Maio di Monopoli, also known as Matteo or Madio, who is often mistakenly attributed the surname Orsini, probably began his career as a pirate.
Born in Monopoli, from where he was forced to flee with some companions for having killed a person of high rank. He found refuge on the island of Cephalonia, and conquered it, later he also managed to conquer the islands of Corfu, Zante and Ithaca becoming their count.
He managed to significantly strengthen his power, skillfully balancing his political and strategic position between East and West, without breaking the feudal bond with the Latin Empire, which had become only nominal after the defeat in 1217 of Pierre de Courtenay who had been taken prisoner by Theodore Angelos (a strongman of Epirus), submitting to the protection of the papacy, and finally drawing closer to Theodore Angelos Ducas himself, who had been emperor of Thessalonica since 1225, sebastocrator, and nephew of the Byzantine emperor Isaac II Angelos, until he married his daughter Anna Angelos in 1226.
The defeat and capture of Theodore Angelos in the battle of Klokontiča, on 9 March 1230, did not find him unprepared, Mayo quickly changed the pattern of his alliances, seeking support in the principality of Achaea, probably in 1236. Two meetings between Frederick II and Mayo of Monopoli are documented, the first on 3 July 1228, when the emperor's fleet landed in Argostoli on the occasion of the departure for the crusade, the second in 1229, when Mayo met the emperor again in Melfi as nuntius of the Ducas.
The date of death is unknown, certainly after January 1238.
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