Hajduk Momcilo
Unknown — 1345 The flip-flopping Momčilo always followed the money
Hajduk Momčilo, known as Momchil, began his criminal career as a bandit terrorising the Rhodope Mountains. Assisted by his peasant army, he struck fear into the hearts of travellers.
Because the territory he prowled was part of an ongoing border dispute, the warring parties of Serbia, Bulgaria and the Byzantine Empire all wanted to secure Momčilo’s support. He was ennobled and his outlaw army became a recognised military force.
When the Byzantine Civil War broke out in 1341, Momčilo played both sides off against each other like a pro. By switching between Stephen Dušan and his opponent, Emperor John VI Cantacuzene, on multiple occasions, when he left Cantacuzene’s service to throw his considerable might behind Dušan once too often, his card was marked.
Cantacuzene declared him an enemy and Momčilo was killed at Peritheorion, when the townspeople locked the city gates and left him to the mercy of his enemies.