Sir Thomas inherited the vast property holdings in the counties of Kent and Sussex from his father Sir John. He was the Sheriff of county Kent during the time of King Edward I, who ruled from 1272 to 1307. He had four sons, all vigorous men of arms. All four sons, Sir Thomas, Walter, John and Nicholas, were involved with Lord Thomas, Earl of Lancaster, in his rebellion against King Edward II in 1321. Sir Thomas, the oldest, from whom all the American Culpepers descend, inherited Bay Hall. Walter, the second son, inherited Preston Hall. John and Nicholas were given estates by their father, Sir Thomas.