The marriage resulted in Constantine's wealth and status increasing, and also paved the way for his tenure as regent of Montferrat, on behalf of Boniface's young son William IX, from 1495 to 1499.

In the early 16th century, Constantine served as a diplomat to the popes and the future Holy Roman Emperor Maximilian I, with both parties finding him to be a talented ambassador.

Following his assumption of the titles 'Prince of Macedonia' and 'Duke of Achaea', to which he had no real claim, in the 1490s, Constantine partook in various schemes to organize expeditions against the Ottoman Empire, being involved in at least three separate crusade-related plans throughout his life.

Despite his tenuous association with these titles, Constantine adamantly defended his use of them and, as seen through the roles he was expected to play in the various schemes he engaged in, was ready to risk his life to enforce his claims.

Instead, papal taxation policies made Constantine, as the governmental representative, disliked, and contemporary writings mock his insistence on his high-sounding titles.

He was removed from office by Leo in 1516, following a riot by the locals, but was reinstated by Pope Clement VII in 1524, whereafter Constantine governed Fano from a mountain fortress at Montefiore Conca until his death in 1530.

After the death of both Skanderbeg and Gjergj in 1468, the Ottomans slowly managed to crush the Albanian resistance, successfully having incorporate the country into their empire by 1479.

During the long and drawn-out process of Ottoman conquest, many of the Albanians who chose to remain Christian fled across the Adriatic Sea to Italy.

In 1499, Louis XII of France deposed Constantine during the Second Italian War, on account of "lukewarmness in the French cause", and had him imprisoned in the city of Novara.

Constantine's diplomatic ability impressed Julius to such an extent that his monthly pension was increased to 200 ducats and he was put in charge of his own detachment of papal soldiers.

[11] The negotiations in which Constantine was involved eventually resulted in the formation of the unsuccessful League of Cambrai in 1508, an alliance to counteract the Ottomans and the Republic of Venice.

[12] According to the historian Jonathan Harris, Constantine's involvements in these affairs illustrates his willingness to make good on his claims in Greece and aspire to his father's role of anti-Ottoman leadership.

It is unclear when exactly Constantine began to claim this title, though it may have begun only a few months after Andreas's death given that a letter from Antonio Giustiniani, Venetian ambassador to the Pope, mentions a 'despot' in command of a cavalry unit in October 1502.

[13][1] The March of Ancone was a strip of territory facing the Dalmatian coast across the Adriatic Sea, making it a natural launching point for an invasion of the Ottoman Empire's lands in the Balkans.

In September 1513, Leo had issued crusade indulgences for the first time in many years and the pope had concentrated efforts on promoting unity among the monarchs of Europe.

Through using the architectural styles of their homelands and retaining traditions and customs, the refugees and their descendants in Ancona continued to foster links with their pasts.

Though Constantine would ultimately not succeed in gaining control of the regions he claimed to be the rightful ruler of, he may have aspired to be accepted by the Balkan refugees in Fano and the rest of the March of Ancona as a leadership figure.

[19] Constantine was not popular among the people of Fano, being disliked not only by the Italians but also by the Albanians and Greeks, who were mostly discontent over the heavy taxations by the Papacy owing to the recent wars in Italy.

In the comedy La Cortigiana by the contemporary author, playwright, satirist and poet Pietro Aretino, Constantine's titles are explicitly mocked in the text.