A HISTORY OF MACEDONIA IN THE MIDDLE AGES
This article is an attempt to present the history of the geographical region of Macedonia in more trustworthy and more impartial way on the base of authentical documentary material.
From historical point of view Bulgarian ethnical presence in Macedonia is as old as it is in all the other Bulgarian regions, most of which like Macedonia are not within the boundaries of today's Bulgarian state. So it s not without reason to ask why today's Bulgaria includes the smallest Northeastern part of Macedonia. Is this a consequence of the political mistakes only done during the past twentieth century or is it a result of an all-round policy started by the Bulgarian statesmen as far back as Middle Ages? Where actually was the strongest Bulgarian ethnical presence in Macedonia and did it coincide with the Bulgarian state-political presence there during the Middle Ages? Why, however, Macedonia was and still is an apple of discord for all Balkan nations (Bulgarian, Serbian, Greek, Albanian, Turkish and Rumanian)?
In order to give more objective and well-grounded reply to all these questions we have to remember some basic moments of Macedonian ancient history. By the beginning of the 6th century BC the ancient Hellenistic (Hellenic like, Greek like) state of Macedonia took shape on the territory of today's geographical region. Ethnically the ancient Macedonians were related to the ancient Greeks, Thracians and Illyrians. Their state gained strength under the rule of King Philip II (359-336 BC), who created the famous Macedonian phalanx which helped him to conquer most of Greece and Thrace.
His son Alexander III the Great (336-323 BC) made of Macedonia one of the earliest large empires in human's history. He took hold of all the Near East and part of the Middle East as far as India. After his death however this empire and even the old Macedonian kingdom fell apart into separate Hellenistic states led by Alexander's commanders, descended from distinguished aristocratic families. They started long and bloody civil wars, which weakened even more the ancient Macedonian state. In addition, most of the native Macedonian population gradually moved east and their lands were occupied mainly by Greek mercenaries, Hellenized Thracians and Illyrians, as well as Celts. This fact quickened the processes of Hellenization. On the other hand, the weakening Macedonian state because of its strategic situation gradually became one of the first targets of rising Rome. In 168 BC, after three heavy wars, the Romans finally conquered Macedonia and divided it into four separate parts. In other words Macedonia became one of the first Balkan countries, conquered by Rome and thus one of the first regions on the peninsula submitted to the processes of Romanization. Roman authority led purposeful policy in this respect conducting constant administrative changes and moving great masses of Italian and Anatolian population.
But the ethnical aspect of the Balkans started changing radically in the middle of the third century AD when the peninsula was exposed to barbarian invasions. These affected Macedonia as well. It can be firmly stated that as early as the fourth century AD the native population of the region was to a great extent replaced by compact masses of Goths. Probably part of them were Byzantinized within the frame of the East Roman Empire in the 5th century, while the rest of them moved to Italy, Gaul and Spain by the end of the same century. Anyway at the end of Antiquity the old Macedonian ethnic body did not exist anymore - on the territory of Macedonia lived actually some half-barbarous half-Romanized half-Hellenized population, who in order to have more citizen and economic rights strove to define themselves as Romans. The biggest ethnical changes were still to come.
In fact as early as the 5th century the Bulgars as part of Attila's semi-nomadic empire of the Hunns (later on their own) repeatedly crossed the Macedonian land during their raids against the East Roman empire or as its allies. An interesting fact is that according to written sources Bulgarian first more significant penetration in Macedonia took place earlier than that of the Slavs' - as early as the last days of the rule of Emperor Anastasius I, probably in 517, while the Slavs appeared in those lands in the time when on the throne was his successor - Emperor Justin I (518-527).
Notably strong was their pressure during the rule of Justinian I (527-565), when they were in action together with and often under the leadership of the Bulgars. In the second half of the 6th century the Bulgars and Slavs were subject to the Avars, but the barbarian pressure against the empire increased still more. In 586 Avars, Bulgars and Slavs laid the first serious siege to the main Macedonian town Thessalonica and this was the beginning of their age-long ambition to conquer it. In 597 there was another siege. Its failure proved that the invaders' attempts were to be fruitless unless they could keep under control the surrounding area.
In 610 Avars, Bulgars and Slavs launched a mass offensive against Byzantium, which swept the Danubian frontier, destroyed and deVastated important and big fortified towns and laid the beginnings of mass Slavic settlement mostly in Moesia, Dacia and Macedonia. In 615 and 617 they laid two more threatening sieges to Thessalonica and this time the attackers were part of the population located in the vicinity of the city. The Greek sources give us the names of the following Slav tribes on the territory of Macedonia: "Drougouvitai, Sagoudatoi, Berzitoi, Ryghinoi". The ethnical aspect of the region was so radically changed that the name of Macedonia, used to mark the region before disappeared from the evidence for several centuries and another term appeared instead - "Sclavinias". It was only by 675 that the Emperor Constance II managed to find power, ways and means and try to subdue i.e. to put the Sclavinias under tax and political obligation. Due mainly to the lack of co-ordination and low extent of organisation the Slavs in Macedonia were subjected without great efforts though there were some attempts for resistance like that of the Slavic leader Perbound in 675 and two years after his murder the Slavs tried once more to attack Thessalonica.
And right then when it seemed that the empire regained its hold on Macedonia on the political stage there appeared new opponent - more organised, more powerful and for that reason more dangerous - the Bulgars led by Kouber, who tried like their kinsmen subject to Asparoukh to lay the beginnings of another Bulgar state which probably was to be centred round Thessalonica itself. Their attack against the main Macedonian city in about 682-684 failed too but it was much more far-reaching in consequences both political and ethnical for the whole of Macedonia.
First of all it is clear from the evidence that the Byzantine Emperor Constantine IV accepted the existence of another big Bulgar group in Macedonia officially within the boundaries of the Empire but actually under the rule of their own leader Kouber. And what is more he asked the Bulgars to be supplied by the Slav tribe called Drougouvits and that was exactly what was ordered from Constantinople, The Drougouvits themselves neither refused nor protested against this decision. To put it another way the Byzantine emperor acquiesced to concede to the Bulgar chief the right to rule over part of the local Slavs in Macedonia. That was the first success of the Bulgar policy in this respect achieved as far back as the end of 7th century! Constantinople kept on recognizing the Bulgars' special rights in Macedonia even after Kouber's abortive action against Thessalonica which by all means should have been treated by the Empire as disloyalty and rebellion. At that time the Bulgars in Macedonia were called "Sermesianoi" after the name of the region they had come from - Sirmium/Srem (today's Sremska Mitrovica in Serbia). In the long run despite the reverses of fortune it was Kouber's Bulgars that became that oldest Bulgarian main body in Macedonia which laid the beginnings of the Bulgarian national spirit there and determined the long lasted ambition of the Danubian Bulgars to unite all Bulgarians on the Balkan peninsula under one rule. In fact the Byzantines themselves seemed to finally become reconciled with the loss of their old province Macedonia - at the end of the 7th century they established a new administrative district -theme, called again Macedonia but the new one had nothing to do with the ancient province as it included parts of Thrace and the Rodopes while its centre was Adrianople / Odrin (now Edirne). Thus during the following centuries the name „Macedonia" acquired completely different ethnic-political and geographic meaning.
At that time it was already obvious that Kouber's Bulgars would not be able to lay the beginnings of another Bulgar state in Macedonia. That was the reason why their kinsmen round the banks of the Danube started to pursue more active policy aimed at incorporating them into already consolidated Danubian Bulgaria. The first action in that respect dates back to the reign of Khan Telerig about 774. Some nowadays historians in Skopje define this action as „the beginning of the Bulgarian aggression against the Macedonian Slavs". But the analysis of the Byzantine sources shows that even if there was some „Bulgarian aggression" it was not levelled against the local Slavs but against the Byzantine administration in Macedonia.
In fact the Bulgarian military and political penetration in Macedonia began during the reign of Khan Kardam. In 789 one Bulgarian troop penetrated in Struma valley and defeated the main Byzantine camp, which was the first military success worth mentioning.
The first more serious success though took place at the beginning of the 9th century during the reign of Khan Krum. In 808 his armies penetrated again up the Struma valley and next year it was not by chance that he took hold of Serdica (now Sofia), which enabled him to control Northeastern Macedonia.
Probably this attack took place in 812-814 and it gave Khan Krum the chance to recruit auxiliary troops from „all Sclavinias too", i.e. from among the Slavs in Macedonia. His heir Khan Omourtag was probably forced to give part of the newly conquered territories back to Byzantium, but in 837 a Bulgarian army led by Kapkhan Isboul won important victories at Serres and Philipi thus gaining the control over the Western Rodopes and Eastern Macedonia. This was fundamental as it enabled the expansion of the Bulgarian authority towards the central and western Macedonia and the inclusion of the regions along the valleys of Vardar, Drin-Cerna and the Lake of Prespa (the areas around Stip, Skopje, Prilep, Ohrid, Bitola). This process was already finished by the Khan Boris' ascension to the Bulgarian throne in 852. It was during his reign that the territory of the Bulgarian Macedonia was divided into at least three administrative regions - comitats: Bregalnica centred around Skopje, Kutmicevica centred around Devol, later around Ohrid and finally the south-eastern part with its centre Strumica. It was in Kutmicevica that in 886 Boris I sent one of the most distinguished disciples of
Cyril and Methodius - St Clement of Ochrid. His main task there was to create Bulgarian clergy capable of performing the liturgy in Slavic old-Bulgarian language or as it is known Slavonic liturgy. His best disciples formed an entourage of learned men who constituted the so called „Ochrid's Educational Center".
It was there, under the guidance of St Clement and on the orders of Tsar Symeon I at the beginning of the 10th century where a spelling reform was carried out the sense of which was to replace the unintelligible Glagolic alphabet with the so called Cyrillic (actually „Clementic") alphabet.
Most of Macedonia still remained within the boundaries of the First Bulgarian Kingdom during the reign of Symeon's heir Tsar Peter I (927-969). And as an inseparable part of Bulgaria the region shared both its successes and failures, lived in peace and suffered with it the consequences of invasions. In 971 most of the northern Bulgarian territories were conquered by Byzantium and the centre of the Bulgarian state-political life started to move to the south-west of the Balkans where the sons of Nicholas, the Count of Sredec (old Serdica - now Sofia) took hold of the power. Unfortunately this fact is used as grounds for one of the greatest speculations with the history of Medieval Bulgaria. Most of the historians in Skopje announce this fact as the beginning of some „Macedonian Medieval Kingdom". Entering into details is unnecessary as it is quite enough to mention only several things which show that this speculation is absolutely groundless:
until 986 Count Nicholas' sons (Cometopuli) ruled the independant Bulgarian territories in Macedonia and out of it (the regions of Vidin, Branicevo, Belgrade, Nis and Sofia) from Sredec / Sofia which is probably their place of birth. They gave there shelter to the Bulgarian Patriarch. When Tsar Boris II was murdered they welcomed his brother Roman. Roman was castrated so he was not able to be a ruler but nevertheless he was recognized as the legal heir of the throne. Later Roman established his residence in Skopje. Only after his death did Samuel seem to declare himself a Tsar.
Later his nephew John Vladislav stated this clearly in the Inscription of Bitola (kept hidden even today) from 1016 where he is defined himself as "native Bulgarian" and „Bulgarian autocrat". And later on, in 1018, when the Byzantine Emperor Basil II broke down the last efforts of Samuel's successors to resist he called himself „Boulgaroktonos" (Killer of Bulgars) and not „Makedonoktonos" and this is hardly by chance. Basil II divided the conquered lands into several parts. The largest of them included today's Vardar Macedonia it was centred around Skopje and was called by the Byzantines themselves „Thema Boulgaria".
In early Medieval period Bulgarian ethnical and state-political presence is clearly evidenced but later its character became more dramatic and tragic. The Byzantine rule intensified the processes of Hellenization but it could not eliminate the Bulgarian ethnic character of Macedonia and especially of its central, northern and eastern parts. However the Greek ethnic element considerably strengthened its presence in Southern Macedonia.
This fact was first of all felt at the end of the 12 th and the beginning of the 13 th century when the Asen brothers started recovering the system of Bulgarian state in Macedonia. In 1191 the Bulgarians reached for the first time the valley of Upper Struma but could not go farther than Rila Monastery. At the same time the Serbs led by Stefan Nemanja conquered Skopje for the first time and devastated the town and that was an emblematic sign showing the appearence of a third power which was yet to begin challenging the rule over Macedonia.
The Asens started recovering the independence of Macedonia in summer 1195 when a big Bulgarian-Cuman army went up the Struma valley and conquered Melnik and Strumica, i. e. today's Pirin Macedonia was set free first. Next year John I Asen reached ar far as Serres and Amphipolis. But the Bulgarians could not keep those regions and had to withdraw. The Asens appointed a governer for the Struma region. His name was Dobromir Chrysos - Asens' loyal brother-in-arms. For no reason some historians in Skopje today declare that Dobromir Chrysos was „the first independent Macedonian ruler" who threw off the Byzantine dominion. In fact there are explicit historical sources that Chrysos was sprung from the Bulgarian population located to the north of the Balkan mountains and that he supported the Asens' rebellion from the very beginning. Later being the governer of Struma region Chrysos did try to maintain independent political relationship with the Byzantine Emperor Alexius III Angelus (1195-1203). The boyar Ivanko did the same - after he had killed his relative John I Asen and established himself in Plovdiv he was recognized by the Byzantine emperor as a governer of the region. Since then both Chrysos and Ivanko acted either against the Asens or as their allies. I wonder how come noone has yet had the idea to declair Ivanko „the first independent Thracian ruler" or to declair John Spiridanakis - a Byzantine renegade who acted the same way and in the same period in the Rodopes - „the first independent Rodopes ruler"…
In fact Dobromir Chrysos three times backed out of his alliance with the Byzantine emperor under the influence of Tsar Kalojan who acted with great political wisdom turning his back to the desire for personal revenge. At the end of 1202 the Byzantines managed to get rid of Dobromir Chrysos and conquered the Struma region but they could not hold it even for a year. When the crusaders from the Fourth Crusade came to the walls of Constantinople Alexius III hid himself in Debeltos asking desperately Tsar Kalojan for help. But the Bulgarian ruler knew better than that and instead of helping the fugitive in summer 1203 he started conquering Macedonia. He took Skopje, Prizren and Ohrid and appointed a Cuman chief called Cuzmen (Etzuismenos) as a governor of Struma region.
When the crusaders captured Constantinople their leaders started parcelling out the lands of Byzantium. The territory of Macedonia was included within the boundaries of the so called Kingdom of Thessalonica given to marquis Boniface of Montferrat. The result of this and of the consequent military actions was that Thessalonica, Serres and Veria, i.e. the southern and southwestern parts of Macedonia were taken by the Latins, its western parts remained under the rule of the Despotate of Epirus while its northern and northeastern parts remained under the rule of the Second Bulgarian Kingdom. Thus however Macedonia was for the first time divided among more than two political powers.
All this made Tsar Kalojan during the last two years of his reign (1205-1207) constantly trim and wage wars now against the Latins now against the Greeks. Thanks to his extremely clever diplomacy and military tactics this great Bulgarian ruler managed to gain the rule of almost all Macedonian region as it was during the reign of Symeon and as it was later under the rule of Samuel, only that Kalojan could not take Thessalonica. It was under the besieged walls of Thessalonica in September-October 1207 that Kalojan was murdered as a result of a Greek plot. The death of this remarkable statesman soon led Bulgaria to turmoils which had negative effect on the Bulgarian state-political presence in Macedonia. The right of the new Tsar Boril to rule the country was challenged by his brother Strez who declaired himself an independent ruler of Vardar Macedonia and by Boril's cousin Alexius Slav who took hold of the Rhodopes and Pirin Macedonia. The worst of all was that following their reckless desire to defy Boril they placed themselves at the service of hostile powers who strove to take as much of Macedonia as possible - Strez asked the Serbian king for help while Alexius Slav acknowledged himself a vassal of the Latins and later he became related to Theodore of Epirus, proclaimed as "Emperor of the Romans" - de facto King of Thessalonica. Gradually by 1224 most of Macedonia was included within the boundaries of Theodore's state only the region of Melnik still belonged to Alexius Slav but he was more a friend of Theodore than of his relative - the new Bulgarian Tsar John II Asen (1218-1241). It was not until the Battle of Klokotnica on 9 March 1230 that the Bulgarians regained their control over most of Macedonia with the exception of the region of Thessalonica which was ruled by Manuel Angelus Comnenus - Theodore's brother but Tsar John II Asen's son-in-law and vassal.
After the death of John II Asen in 1241 the power of Bulgaria weakened as a whole so did its influence in Macedonia. As early as the next year Nicea which again set foot on the Balkans mainly thanks to the help of Bulgaria started systematically taking hold of the region of Thessalonica. Especially grave were the consequences of the coup d'etat in Turnovo in 1246 when the rule was taken by the “pro-Nicean” group around John II Asen's second wife Irene Comnenos and her son Michael II Asen. Shortly after that John III, the emperor of Nicea, took at first the regions of Serres and Melnik, then the regions of Struma, Bitola, Skopje and even Velbuzd and all this without any resistance or reaction on the part of Bulgaria. Thus the Bulgarian rule in Macedonia was completely destroyed and the region was divided between Nicea and Epirus. In 1254 emperor John III managed to drive the Epirotes out of Voden, Kastoria, Devol, Prilep, Veles and Ohrid. It was not until his death that the Bulgarians in Macedonia rebelled against the Niceans and tried to restore the rule of the Bulgarian state in the region. But the rebellion led mainly by Dragota, the chief of Melnik, failed and this was the last serious attempt to bring Macedonia back within the boundaries of medieval Bulgaria.
From that moment on the Bulgarian medieval state was no longer to decide or influence the fate of its population in Macedonia with one only exception. In fact after 1255 the Byzantine power in Macedonia considerably strengthened and it was not the Bulgarians who resisted it but the Serbs whose presence here became increasingly sensible. It is no chance that the evidence defined the Bulgarian Tsar Constantine Tih who ascended to the throne in Turnovo supported by the Greeks as a half-Serb descended from Skopje. Even the Inscription of Bojana Church lays particular stress on the Serbian origin of Sebastocrator Kalojan „ the Tsar's cousin". In fact the Serbs made their first attempts for military invasion in Macedonia shortly after the Bulgarian abortive rebellion. In 1257 a Serbian troop passed through the region of Skopje and Kicevo then it laid seige to Prilep as allies of the Epirotes.
By the beginning of the 1280's the restored Byzantine empire was still holding the whole region of Macedonia under its rule. But when the energetic King Milutin (1282-1321) ascended to the Serbian throne things went wrong for the Byzantines. In two years' time after an extremely agressive campaign the Serbians took Skopje and all the Northern Macedonia up to the line Strumica - Prilep - Ohrid which became the new boundary between Serbia and Byzantium. The Bulgarian state under the rule of the Tsars George I Terter and Smilec as the Byzantine writer Pachymeres put it „was not able to help itself let alone help someone else". In fact the marriage between Milutin and the Bulgarian princess Anna Terter seems to show that the Bulgarians acquiesced the Serbian agression in Macedonia. And Milutin kept on expanding his territory - in 1297 he took Western Macedonia and part of the Albanian coast. The only reponse to this action on the side of Tsar Smilec's widow was to make a futile and humiliating attempt to offer her own self as Milutin's new wife. But the Serbian king decided to stake on the more favourable (though scandalous) marriage with the six years old Byzantine princess Simonida Palaeologos. Thus the traditional Serbian-Byzantine alliance attained not only its usual anti-Bulgarian political purpose but from now on it was based on territorial-political deal between the two countries at the expense of the Bulgarian population in Macedonia.
An attempt to shatter this statusquo pernicious for the Bulgarians made Tsar Theodore Svetoslav. In 1304 he waged a war against Byzantium after he had made an alliance with the Catalanian mercenaries in Thrace who later crossed into Macedonia. But the Byzantines foresaw the great danger and managed to keep the situation in Macedonia unchanged by making important concession in Thrace.
From the beginning of 1320's on important political changes took place in all the Balkan countries: in Byzantium one of the heaviest civil wars began - the war between the two emperors both called Andronicus - a grandfather and his grandson started fighting for the throne; in Serbia too a civil war began after Milutin's death - his sons faught for the throne, but it was quite easily taken by Stefan Decanski; in Bulgaria after the tragic doom of George II Terter the dynasty changed again, but the rule was once again stabilized when in 1323 the Despot of Vidin Michael III Sisman Asen ascended to the throne in Turnovo. Gradually Serbia and Bulgaria took a different and contrary stand in relation to the civil war in Byzantium - this time it seems the Bulgarians took the side of the successful younger claimant Andronicus III while the Serbs sided with old Andronicus II. But the Bugarian Tsar did not gain much though he had chosen the winning side. That's why he decided to take the extraordinary opportunity of turning the Serbs out of Macedonia with the help of Byzantium. But the new emperor was only urging Bulgarians and Serbs against each other waiting to see what would happen. The Serbs themselves were feverishly looking for allies and mercenaries while the Bulgarian Tsar was overboldly carrying out military demonstrations between Vidin and Sofia contented with some insignificant help rendered by Vlachs and Tatars paying no attention to the possibility to win over such an outright and powerful Serbian enemy as the Hungarian king Charles Robert of Anjou. That was the reason why the clash between the Serbs and the Bulgarians on 28 July 1330 near Velbuzd was such a disaster for Bulgaria and its ruler who met his death in that battle. The worst was the effect on the Bulgarian policy towards Macedonia - it completely disappeared while Bulgaria itself sank to the level of an inferior political factor on the Balkans gradually overshadowed by Serbia.
And indeed from that moment on there was hardly an important event on the Balkans that the new Bulgarian tsar John Alexander (1331-1371) did not discuss with his Serbian colleague Stefan Dusan (1331-1355) who became his son-in-law marrying his sister Helen (Jelena). The position of Serbia defined the position of the Bulgarian ruler, i.e. the state position. It is not difficult to see that Bulgarian politics favoured Serbia but the interests of Bulgaria were most severly affected by the Serbian expansion in Macedonia which was carried out at least with John Alexander's implicit consent. That's why the Serbian king almost immediately started his offensive in Eastern Macedonia at first. He conquered Strumica and reached Amphipolis. In 1334 the Serbs took Prilep, Ohrid and Kastoria and for the first time seriously threatened Thessalonica. Soon after that Byzantium admitted Serbs' new acquisitions and drew the new boundary almost along the same line which was to be the Greek-Yugoslavian border in 1919. In fact this division of Macedonia in the 14th century served as a basis of the secret Greek-Serbian agreement on the eve of the Balkan wars in 1912-1913 which as it was in Middle ages was directed against Bulgaria and mainly against its interests in Macedonia…
When Emperor Andronicus III died in 1341 the Serbian ruler decided that the treaties were inoperative and he could continue his expansion in Macedonia. Taking advantage from the new civil war in Byzantium the Serbs advanced to the south and in 1342 they conquered Voden (Edessa) and Lerin (Fiorina), in 1344 - the stronghold of Veria, in 1345 - Serres and all the Eastern Macedonia. As a matter of fact the Serbian ruler did not questioned the Bulgarian character of the newly conquered lands as his new official signature proves:
"Stefan, by the Christi God true King of all Serbian and maritime provinces and of the Greek and Bulgarian confines". Soon after that his self-confidence obviously grew so much that on 16th April 1346 he declared himself „Tsar of all Serbs and Greeks" and in the old Bulgarian capital of Skopje he was given the Tsar's crown and not only by the Archbishop of Serbia but also by the Patriarch of Turnovo and there were other Bulgarian bishops there to give him their blessing while in the same time the Bulgarians disappeared from his title obviously quite tendentiously! Soon after the coronation the Serbian tsar divided the newly Conquered lands in Macedonia just like a real emperor among his entourage - the largest parts were given to John Oliver in the region of Ovcepolje and the brothers Mladenovic in the regions of Ohrid and Velbuzd-Kumanovo.
It was not until 1350 that the Emperor John VI Cantacuzenus decided to drive the Serbs out of Southern Macedonia at least using the help of the Turks - the success was short-lived and the mostly Bulgarian local population was brought to ruin by the Turkish mercenaries.
Soon after that fatal events were to change the fate of all the Balkans - in 1354 the Ottoman Turks firmly set foot on the European continent having conquered the strategic stronghold of Gallipoli; soon after that John Cantacuzenus was driven to abdicate, a year later the Stefan Dusan died - and those seemed to be the first signs of the forthcoming calamity of the Balkan Christianity and the expansion of the Islam. In the same time the death of the powerful Serbian ruler led to the disintegration of his empire which affected first of all Macedonia. Dusan's widow - the ex-Bulgarian princess Helen established herself in the region of Serres ruling it on the behalf of her son - the imbecile Tsar Stefan Uros; Southern Macedonia was ruled by Dusan's half-brother Symeon Uros Palaeologus (Sinisa) later it was taken by Radoslav Hlapen; in Vardar Macedonia the brothers Vukasin and Ugljesa Mrnjavcevic gained a footing, while in the regions of Struma and Velbuzd Despot Dejan's sons John and Constantine firmly established themselves. Thus Macedonia was divided into several Serbian principalities and the Byzantine power was established in the region of Thessalonica and some southeastern and southern parts. In 1360's the brothers Vukasin and Ugljesa proved to be the strongest - the first one declared himself a king in Skopje while the second one went to Queen Helen in Serres where he was honoured with the title of despot. In fact a Serbian chronicle from the 15th century is quite indicative describing how the king of Serbia „gave the two brothers to rule the Bulgarian kingdom". One of the earliest Albanian chronicles defines Vukasin as a „king of Bulgaria". Gradually the two brothers were involved in the next Serbian civil war and at the face of the ever growing Turkish threat at that. It was not until 1371 that they decided quite overboldly to stop the Turks to Marica river but they suffered an utter defeat at Cernomen (today's Ormenion). Their defeat did not bring the Turks in Macedonia right away as it has been stated but it caused great changes which prepared the ground for this there.
In fact the Byzantines gained most of all at first driving the Serbs out of Southern and Eastern Macedonia. The Serbs had great losses not only in the principality of Serres hut also in „Vukasin's kingdom" - Vukasin's successor King Markov spite of his great claims and immense popularity" lost everything except the lands around Prilep and Debar and at the end died in 1395 serving as a Turkish vassal and ally against the Hungarians and Vlachs. At the same time the Albanians appeared in Macedonia and two Albanian clans - Gropa and Muzachi - conquered Ohrid and Kastoria.
Among the Serbian principalities in Macedonia the brothers Dejanovic (Dragas) gained most of all after the disastrous Cernomen battle. They were the first to aknowledge themselves as Turkish vassals (in 1372) and expanded their territories towards Strumica, Petric, Melnik, Ovcepolje, Stip, Radovis, Tikves as far south as Dojran, they also took Velbuzd and Vranje. Just like King Marko the youngest of the Dragases - Constantine remained a loyal ally of the Turks right to the end of his life in 1395. The Turks called their friend, the Serbian despot of Velbuzd, Kyostendil and paradoxical as it may seem this name is still used today to indicate the town that grew in the place of the medieval Bulgarian town of Velbuzd.
The invaders managed not only to make the Serbian and the Byzantine rulers Turkish vassals but as early as 1380's they also managed to conquer some of the most important strongholds in Southern Macedonia. On 19th September 1383 Serres was taken and Thessalonica was besieged when its ruler Manuel II Palaeologus declined his vassal dependence. In summer 1385 the Turks captured Stip, Veles, Prilep and Bitola and soon after that Veria and Kastoria. After the Battle of Kosovo in 1389 the pressure against Skopje increased and at the end of 1391 - the beginning of 1392 the Turks managed to take the town. They immediately settled there a great number of Ottoman Turks. Thus Skopje became the first big Muslim centre in the Western Balkans (Turkish name Uskub) - a springboard for the Turkish expansion to the north and northwest.
The fate of Thessalonica and its region in the end of the 14th and the beginning of the 15th century was slightly different from the fate of the other parts of Macedonia. The main town of Macedonia region was captured for the first time by the Turks in 1387 after four years of siege. The local government however as in many other places was left in the hands of the local Christian population though it was not spared the horrible blood duty called „devsirme" thanks to which was recrouted the famous corps of Janissaries. That's why when the inhabitants of Thessalonica heard of the great defeat Bayezid I suffered near Ankara in 1402 against the Tatars led by Timur (Tamerlane) they rebelled and gained their freedom. Soon after that the first Bayezid's successor Suleyman I consented officially to give Thessalonica back to Byzantium if the empire helped him win against his brothers. Later the land was divided between the members of the emperor's family and Thessalonica was given under the rule of the co-Emperor John VII Palaeologus - son of Andronicus IV and the Bulgarian princess Kera Tamara, John Alexander's daughter.
After John's death in 1408, the Emperor Manuel II Palaeologus gave Thessalonica under the rule of his son Despot Andronicus who was ailing and weakling and could do nothing to strenghten the main city in Macedonia - second of importance in all the empire. In 1422 the new Turkish sultan Murad II laid a long and heavy siege to Thessalonica which at the end left its inhabitants without any hope for salvation. Next summer Despot Andronicus and the municipality of Thessalonica decided to commit the government of the town to the Venitians hoping that they Would help against the merciless foes. But the Venitians too acted inconsistently and hesitatingly - they could neither defense the town effectively nor rule it properly and gradually they antagonized the inhabitants of Thessalonica. On 26 March 1430 the sultan's troops who had laid a passive siege till now started a direct assault against the town to capture it. Three days later Thessalonica was taken by the Turks and thus the whole Macedonia was conquered.