The Siege of Negroponte was fought between the forces of the Ottoman Empire, led by Sultan Mehmed II in person, and the garrison of the Venetian colony of Negroponte (Chalcis), the capital of the Venetian possession of Euboea in Central Greece. It lasted for almost a month, and despite great Ottoman casualties ended in the capture of the city and the island of Euboea by the Ottomans.
The leader of the Venetian relief force was Nicolò Canal, known as "a man of letters rather than a fighter, a learned man readier to read books than direct the affairs of the sea." His fleet had 53 galleys and 18 smaller ships, a fifth of the Ottoman fleet's size. He arrived three weeks into the siege, lost his nerve and withdrew to Samothrace, asking for more help, but only Papal indulgences arrived. Canal could have broken the siege if he had attacked the Pontoon bridge the Turks depended on. Wind and tide were in his favour and the Venetians were sailing 15 knots towards it, but he lost his nerve and withdrew. He took his now mutinous fleet back to Venice and Negropont surrendered the next day.
Upon entering the city, the Turks committed massacres against the inhabitants. The men were slaughtered, Christian boys were kidnapped and raised as Islamic janissaries, women were taken as harems, Greek citizens were enslaved and Italian soldiers were flayed alive and impaled on wooden stakes. More than 6,000 Italians and Greeks died in defense of Negroponte. Only 30 known survivors made it back to Venice, consisting of 15 women, 12 children, 3 men. The garrison commander, bailoPaolo Erizzo, was sawed in half. Canal was tried, fined, stripped of his rank and exiled to Portogruaro.