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European Kingdoms

Eastern Europe


Asens of Bulgaria / Second Bulgarian Empire
AD 1185 - 1280

The seventh century AD '(First) Bulgarian Kingdom' largely prospered during the eighth and ninth centuries, following a mass migration from the eastern Pontic steppe. It gradually solidified into a medieval state, expanding outwards to occupy much of the Balkans.

Subsequent anarchy in the Eastern Roman empire during the tenth century allowed the ruling prince, Simeon, to besiege Constantinople in 913 until its internal struggle to find a new emperor also resulted in Simeon himself being accepted as emperor of the Danubian Bulgarians. His kingdom was now raised to become the '(First) Bulgarian Empire'.

Simeon's empire was successful, expanding even further and bringing the early Serb state under his direct control. When Pannonia's recently-arrived Magyars began venturing southwards to raid into Bulgaria, he tamed them too, settling friendly groups on the northern bank of the Danube.

The Kievan Rus proved a far more difficult prospect, however. Bulgaria seemed to be at a loss when it came to defeating them, so Simeon's second successor, Boris II, was left with no choice but to ally himself with them. Disaster followed, with a Eastern Roman-Rus war being fought out around the Bulgarian capital, destroying it and seeing Boris captured. The empire was ended.

With much of Bulgaria now under Eastern Roman control, only the west remained independent. Bulgarian governors still maintained control there, most notably under a noble family which was led by four brothers. They were the Cometopuli, the 'sons of the count', and they ruled in the name of the captive Tsar Boris.

While initially successful at establishing a firmly independent Bulgaria state, largely located in what is now Serbia, they later descended into dynastic squabbling and the state was conquered in 1018. Subsequent rebellions against Eastern Roman control failed to do much more than extend the bloodshed, with the last of those rebellions failing in 1073.

By 1185-1186, however, the Eastern Roman empire was at a low point, having declined since it had been defeated by the Seljuqs of Rum at the Battle of Myriocephalon in 1176. Triggered by a rise in taxes, the Bulgarian Asens, local feudal lords, now rose in rebellion against the empire's domination to declare a new independent Bulgar state.

Claiming the mountains of the theme of Paristrion (the heartland of the early Danubian Bulgar kingdom), they quickly expanded outwards from there, while also maintaining the title of tsar. The origins of those rulers are obscure, with modern claims linking them to the Cumans, Bulgars, and Vlachs. The latter may have the best basis, but even so, this was a Bulgarian state leadership for a blended Bulgar-Slav-Cuman-Serb-Vlach population.

The Balkans Mountains in Albania, by wiredforadventure.com

(Information by Peter Kessler, with additional information from The Bulgarians: from pagan times to the Ottoman conquest, David Marshall Lang (Westview Press, 1976), from The Turks in World History, Carter Vaughn Findley (Oxford University Press 2005), from The History of the Medieval World: From the Conversion of Constantine to the First Crusade, Susan Wise Bauer (2010), from An Introduction to the History of the Turkic Peoples, Peter B Golden (1992), and from External Links: Bulgaria (Worldstatesmen), and Encyclopaedia Britannica, and Encyclopaedia Iranica, and the Turkish Cultural Foundation.)

1185 - 1196

John / Ivan I Asen

State recognised by Eastern Romans (1187). Murdered.

1185 - 1196

Peter / Teodor II Asen

Brother and co-ruler. Divided the state in 1192.

1185 - 1186

The Asen brothers, Ivan and Teodor, have requested that the new Eastern Roman emperor, Isaac II Angelus, grants them an estate in the mountains of the theme of Paristrion. His refusal and humiliation of them prompts them to declare a rebellion and grab the land by force. They claim the title of tsar and continuation from the (First) Bulgarian empire.

Ivan Asen of Bulgaria
Ivan Asen leads his troops in revolt against Eastern Roman occupation of Bulgaria in this modern artistic recreation

The emperor immediately has them defeated and routed in battle. They seek refuge with the Cumans in April 1186, returning that autumn with Cuman troops. Paristrion is captured and turned into the new Bulgarian state. Regular raiding into Eastern Roman territories naturally follows.


When Tsar John II (Ivan) is murdered by a boyar (noble), Tsar Peter (Teodor) assigns his half of the state to a younger brother, Kaloyan. Peter himself is murdered the following year.

1196 - 1197

Peter / Teodor II Asen

Now senor ruler. Murdered in unclear circumstances.

1196 - 1197

Kaloyan / Ioanitsa

Brother and co-ruler.

1197 - 1207

Kaloyan / Ioanitsa

Former co-ruler. Stopped Fourth Crusade's advance (1205).


The capture of Constantinople is the Fourth Crusade's 'success', and Latin emperors are established in the city. The Eastern Romans withdraw to Nicæa in Anatolia, but rival claimants also establish holdings in Trebizond and Epirus so that, at one point, there are four claimants to the Eastern Roman throne, as well as the Bulgarian and Serb states.

Close allies of Constantinople through intermarriage and trade, including Alania and the Rus, are badly affected by this disaster.

A reconstruction of medieval Kyiv
Kyiv's great territory, its competing junior princes, and its exposure to successive waves of mounted invaders from the eastern steppe eventually resulted in the decline of Kievan Rus power overall, not just in Kyiv itself

In the same year, the Pope acknowledges Kaloyan as 'King of the Bulgarians and Vlachs', although Kaloyan himself maintains the title of tsar. It has taken some work to achieve this recognition, with it being protested by Serbs and Hungarians.

The addition of Vlachs reflects the multicultural nature of Bulgarian lands by this time (albeit that they were always so, with even the formerly tribal Bulgars being assembled from a multi-tribal collective).


With the Fourth Crusade having splintered control of the lower Balkans into many pieces, the powerful Tsar Kaloyan is able to make good progress in expanding his empire. The Battle of Adrianople on 14 April 1205 sees Baldwin IX of Flanders, master of Constantinople, being defeated before being captured and taken into captivity where he dies.

1207 - 1218


Nephew by a sister. m Kaloyan's widow & seized throne.


With the unexpected death of Kaloyan, his unnamed sister's son, Boril, marries Kaloyan's Cuman widow and seizes the throne. Ivan Asen, the son of Tsar Ivan I and a rival prospect for the throne, flees the country to safeguard his own life, but the act also strengthens Boril's position.

South Struma Valley
The South Struma Valley, showing the kind of territory the Romans and Bulgarians alike had to defend or attack, depending upon the prevailing political situation

Boril does not have things entirely to his liking though. A senior noble and cousin by the name of Strez refuses to acknowledge him. He takes possession of the lands between the rivers Struma (the ancient Strymṓn) and Vardar (the Axios), both in what is now southern Bulgaria.

Another Asen noble, Alexius Slav, secures the Rhodope Mountains. However, Boril survives in power until Ivan Asen returns to capture and blind him.

1218 - 1241

John / Ivan II Asen

Cousin. Son of Ivan I. Seized throne.


A large Mongol force under Subedei enters territory around the Caspian Sea and then the land of the Rus. Rus and Cuman forces assemble which greatly outnumber Subedei's men, but they are defeated at the River Khalka.

Subedei extends his expedition farther to attack the Volga Bulgars, while a large subsequent Cuman exodus into Hungary also results in many of them finding refuge in Bulgaria (sometimes to be faced with Bulgarian-led massacres).

River Kama
The River Kam (Kama) joins the mighty Volga just below the site of Kazan, founded as a border post by the Volga Bulgars to keep a watchful eye on the neighbouring Volga Finnic tribe of the Mari and the Bjarmian Udmurts


Ivan II wins the Battle of Klokotnitsa, crushing the forces of Theodore Komnenos Doukas (Ducas) of the empire of Thessalonica, which he commands after having moved his stronghold from Epirus.

Theodore's empire soon collapses, allowing Ivan Asen to take possession of great swathes of Macedonia, Thessaly, and Thrace. Theodore himself is captured and held for the next seven years while his brother, Michael, takes command of his remaining territories.

1242 - 1246

Kaloman / Kaliman / Calojoannes I

Son. Acceded age 7. Poisoned?


A Mongol force under the command of Kadan, son of Ögedei Khan, enters Bulgarian lands. Archaeological evidence shows that at least a dozen forts are burned in this period, and the Bulgarians are forced to accept that they will have to pay tribute. The Mongols are content to leave the Bulgarians alone afterwards though.

Mongol warriors
Within just thirty years, Mongol warriors had travelled as far afield as central China and Eastern Europe, and south-west into Persia, turning the Mongol empire into the largest single controlling force in history

1246 - 1256

Michael II Asen

Half-brother. Acceded age 7. Murdered by Kaloman II.


Kaloman / Kaliman / Calojoannes II

Nephew of Ivan II. Usurper. Dethroned & murdered.

1256 - 1257

Mitso Asen

Son-in-law of Ivan II. Not popular. Fled the capital.

1257 - 1277

Constantine Tich / Tikh / Tih

Serb-Bulgar noble. Part-paralysed. Killed during revolt.


The Nicæan-Latin Wars are not concluded when Michael VIII Palæologus of Nicæa recaptures Constantinople, as Achaia and Athens are still occupied by Latin rulers. The city falls during a surprise attack when much of the garrison is raiding Nicæan territory.

The Latins are helped in their largely successful evacuation by the Venetian fleet, but Michael VIII is able to claim Constantinople as his seat and the capital of the Palæologus. Unfortunately the claim to the throne which is held by the eleven year-old John IV Lascaris is sidelined when the boy is blinded and imprisoned by Michael.

Marco Polo on the Silk Road
Marco Polo's journey into China along the Silk Road made use of a network of east-west trade routes which had been developed since the time of Greek control of Bactria


Having failed to establish friendly relations with many of his neighbours, Constantine seeks help from the Mongols. A force which consists of thousands of Tartars crosses the lower Danube to invade Eastern Roman territory in alliance with the Bulgarians. Michael VIII of the Palæologus loses some territory but remains on the throne. Subsequent Mongol raids also target Bulgaria, weakening it severely.

1269 - 1279

Maria Palaiologina Kantakouzene

Wife. Dau of Michael VIII Palæologus. Empress consort.

1278 - 1279

Ivalio / Ivaylo

Commoner. Led revolt. Briefly recognised. Exiled & killed.


Ivalio's successful peasant rebellion sees him marrying Maria Palaiologina Kantakouzene, widow of the late Tsar Constantine, in order to cement his control in the face of hostile forces on all sides of Bulgaria's borders.

Michael VIII Palæologus supports Ivan III in an attempt to claim the throne, even giving him troops to do so. Ivalio travels to the Mongol capital to gain support there, but Ivan also proceeds there to ensure that the Mongols favour his seemingly better claim of legitimacy. Ivalio is killed while the Bulgarians exile Maria to Constantinople.

Byzantine icon
An icon showing four episodes from the life of Christ which was probably painted in Thessalonica, the most important artistic centre in the crumbling Eastern Roman empire after Constantinople

1279 - 1280

John / Ivan III Asen

Son of Mitso Asen. Abandoned throne (1280). Died 1303.

1279 - 1280

Ivan's hold over the territory of the Bulgarians is somewhat tenuous in places, especially prior to Ivalio's unwise journey to the Mongol capital. In order to remedy this he marries his sister, Maria, to the Bulgo-Cuman nobleman, George Terter. This fails to have the intended impact however.

Ivan and his own wife, Irene, another daughter of Eastern Roman Emperor Michael VIII Palæologus, flee an Ivalio siege to seek refuge in Constantinople. They take with them whatever Bulgarian riches they can carry, but their arrival enrages Michael VIII who had been supporting them towards ensuring a secure and friendly Bulgaria.

Ivan subsequently proceeds to the Mongol capital to contest the throne with Ivalio. The Mongols select Ivan but fail to restore him to the throne, leaving the way open for the 'Second Empire' Terter dynasty under George Terter.

Terters & Shishmans of Bulgaria / Second Bulgarian Empire
AD 1280 - 1395

The Bulgarian presence in the Danubian delta region began with the seventh century Danubian Bulgar kingdom. Early tenth century anarchy in the Eastern Roman empire allowed the ruling prince, Simeon, to become the (First) Bulgarian emperor. The arrival of the Kievan Rus into the fevered political mix in the Balkans of the late tenth century proved to be the empire's undoing, however, with only the Cometopuli territories in the west of the empire surviving to oppose Eastern Roman occupation.

While initially successful at establishing a firmly independent Bulgarian state, the cometopuli later descended into dynastic squabbling and the state was conquered in 1018. Subsequent rebellions against Eastern Roman control failed to do much more than extend the bloodshed. By 1185-1186, however, the Eastern Roman empire was at a low point, which allowed the Asens to rise in rebellion and declare a new independent Bulgar state.

Eventually only the Terters could offer firm leadership for the Bulgarians. This was in the form of the Bulgo-Cuman nobleman and Eastern Roman despot, George Terter, seemingly descended from the Cuman Terteroba clan, although few details are known about his origins. His reign as tsar initially offered the Bulgarians hope of strong leadership, but ultimately Mongol dominance of the region proved too strong. Instead Bulgaria gradually deteriorated as a power as internal anarchy spread and cross-factional fighting increased.

Initially, Terter Bulgaria amounted to little more than the original territory of the Danubian state, although it had expanded greatly by the time of Theodore Svetoslav, stretching westwards along the Danube. He and his successors largely established Bulgarian borders which survive to this day, albeit with many post-Ottoman amendments. The Terters were succeeded by the Shishman family.

The population of Bulgaria had always been mixed, initially comprising of Bulgars (themselves a hotch-potch of various strands of early Turkic tribes) and Slavs who had settled the Danubian delta a relatively short time before the Bulgars arrived there.

By the eleventh and twelfth centuries the local population also comprised of populations of Cumans, Serbs, and Vlachs. The Bulgar Turkic language had long since been replaced by Slavic, and the Bulgar state had vacillated for a time between the Latin alphabet and the new Cyrillic one, before it plumped for the latter.

The Balkans Mountains in Albania, by wiredforadventure.com

(Information by Peter Kessler, with additional information from The Bulgarians: from pagan times to the Ottoman conquest, David Marshall Lang (Westview Press, 1976), from The Turks in World History, Carter Vaughn Findley (Oxford University Press 2005), from The History of the Medieval World: From the Conversion of Constantine to the First Crusade, Susan Wise Bauer (2010), from An Introduction to the History of the Turkic Peoples, Peter B Golden (1992), from The Late Medieval Balkans: A Critical Survey from the Late Twelfth Century to the Ottoman Conquest, John V A Fine (University of Michigan Press, 1994), and from External Links: Bulgaria (Worldstatesmen), and Encyclopaedia Britannica, and Encyclopaedia Iranica, and the Turkish Cultural Foundation.)

1280 - 1292

George / Gergi I Terter

Roman despot. Seized power. Died 1308/1309.


Having hurriedly arranged an anti-Eastern Roman alliance with Stefan Dragutin of Serbia, Charles I of Naples, and also with Thessaly, George almost immediately finds it failing. Charles is faced with the potential loss of Sicily and is distracted, while the Bulgarians are ravaged by Nogai Khan and his Nogai Horde division of the Golden Horde.

Tsar George Terter I coin of late 1200s
The obverse of this coin was issued during the twelve year reign of George Terter, seemingly imitating a Venetian grosso


Following another damaging attack by Nogai Khan, George is apparently removed from the throne. He accepts exile, travelling to Adrianople, while his place is taken by Smilech.

After a long wait, George is finally accepted into the Eastern Roman empire by Andronicus II and spends much of the last decade of his life in obscurity in Anatolia (in 1301 he becomes part of a prisoner exchange which is organised by Theodore Svetoslav).

1292 - 1298

Smilech / Smilets

Noble. Vassal of Nogai Khan. 'Removed' from power.


Smilech is largely a pawn of Nogai Khan, but at least his reign sees Nogai's raiding largely confined to Eastern Roman territory. He is removed from the scene in 1298, although the circumstances are unknown.

The suspect is generally thought to be Nogai Khan or his son, Chaka, both of whom are heavily involved in a struggle for control of the Golden Horde. His replacement, Ivan IV, is also referred to as Ivan II, which ignores two out of three of his Asen predecessors on the throne.

Mongols of the Golden Horde
The Mongols maintained their dominance of the Bulgarians with bloodletting where necessary, burning and destroying towns which stood against them

1298 - 1299

Ivan IV (II)

Son. Aged about 8 at accession. Removed and exiled.

1299 - 1300

The power struggle between Toqta of the Golden Horde and Nogai Khan of the Nogai Horde flares up into open conflict, and Toqta is the victor in 1300. Nogai's son, Chaka, flees first to the Alani and then to Bulgaria where he has already (briefly) gained the throne as emperor. The young Ivan has been removed to spend the rest of his life in exile in the Eastern Roman empire (until about 1300).

1299 -1300

Chaka / Caka

Son of Nogai Khan of the Mongol Nogai Horde. Killed.


With the Bulgarians aware of the anger of Toqta of the Golden Horde at the position Chaka holds, Theodore Svetoslav sends Chaka's head to his Mongol overlord and replaces Chaka on the Bulgarian throne. As a result of this cooperation, Mongol interference in Bulgaria largely ceases.

1300 - 1322

Theodore Svetoslav

Son of George I. Fought off pretenders but ensured stability.

1322 - 1323

George II Terter

Son. Died of natural causes. No heir.

1323 - 1330

Michael III Asen / Shishman

Cousin. First Shishman family tsar.


Michael Asen, using the name to link his reign to the preceding Asens, normally known as Michael Shishman, his family name, has pursued an aggressive policy of establishing Bulgaria as the leading power in the Balkans. Having agreed an alliance with Eastern Roman Emperor Andronicus III, he organises a major attack against the Serbs.

George Terter II coin
This photo shows both sides of a coin which was issued during the reign of George Terter II, although the mint location appears to be unknown

Poor coordination with the Eastern Roman forces means that Michael faces a Serb army which is equal to his in numbers. The Serbs are quickly reinforced before battle commences near Velbazhd (now Kyustendil in Bulgaria). Michael is defeated and dies within a few days, either mortally wounded or in some way badly hurt and unable to recover.

1330 - 1331

John / Ivan Stephan

Son. Removed by a coup.

1331 - 1371

John / Ivan Alexander

Cousin. Stabilised the state.


With the Eastern Roman civil war having been concluded, Emperor John Cantacuzenes has realised the threat posed by the Ottoman Turks. His attempts to form a united front alongside the Serbs and Bulgarians are rebuffed, however. This is despite Tsar Ivan Alexander already having lost a son and brother to Ottoman raids.

In fact, Alexander makes things worse by creating two co-ruling principalities within Bulgaria, the second of which - Vidin - becomes fully independent in 1371, weakening the state as a whole.

Ottoman Bulgaria
The arrival of the Ottoman Turks in the Balkans added yet another layer of ethnic diversity into an already-rich Bulgarian ethnic mix

1356 - 1365

Ivan Stratsimir

Son & co-tsar. In Vidin (NW Bulgaria). Deposed by Hungary.

1369 - 1396

Ivan Stratsimir

Restored in Vidin by Hungary. Fully independent (1371).

1371 - 1395

John Shishman

Brother. Ctrl Bulgaria only. Captured. Killed. End of empire.

1387 - 1388

The principality of Serbia and the kingdom of Bosnia manage to unite their forces in 1387 to inflict a defeat upon the Ottomans at the Battle of Pločnik. The European victory emboldens other rulers, including John Shishman who refuses to send troops to support his nominal overlords.

The Ottoman response is to send a thirty thousand-man army into Bulgaria in 1388. John Shishman has proven himself as the only one of the three Bulgarian rulers who openly and consistently opposes the Ottomans, but he pays the price.

Losing fortress after fortress to his enemy and not receiving support from his neighbours, he has to reconfirm his vassalage under harsher conditions and with an occupying Ottoman force.

Map of the Timurid empire AD 1400
With Persia thoroughly focussed on resisting the ever-expanding conquests of Timur in the late 1300s, the Ottomans were largely free to focus their attentions on defeating the states of the Balkans, but Timur's completion of his task by 1401 changed that situation completely (click or tap on map to view full sized)


Having learned that John Shishman is secretly planning an alliance with Hungary, the Ottomans send a large army into the field. It captures the Bulgarian capital at Tarnovo while Shishman is in Nicopolis, and Bulgaria as a whole is subject to devastating raids and destruction.


Nicopolis is captured by the Ottomans after a surprise approach from the north. Sultan Bayezid summons John Shishman under the pretence that discussions will be held regarding the position of the Bulgarians. Instead Shishman is seized and beheaded.


The Battle of Nicopolis results in defeat for the allied European forces. Amongst the participants is Duke Charles II of Lorraine, Count John the Fearless of Nevers, and Tsar Ivan Stratsimir of Bulgarian Vidin.

Venetian and Ottoman troops in the long-running wars between the two
The Ottomans directly challenged the most powerful of Europe's Mediterranean empires in the form of the Venetian republic, leading to a series of vicious wars over the course of three centuries which are known as the Ottoman-Venetian Wars

The defeat means that the Ottomans are able to capture Vidin by the start of 1397 at the latest. Ivan Stratsimir is captured and imprisoned where he is probably murdered. The Bulgarians are now a subject territory of the Ottoman Turks.

1396 - 1878

With European forces remaining poorly coordinated when it comes to opposing the Ottomans, they are able to dominate the south-eastern Balkans. The Bulgarians remain entirely subsumed within the empire, despite a counter-claim by Constantine II.

He is the son of Ivan Stratsimir, and he retains a claim to Vidin until his death in 1422. The claim is generally recognised by neighbouring European states, but little is known of him after 1397, including what territory (if any) he may hold. He is not normally included in lists of Bulgarian rulers.

King Stephen Tomasevic of Bosnia
King Stephen Tomasevic reigned for just two years over an independent Bosnian kingdom which was living on borrowed time, faced by a near-tidal wave of Ottoman attacks which it was ill-equipped to stave off, and a final attack in 1463 which it had no hope of defeating


1828 - 1829

The Russo-Turkish War, triggered by the fighting in Greece and the Danubian principalities, ends in the Peace of Adrianople. The Ottoman sultan closes the Dardanelles to Russian vessels but the Russians lay siege to three major Ottoman cities in Bulgaria.

In the end, despite an embarrassing defeat along the way, Russia wins the mouth of the Danube and much of the Black Sea's western coast under the terms of the peace, or Treaty of Adrianople. Serbia also achieves autonomy.


Following the conclusion of the Russo-Turkish War, territory which includes Moesia and the Sofia region - but not southern Bulgaria (the eastern section of the Ottoman eyalet (province) of Rumelia, otherwise known as East Rumelia) or the Macedonian region - is combined into a newly-formed 'Principality of Bulgaria'. A German prince is elected as head of state.

Prince Alexander of Bulgaria
Prince Alexander of Hessen-Battenberg was largely able and successful in steering Bulgaria's course between fervent nationalist ministerial demands and the pressure from Russia to become little more than an extension of its empire

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