A Master of Alcántara was killed in the Battle of Atoleiros (1384), to the consternation of Juan I of Castile and his faction who wish to avenge his death, as stated by Fernão Lopes in chapters 145 and 146 of the Chronicle of King João I of Portugal, Part I. Lopes does not mention any names, but the dead Master is probably Diego Gómez Barroso (1383-1384) and his replacement is Gonzalo Núñez de Gusmán (1384-1385).
See: Ordem de Alcántara and check the names of the various Grand-Masters.
Religious Military Order established by Alfonso VIII of León and Castile in Uclés and approved by Pope Alexander III in 1174. Because of the location of original headquarters, it was often known as the Order of Uclés.
The Order of Santiago was a decisive factor in the wars against the Moors during the period of the Reconquest. When that role became less relevant they became involved in Castilian internal strife for power, becoming a lynchpin of the power of Castilian monarchs.