Don Diego de Guevara (c. 1450–1520) was a Spanish courtier and ambassador who served four, possibly five, successive Dukes of Burgundy, spanning the Valois and Habsburg dynasties, mostly in the Low Countries. He was also a significant art collector.
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.
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. He was used as an ambassador, then usually an appointment for a relatively brief mission, to England and the court of Ferdinand II of Aragon. After Philip’s death in 1506, Diego became councillor and chamberlain to Philip’s son Charles V, Holy Roman Emperor. 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.