Possibly the most famous of three related men of the same name who served in the Virginia legislature during the 18th century, and despite genealogical disagreement this man was most likely the son of Dudley Digges of Yorktown and Williamsburg and his first wife, Martha Burwell Armistead.

He served during the American Revolutionary War as a dragoon in the Continental Army, rising from the rank of cornet to lieutenant before resigning and starting his legislative career.

[1][2][3] The other two related men of the same name were his grandfather, Yorktown merchant Cole Digges who served in both houses of the Virginia legislature, and his cousin Cole Digges (d. 1777) who briefly represented Warwick County in the House of Delegates before his death and this man's succession.

This Cole indirectly succeeded to the seat in the Virginia House of Delegates representing Warwick County vacated by the death of his cousin of the same name, although neighbor Edward Harwood actually won the election for that seat, and served alongside this man several additional times.

By the 1787 tax census, he owned 33 adult slaves and 35 enslaved teenagers in Warwick County as well as 21 horses, 94 cattle and also owned a riding chaise, and 10 adult slaves, 5 enslaves teenagers, 5 horsed and 40 cattle in James City County.