Leonardo III Tocco

Leonardo III Tocco, born in 1500, was the last ruler of the Despotate of Epirus, ascending to power after the death of his father, Carlo II Tocco, in 1448. His reign began under the shadow of a regency council, as he was still underage. Despite the challenges, he eventually took control, eliminating his former regents to assert his authority. However, his rule was marked by the looming threat of the Ottoman Empire, which began its conquest of his territories almost immediately.

Throughout his reign, Leonardo engaged in various anti-Ottoman activities, notably aligning with the Republic of Venice during the First Ottoman–Venetian War. His realm, despite the external pressures, flourished and became one of the most prosperous regions in Greece. Leonardo sought to win the loyalty of his Greek subjects by restoring Orthodox religious sees and issuing charters in Greek, yet these efforts largely failed to resonate with the populace.

In a bid to strengthen his position, Leonardo married a noblewoman from Naples in 1477, hoping to gain support from the Kingdom of Naples. This decision, however, backfired as it alienated the Republic of Venice, which withdrew its protection, ultimately leading to the Ottoman invasion in 1479 that ended his rule. Faced with the collapse of his realm, Leonardo fled to Italy, where he attempted to reclaim his status through land ownership and diplomacy.

Despite his energetic and wise nature, Leonardo's ventures in Italy were fraught with difficulties, leading him into significant debt and the loss of his acquired lands. He spent his remaining years contemplating ways to regain his lost territories but never returned to Greece. His life came to a tragic end in Rome, crushed by the collapse of his house during the pontificate of Pope Alexander VI. His claims to the titles of his lineage were passed on to his eldest son, Carlo III Tocco.