Joan I died in 1353 and the Kingdom of Naples including B. was contended by the Duratians, the Aragoneses and the Angevins; at the end of the century Raimondo Del Balzo Orsini, prince of Taranto, took advantage of the political instability and became Lord of B.
In 1442 the king Alfonso I of Aragon conquered the Kingdom of Naples and allowed the prince of Taranto, Giovanni Antonio Del Balzo Orsini to rule the town reduced to extreme weakness by the plague and the civil fights. Ferdinand I, descendant of Alfonso I, deposed the prince Orsini and granted the town many privileges.
In 1496 the Venetians were temporarily offered to rule Brindisi which they considered to be a lucky yet short parenthesis. During their rule (13 years) they improved their defences and supported commerce.