Syrgiannes Palaiologos

Loyal only to himself and his own ambitions, he switched sides several times, and ended up conquering much of Macedonia for the Serbian ruler Stefan Dušan (r. 1331–1346) before being assassinated by the Byzantines.

He was named after his father or possibly grandfather, a Cuman leader who became megas domestikos (commander-in-chief of the Byzantine army) under Emperor Andronikos II.

Although initially popular with his grandfather, the younger Andronikos and his entourage of young nobles, to which Syrgiannes belonged, had by that time caused the elder emperor's displeasure by their extravagance.

Their excesses culminated in the mistaken-identity murder of the young emperor's younger brother, Manuel; enraged, the elder Andronikos annulled his grandson's titles, and a deep personal rift was opened between the two.

[6] At that time, Syrgiannes and John Kantakouzenos bought for themselves governorships in Thrace, where discontent with the old emperor was rife, and they quickly mobilized support for the younger Andronikos.

Syrgiannes was freed, and was able to restore himself to Andronikos's favour, to the extent that in late 1329 he was entrusted with the important governorship of Thessalonica, the Empire's second-largest city, and of western Macedonia and Albania.

[11][20][21] With the loss of their principal military leader, the Serbs settled for a negotiated peace with the Byzantines, which was very advantageous for them as they were left in possession of most of the cities won by Syrgiannes in northern Macedonia.

[22] Syrgiannes's ambition, inveterate plotting, and multiple betrayals made him one of the darkest figures of the era in the eyes of both contemporary and later historians: the 14th-century historian Nikephoros Gregoras compared his flight to Serbia with Themistocles's flight to the Persians, while Donald Nicol likened him to Alcibiades and Angeliki Laiou called him "the most evil presence" of the civil war.