Dejan Dragaš was a 14th-century Serbian nobleman and the Despot

Despot

Despot may refer to:* Despot , a Byzantine court title* Despotism, a form of government in which power is concentrated in the hands of an individual or a small groupPeople with the surname Despot:...

 of Kumanovo

Kumanovo

Kumanovo is a city in the Republic of Macedonia and is the seat of Kumanovo Municipality which is the largest municipality in the country. Municipal institutions include a city council, mayor and other administrative bodies.-Name:...

 holding the title of Sebastokrator

Sebastokrator

Sebastokratōr was a senior court title in the late Byzantine Empire. It was also used by other rulers whose states bordered the Empire or were within its sphere of influence. The word is a compound of "sebastos" Sebastokratōr was a senior court title in the late Byzantine Empire. It was also used...

 given to him by his brother-in-law Emperor of Serbia

Serbian Empire

The Serbian Empire was a short-lived medieval empire in the Balkans that emerged from the Serbian Kingdom. Stephen Uroš IV Dušan was crowned Emperor of Serbs and Greeks on 16 April, 1346, a title signifying a successorship to the Eastern Roman Empire...

 Dušan the Mighty (Dejan married Theodora Eudokia, sister of Dušan)

The Dragaš family were supporters of the House of Mrnjavčević

House of Mrnjavcevic

The House of Mrnjavčević was a medieval Serbian noble house that existed during the Serbian Empire, its fall, and the subsequent years when it held a region of present-day Macedonia region. The house ruled a province from its base at Prilep from 1366 to 1395.Vukašin Mrnjavčević was a military...

 and built up strongholds in several Serbian cities during the rule of Vukašin Mrnjavčević

Vukašin Mrnjavcevic

Vukašin Mrnjavčević was a Serbian ruler in modern-day central and northwestern Macedonia, who ruled from 1365 to 1371. According to 17th-century Ragusan historian Mavro Orbin, his father was a minor noble named Mrnjava from Zachlumia, whose sons Vukašin and Uglješa were born in Livno in western...

, such as Velbužd and Kumanovo

Kumanovo

Kumanovo is a city in the Republic of Macedonia and is the seat of Kumanovo Municipality which is the largest municipality in the country. Municipal institutions include a city council, mayor and other administrative bodies.-Name:...

, including former land of Jovan Oliver

Jovan Oliver

Jovan Oliver Grčinić, known as Despot Jovan Oliver was a magnate of the Serbian Emperor Dušan the Mighty , holding the titles of sebastokrator and despotes, and the great voivode-military rank, showing his prominence and status as one of the most important nobles of Dušan...

.

He had two sons and one daughter with his wife Theodora Eudokia:

• Constantine Dragaš
  Constantine Dragas
  Constantine Dragaš Dejanović was a Serbian magnate that ruled the area around Kyustendil from 1378, during the fall of the Serbian Empire, until his death on May 17, 1395 at the battle of Rovine...
  
  
• Jovan Dragaš
  Jovan Dragaš
  Jovan Dragaš was a 14th-century Serbian noble that held the title of Despot of Kumanovo, Kocani and Strumica under his uncle Stephen Uroš V of Serbia; he later became an Ottoman vassal after the Battle of Maritsa in 1371....
  
  
• Teodora Dragaš