Bulgarian–Ottoman wars

The Bulgarian-Ottoman wars were fought between the kingdoms remaining from the disintegrating Second Bulgarian Empire, and the Ottoman Empire, in the second half of the 14th century. The wars resulted with the collapse and subordination of the Bulgarian Empire, as the last standing Kingdom, the Tsardom of Vidin, was conquered in 1396. As a result of the wars the Ottoman Empire greatly expanded its territory on the Balkan peninsula, stretching from Danube to the Aegean Sea.

The situation in the Balkans on the eve of the Ottoman invasion
From the 13th century, the two main Balkan powers Byzantium and Bulgaria fell victims to a process of decentralization, as local feudal lords grew stronger and more independent from the emperors in Constantinople and Tarnovo. This weakened the military and economic power of the central rulers. The process deteriorated central authority to an even larger extent in the 14th century, when numerous nobles came to be only nominally subordinated to the government. In Bulgaria the powerful Shishman family ruled over the Vidin Province in the west, while in the east Balik established a quasi-independent Despotate of Dobruja.

While the two Empires were facing enormous internal difficulties, the Serbs took the favorable opportunity to expand its domain. During the civil war in Byzantium in 1320s and 1330s, the Serbs conquered most of the Bulgarian and Aromanian populated Macedonia from the Byzantines. In 1330 Serbian forces defeated Bulgarian Emperor Michail Shishman at Velbazhd effectively raising the country to the status of the most powerful state in the region. In 1346 king Stefan Uroš IV Dušan even received the title of Emperor with the blessing of the Bulgarian Emperor Ivan Alexander, although after his death in 1355, the large Serbian Empire disintegrated into a few independent states. In Bulgaria of the same period Ivan Sratsimir inherited Vidin from his father Ivan Alexander in 1356, while despot Dobrotitsa – nominally his subject – ruled Dobruja. Lack of stability was eminent in the southern Balkans as well: in 1341–1347 the Byzantine Empire was shaken by a bloody civil war between John V Palaiologos and John VI Kantakouzenos.

Circa mid 14th century the Balkans were politically disunited into a number of small states frequently in competition with each other and there was no single strong entity with a powerful enough army to withstand the Muslim invaders. In addition to the mainly Orthodox countries such as Bulgaria, Byzantium and Serbia, there were a number of Catholic possessions to the west and south held by Venice, Genova and the Kingdom of Hungary as well as Kingdom of Bosnia whose Bosnian Church (closely related to the Bogomils) was considered heretic by both Orthodox and Catholics. Religious dissimilarity was thus also a source for constant political tensions in the region.

Military actions during the reign of Ivan Alexander
During the civil war in Byzantium both Palaiologos and Kantakouzenos were trying to find external allies and used foreign mercenaries. The Bulgarian Emperor supported the first opponent whose stronghold was Constantinople. John Kantakouzenos on the other hand regularly hired Ottoman Turk mercenaries from Asia Minor who soon became a fixture on the battlefields in Thrace. The Byzantines often lost control over the Ottomans them as the latter regularly plundered villages in the Southern Balkans after the 1320s.

In 1344, Momchil, the independent Bulgarian ruler of the Rhodope and Aegean regions, whose army grew to 2,000 men, took an important role in the Byzantine civil war. While at first he supported John Kantakouzenos, from the spring of 1344 Momchil reneged, provoked by the aggression of the Ottoman allies. In June he defeated the Ottoman fleet near the Portogalos bay. According to sources, at night the Bulgarian ruler sent boats to burn the anchored Ottoman ships and soon after he defeated the army of Kantakouzenos at Mosynopolis.

Probably the first local ruler to become aware of the impending Ottoman threat, Momchil unsuccessfully pleaded both Emperors of Bulgaria and Byzantium for help. Even though his troops continued the resistance in the Eastern Rhodopes, in May 1345 the Turks led by Umur Beg marched from Asia Minor and devastated Bulgarian territories driving away people and livestock. Soon after, on 7 July 1345, Ottoman forces under Umur Beg defeated Momchil's army in the battle of Peritor near his capitalXanthi. Sources attest the independent ruler perished in the battle leaving no successor and little decisive political will to counter the Turk invaders.

During the Byzantine civil wars Ivan Alexander regained control over several towns in Thrace and the Rhodopes but his frequent interference in the internal affairs of Byzantium hampered any closer relations between the two counties despite the peace established in 1332. In 1352 Turkish forces invaded Bulgaria anew, raiding Thrace, particularly the vicinities of Aitos, Yambol, and Plovdiv, and capturing rich spoils. In the same year the Ottomans seized their first fortress on the Balkans, Tsimpe on the Gallipoli peninsula, setting firm foot in Europe. Until 1354 Ottoman forces again ravaged the lands around Yambol and Plovdiv as well as the lower valleys of the Maritsa and Tundzha rivers.

In 1355 the Ottomans launched a campaign towards Sofia, but were promptly engaged by the army of Ivan Alexander's eldest son and heir Michael Asen close to Ihtiman. the Turks prevailed in the following battle, although both sides suffered heavy casualties. Despite the victory and the death of young Micheal Asen, the Turks were unable to reach Sofia.

Unsuccessful alliance
The defeat raised serious alert not only in Tarnovo, but also in Constantinople, forcing John Kantakouzenos to abdicate and removing one of the main perpetrators of the Ottoman invasion. Faced with threat, Bulgaria and Byzantium made an attempt for rapprochement. In 1355 a daughter of the Bulgarian Emperor, Keratsa, married Andronikos, the infant son of new Byzantine Emperor John V Palaiologos. The new relations between the houses of Tarnovo and Constantinople could have been harmful to the invading Ottomans, but despite the anticipation the agreement did not pay off. The Bulgarian and Byzantine Empires of the period were once again the major political powers on the peninsula and the only states able to stop the Ottoman success. After the death of Stefan Dushan on 20 December 1355, the Serbian Empire lost much of its hegemony in the Western Balkans and the large and ethnically diverse empire split into several successor states. Between 1354 and 1364 the Turks ruled Thrace as a number of important fortresses and towns, such as Plovdiv and Stara Zagora fell under attack. From the end of the 1350s Ottoman military units even reached the surroundings of the capital as, according to sources, the Emperor took precautions to strengthen the city walls. Ottoman chronicler Seadeddin suggests that Turkish advance between 1359 and 1364 involved destruction and depopulation of many areas as towns like were devastated (Plovdiv, Stara Zagora, Sliven) while others such as Venets and Sotirgrad were altogether annihilated. Destruction was accompanied by slaughters and deportation of local populace to Asia Minor.

Not only was there a total lack of coordination between the two Empires, but they also quarreled for the Black Sea ports of Mesembria and Anchialos. Bulgaria successfully defended them in 1364, though the war entrenched distrust and animosity between the parties despite the impending danger.

The last years of Ivan Alexander
Apart from the economic devastation and military threat from the south, Bulgaria had other problems: in 1365 the Hungarian King Louis I invaded north-western Bulgaria, seizing the large Vidin fortress and capturing the eldest living son of the Tsar, Ivan Sratsimir. In his futile attempts to reconquer Vidin, Ivan Alexander even resorted to using Ottoman mercenaries. However, in the summer of 1369, the Bulgarian Emperor restored his authority over the Vidin Province with the help of the Wallachian voivode Vladislav I although that proved to be his last success.

After Ivan Alexander's death on 17 February 1371, lands populated by Bulgarians were divided into several independent states. Much of the much of the former territory came under the rule of the tsar's third son Ivan Shishman; northwestern areas were the dominance of the eldest son Ivan Sratsimir, despot Dobrotitsa held Dobruja, while most of Macedonia was divided into several feudal states controlled by Serbian nobles.

Battle of Chernomen and its consequences
In 1371 two feudal lords in Macedonia organised a campaign against the Turks. Serbian brothers Vukashin and Uglesha, respectively the king of Prilep and the despot of Ser, gathered a numerous Christian army aiming to stop the Muslim invaders. Uglesha, whose lands bordered Ottoman territory to the east, realized the threat and unsuccessfully appealed to Serbian and Bulgarian states for help. Ruling over mixed Serbian-Greek-Bulgarian population, the two brothers set off to the east with 20 to 70,000 strong ethnically diverse army. Considerably less numerous troops led by Lala Shahin Pasha attacked the united Balkan forces at night on 26 September as the latter camped by the village of Chernomen in the lower Maritsa valley. The entire army was pushed back and Vukashin and Uglesha perished along with much of their forces.

Immediately after the battle, the armies of Murad I embarked on another campaign overrunning Northern Thrace and forcing young Ivan Shishman to pull back north of the Balkan Mountains. A number of fortresses fell, though after prolonged and fierce sieges: the town of Diampol, for instance, fought against the forces of Timurtash for months but was eventually forced to surrender because of food shortage. One of Ivan Shishman's voivodes, Shishkin, was killed in battle on the southern skirts of the Balkan Mountains further easing the Ottoman conquest of the Rhodopes, Kostenets, Ihtiman, and Samokov. After a bloody siege they captured Bitola in the southwest and soon encroached on the Sofia Valley. In 1373 Ivan Shishman was forced to negotiate a humiliating peace treaty: he became an Ottoman vassal strengthening the union with a marriage between Murad and Shishman's sister Kera Tamara. To compensate, the Ottomans returned some of the conquered lands, including Ihtiman and Samokov.

Between 1371 and 1373 the Ottomans emerged as a considerable power on the Balkans. They ruled over the entire Thrace and had seized the lands of Uglesha in Eastern Macedonia and managed to subordinate Vukashin's son Marko and Ivan Shishman who became their vassals.

The fall of the Rhodopes
During the same period (1371–1373) the invaders took control of the Rhodopes, a mountain studded with strong and well-guarded fortresses, approaching from the north. The Rakovitsa fortress (now in ruins) was besieged by Daud Pasha and fiercely defended by its voivoda Kurt; after futile attempts to capture it with force, the Turks agreed to negotiations and the Bulgarians surrendered keeping their property.

Similarly, the population of Tsepina, one of the strategic fortresses of the Rhodopes, resisted Ottoman attacks for nine months before surrendering in return for their lives and property after Daud Pasha cut off the water supplies. In the same way Stanimaka (Asenovgrad) was taken and soon after fell the northern Rhodopes fortress of Batkun whose commander Georgi died in the final assault.

The Ottomans faced a stubborn resistance in the Rhodopes interior: central areas were invaded by the armies of Dzhedit Pasha and Ibrahim Pasha. The former advanced through the road between Stanimaka and Bachkovo Monastery along the valley of Chepelarska river, while Ibrahim pasha set off from Plovdiv via Parvenets and then through the valley of Vacha River. Fighting occurred at Zarenitsa, Zagrad, Gradishte, Chiltepe and Karakulas (along Vacha), Imaretdere and Momina Voda (heights close to Ardino) among others. Especially ferocious were the engagements at Momina Voda, where prominent Ottoman general Sarǎ Baba was killed, and Karakulas where Enihan Baba perished.

Fall of Sofia
While Ivan Shishman was desperately trying to resist against the strong Ottoman pressure, his brother Ivan Sratsimir not only withheld reinforcements or help but tried to make use of the difficulties which his brother faced to expand his domains over certain areas of the Tarnovo Tsardom. As Shishman's attention was pointed to the south, Ivan Sratsimir took control of the important city of Sofia which was disputed between the two brothers. However by 1373 the city was again in the Tarnovo Tsardom and it is possible that there might have been armed conflict between the two Bulgarian states. Despot Dobrotitsa also did not give any support to the Emperor in Tarnovo. He was in conflict with Genova and was involved in the internal affairs of the Empire of Trebizond trying to put on its throne his son-in-law.

After the temporary hush which followed after 1373, in 1380 the Ottomans again started hostilities. With a large army Sultan Murad headed towards the south-western regions of the Tarnovo Tsardom which main objective to seize its center Sofia. After a bloody clashes in the Zlatitsa valley the Turks moved on to Sofia and besieged it. The city which was commanded by ban Yanuka repulsed all the attacks of the superior Ottoman forces under Lala Shahin. The later could not continue the siege and was forced to pull back to Odrin where he reported his failure to the Sultan. While he was absent the Turks managed to infiltrate Sofia and one Muslim Bulgarian captured ban Yanuke while hunting and sent him to Lala Shahin who was in Plovdiv at that time. From there the Bulgarian commander was sent back to Sofia and when the defenders saw their captured leader they surrendered the city to the Ottomans (1382).

The Ottomans installed a strong garrison and brought Muslim settlers from Asia Minor. On the following year fell Serres The new Ottoman success did not bring together Ivan Shishman and Ivan Sratsimir. Between 1384 and 1386 waged a war between Bulgaria and Wallachia, the Vlachs seized several settlements along the Danube but were later defeated and their voivoda Dan I was killed. Ivan Sratsimir took part in the actions as an ally of the Vlachs which proved the total lack of coordination between the Bulgarian states and deepened the mistrust between the two brothers.

After they secured the possession of the area around Sofia, the Ottomans continued their march to the north-west. The main objective of Murad was to break the ties between Bulgaria and Serbia because despite Ivan Shishman was his vassal, Murad did not trust him and knew that the Bulgarian ruler was waiting for an appropriate opportunity to renege. In 1386 the Turks seized Pirot and Naissus after bitter fights killing and enslaving many Bulgarians.

The campaign of 1388
The advance of the Ottomans in the central parts of the Balkan peninsula caused serious anxiety not only for Ivan Shishman but also in Serbia and Bosnia. The Serbian Prince Lazar and the Bosnian King Tvardko organized an anti-Ottoman coalition and the Bulgarian Emperor joined them but was unable to send troops. In 1387 the united forces of Bosnians and Serbs defeated the Turk in the battle of Plocnik.

However, while the Christian states did not make any attempt to exploit the victory, the Turks' reaction was swift. In 1388 a 30,000 strong army commanded by Ali Pasha passed through the eastern Balkan mountains and struck deep into Bulgaria's north. The Bulgarians were completely surprised and the invaders seized Ovech, Shumen, Madara and other towns. Due to the surprise campaign at first the towns and the castles were unable to organize proper defence but after the initial shock the Bulgarians took precautions. When the army of Ali Pasha besieged Varna, the defenders stiffly resisted and the Turks were forced to abandon the siege and march northwards.

In Tutrakan the citizens allowed the Turks to install a small garrison but then they killed the Turkish soldiers and prepared for siege. Ali Pasha immediately burned the surrounding fields and soon the starving town had to surrender. After this success they advanced to the west towards Nicopolis, one of the strongest Bulgarian fortresses along the Danube. The defence was organized by Ivan Shishman who was currently in the town. Although the Ottomans had nearly 30,000 men they could not take it and Ali Pasha had to seek reinforcements from Murad himself. According to Seadeddin the Sultan marched to Nikopol with an enormous army firmly decided to seize the town at all costs. When Ivan Shishman faced the new enemy he sought a truce. Murad agreed and the Bulgarians saved Nikopol but were forced to cede another key Danubian fortress, Dorostolon. However, when Ali Pasha reached Silistra, the Bulgarians refused to surrender the town. Murad besieged Nikopol for a second time and this time Ivan Shishman agreed to the Ottoman conditions and a Turkish garrison was installed in Silistra.

As a result of the campaign the Turks took most of eastern Bulgaria including several key towns. Now the authority of Ivan Shishman reduced to the lands to the west of the capital Tarnovo and several castles along the Danube. To the east the Bulgarians kept Varna and the capital of the Principality of Karvuna, Kaliakra. Probably at that time Ivan Sratsimir became an Ottoman vassal.

Final conquest
As a result of the Ottoman success in the 1388 campaign and the resulting changes of the balance of power, Ivan Sratsimir had to become an Ottoman vassal and to accept an Ottoman garrison in Vidin. Ivan Sratsimir remained inactive while the Ottomans destroyed the remains of the Tarnovo Tsardom – Tarnovo fell in 1393 and Ivan Shishman was killed in 1395. In 1396 Ivan Sratsimir joined the Christian crusade organised by the Hungarian king Sigismund. When the crusader army reached Vidin the Bulgarian ruler opened the gates and surrendered the Ottoman garrison. The Ottoman garrison of Oryahovo tried to resist but the local Bulgarians managed to capture it. However, the Christian army suffered a heavy defeat on 25 September in the battle of Nicopolis and the victorious Ottoman sultan Bayezid I immediately marched to Vidin and seized it by the end of 1396 or the beginning of 1397. Ivan Sratsimir was captured and imprisoned in the Ottoman capital Bursa where he was probably strangled.

Some Bulgarian historians suppose that the territory of Vidin, or at least some portions of it, may have remained under the rule of Stratsimir's son, Constantine II, almost until his death in 1422. Together with his cousin Fruzhin (Fružin), a son of Ivan Shishman (Ivan Šišman), Constantine II took advantage of the Ottoman Interregnum to raise an anti-Ottoman revolt in northwestern Bulgaria. Constantine II was also allied to the Serbian despot Stefan Lazarević and the Wallachian voivode Mircea I. The anti-Ottoman rebellion lasted for half a decade (1408–1413) and spread to much of Bulgaria until the rebels were defeated by the Ottoman Sultan Musa.