Skyloyiannis - the nickname means "dog-John" in Greek - was born in 1726. He was a member of the famous Mavromichalis clan that later contributed Petrobey Mavromichalis and others to the Greek War of Independence.
When the Russians, under Aleksey Grigoryevich Orlov, arrived in Mani on February 28, 1770, touching off the events known in history as the "Orlov Revolt", Skyloyiannis took part leading 400 men in the siege of Methoni and Koroni in SW Peloponnesus.
When Haji-Osman Pasha arrived, with an army of 8,000 men, in Peloponnesus to quell the revolt, Skyloyiannis was forced to lift the siege and retreat towards Mani. He held off the superior Turkish forces for several days but many of his men started to desert him as the situation grew hopeless. He retired with his sons and 24 men who remained loyal to him, at Melipyrgos, Messenia. The Turks besieged him and, after a valiant resistance of two days and nights, Skyloyiannis and his men charged out of their fort which had been set ablaze on April 4, 1770. They fell to the last man.