County on May 26, 1783 in Virginia. In 1769 Cleaveland moved to North Carolina to modern day Wilkes County. During the Revolutionary War Benjamin Cleaveland gained the reputation for harsh treatments to Loyalists. Benjamin Cleaveland participated in the defeat of the British at Kings Mountain which is later known as the "turning point of the war in the south" Cleveland County formerly spelled Cleaveland County would be named after Benjamin Cleaveland.

As a child Benjamin Cleaveland grew up in Orange County, Virginia and learned to hunt, fish, trap, farm, and carpentry. Benjamin Cleaveland would take his talents and put them to use in Wilkes County, North Carolina. This man of many talents would become the wealthiest man in the county by the American Revolution. At the beginning of the war Cleaveland would be commissioned to be a colonel in the North Carolina militia. As a colonel, Benjamin Cleaveland became known as the "Terror of the Tories" for his treatment of those loyal to the crown. The legend of Benjamin Cleaveland would grow at the Battle of Kings Mountain. The Battle of Kings Mountain featured an army of Tories led by Major Patrick Ferguson and an army of Patriots. Benjamin Cleaveland bravely led his men into battle, contributing to a key Patriot victory. After the Patriot victory and Major Ferguson's death, it is said that Benjamin Cleaveland rode off on Ferguson's white stallion as a war prize. After the war Benjamin Cleaveland would leave the state of North Carolina and go southward to South Carolina. While at his home in Oconee County, South Carolina, Benjamin Cleaveland would die due to heart dropsy or also known as Edema. Benjamin Cleaveland would leave behind a legacy as a Revolutionary War and a state legislator. Cleaveland County, North Carolina would change the spelling of its name to Cleveland in honor of President Grover Cleveland in 1887. This spelling change has led to the misspelling of Benjamin Cleaveland that is often times seen today.
William S. Powell, North Carolina Through Four Centuries, (Chapel Hill: The University of North Carolina Press), 199.