He lived 80 years during the reigns of  Edward IV and V, Richard III, and Henry VII and VIII and was witness to the great turmoils of those strife ridden times of the Wars of Roses and the intrigues of the Tudor era. His father, Sir William Cary of Cockington was in the Battle of Tewkesbury on the Lancastrian side and beheaded after it, so some involvement at Bosworth Field may be expected. 

His father's property was confiscated as is usual in such cases, but Henry VII restored it to his son Robert.  We cannot ascertain for what reason,  but probably because King Henry was a scion of the House of Lancaster in whose cause, his  father lost his life and property.