Anthony Bennett was one of the older sons of Joseph Bennett Sr. and grew up on a tobacco plantation in southern Virginia, not far from the present day town of La Crosse.
From "Mecklenburg County marriages, 1765-1810", Anthony Bennett married Susannah Davis on December 13, 1779, with surety John Brown.
In 1787 Anthony served as surety at the wedding of Joseph Bennett to Elizabeth Burrus.
In Mecklenburg County deed books, Anthony sold substantial property to his father, Joseph Sr., in 1796.
Sometime between 1796 and 1800 Anthony and Susannah joined the tide of pioneers flowing through the Cumberland Gap, settling in Henderson County, Kentucky.
In 1800 Anthony Bennett served as the executor of a will in Henderson County, Kentucky.
Unfortunately, Anthony's life came to an end shortly after they arrived.
In the February 1805 will of his father, Joseph Bennett Sr., Anthony is mentioned; " to the representatives of my son Anthony, late of the state of Kentucky, deceased.".
His date of death is estimated, based on his last known activity in 1800 and his father's will of 1805.