Charles I of Anjou vs John I of Portugal

Charles I of Anjou defeated Manfred of Hohenstaufen at the Battle of Benevento, conquering the Kingdom of Sicily. He was crowned king in Rome with papal support, establishing Angevin rule in southern Italy.

Charles I defeated Conradin of Hohenstaufen at the Battle of Tagliacozzo, ending Hohenstaufen claims to Sicily. Conradin was captured and later executed, solidifying Angevin control and earning Charles a reputation for ruthlessness.

Charles I negotiated with the Pope and other powers to launch a crusade against the Byzantine Empire, aiming to restore the Latin Empire. He used Sicily as a base for naval preparations, but the plan was delayed by the Eighth Crusade.

A popular uprising in Palermo, known as the Sicilian Vespers, expelled Angevin rule from Sicily. The revolt was supported by Peter III of Aragon, leading to a war that cost Charles control of the island and weakened his power.

Charles I died at Foggia, leaving his son Charles II a reduced kingdom. The loss of Sicily and the ongoing war with Aragon ended his dreams of a Mediterranean empire, and the Angevin dynasty never recovered its former power.

John I led Portuguese forces to a decisive victory over the Castilian army at Aljubarrota. This battle secured Portuguese independence and solidified John's claim to the throne.

John I became King of Portugal after the 1383-1385 Crisis, being elected by the Cortes of Coimbra. His accession ended the Burgundian dynasty and founded the House of Aviz.

John I signed the Treaty of Windsor with England, establishing a perpetual alliance between Portugal and England. This alliance, the oldest in the world, has endured to the present day.

John I led the conquest of Ceuta in North Africa, marking the beginning of Portuguese overseas expansion. The capture of the city opened the era of European colonialism.