He was a younger son of Ladrón de Guevara, Lord of
Escalante near
Santander in northern Spain, and his date of birth is unknown, but may have been as early as "about 1450". After his death the
Constable of Castile wrote to
Charles V praising Guevara's more than forty years of service to the Dukes of Burgundy. He may have been at the Burgundian court as a page or
valet de chambre from a relatively young age, and an early 16th-century source says he spent
toute jeunesse ("all [his] youth") at the court. His older brother, another Ladrón de Guevara, had been in the Burgundian court long before him, before 1461 according to a 16th-century history of the family. This also said that Diego was an esquire of the Valois Duke
Charles the Bold at the disastrous
Battle of Nancy in 1477, and threw himself over Charles' dead body to protect it. He is recorded as an esquire of Charles's daughter and successor
Mary of Burgundy at the time of her death in 1482, and continued in the service of her son
Philip the Handsome, Duke of Burgundy. with Guevara's portrait He rose through the ranks of the ducal household, becoming
chamberlain by 1501. He was first ''maitre d'hotel'' to Philip's wife, Queen
Joanna of Castile (Joanna the Mad) when the couple travelled to Spain in 1506. Charles appointed him knight and warden (
clavaría) of the
Order of Calatrava in 1517, and in 1518
Mayordomo mayor, an important role in charge of his personal apartments and arrangements. Diego de Guevara died in
Brussels on 15 December 1520. He was a cousin of
Antonio de Guevara, and had at least one child, his illegitimate son
Felipe (see below). It is possible that his female relatives lived in the Netherlands with him. A portrait by the
Master of the Legend of the Magdalen, shows a lady in a Netherlandish outfit, described as Marguerite (de) Guevara, lady in waiting to
Eleanor of Austria. ==Art collector==