Castilian Civil War
In 1366 the Castilian Civil War began when Henry of Trastámara, natural son of King Alfonso XI of Castile, fought his older half brother Peter of Castile to usurp the throne. After being crowned at Burgos, Henry made his way to Toledo. Padilla came over to Henry's side at this time. After the Battle of Nájera (3 April 1367), Peter sent him as a prisoner to Alcalá de Guadaíra Castle near Seville, where he died in 1368.