Michael Shishman of Bulgaria

Bulgaria during the rule of Michael Shishman.

The sudden death of George Terter II had been followed by a brief period of confusion and uncertainty, which was exploited by the Byzantine emperor Andronikos III Palaiologos. The Byzantines overran northeastern Thrace and captured a number of important cities including Yambol, Lardea, Ktenia, Rusokastro, Anchialus, Sozopol and Agatopol. At the same time, a Byzantine-sponsored pretender, Voysil, brother of the former Bulgarian emperor Smilets (r. 1292-1298), ensconced himself in Krăn, controlling the valleys between the Balkan mountains and Sredna Gora from Sliven to Kopsis.[7] At this point the newly elected Michael Shishman marched south against Andronikos III, while another Byzantine army led by Andronikos III himself was besieging Philippopolis (Plovdiv). Defended by a Bulgarian garrison led by Ivan the Russian, the siege was a failure despite the Byzantines use of a 100-soldier, five-story siege tower.[7][8] While the Byzantine army was engaged at Philipopolis, Michael Shishman led his troops to north-eastern Thrace and quickly retook the lost cities thus forcing the Byzantines to pull back.[7]

Although Michael Shishman forced Andronikos III to retreat, the Byzantines managed to take the Philippopolis while the Bulgarians were changing garrisons.[9] Despite the loss, Michael Shishman was able to expel Voysil and fully recover Bulgarian control over northern and northeastern Thrace in 1324 which had been taken by the Byzantines in the previous year during the interregnum.[10] Again in 1324, the Bulgarian emperor invaded Byzantium advancing as far as Traianopolis^[b] and Vira in the lower course of the Maritsa river.[11] Andronikos III was unable to engage the Bulgarian army because his troops were outnumbered. He offered Michael Shishman a duel to solve the conflict. The Bulgarian emperor answered with the words cited by John Kantakouzenos:[12][13]

Stupid would be the blacksmith who instead of taking the hot iron with pincers takes it with his hands. He himself would be ridiculed by the Bulgarians if he risks not his large and strong army but his own body.

The Byzantine emperor was said to have been infuriated with the answer and the fact that he was outsmarted. However, Michael III who was informed of the conflict between Andronikos III and Andronikos II hinted him that he could help Andronikos III against his grandfather in case of war and returned to Bulgaria promising that soon he would begin negotiations.[12]

On a council held in Constantinople on the relations with Bulgaria it was decided that the two countries should begin negotiations despite the calls for punishing the Bulgarians for the invasion. Michael Shishman divorced his wife Anna Neda and married Theodora Palaiologina, the 35-year-old widow of emperor Theodore Svetoslav.[14] The exact reasons for that act are unclear. Many historians suggest that the deterioration of the Bulgarian-Serbian relations was rooted in the Serbian penetration in Macedonia.[15][16] The marriage cemented the peace treaty with the Byzantine Empire but the need for an ally against the Serbs made Michael Shishman prone to make concessions. It was decided that the border should follow the Philippopolis-Chernomen-Sozopol line.[15] The agreement was finally signed in the autumn of 1324 and Michael Shishman spent the next several years at peace with his neighbors.[15][17]

In 1327 Michael Shishman became involved in the renewed civil war in the Byzantine Empire, taking the side of his brother-in-law Andronikos III, while his grandfather and rival Andronikos II obtained the support of the Serbian king. Andronikos III and Michael Shishman met at Chernomen (according to Nicephorus Gregoras at Dimotika)[18] and concluded an aggressive alliance against Serbia. The Byzantine emperor promised to Bulgaria territory with several towns and large amount of money if he would become a sole emperor.[19] Based on that alliance, Andronikos III gained control of Macedonia but his success made Michael Shishman, who aimed at a prolonged conflict within the Byzantine Empire, enter into negotiations with Andronikos II, offering military support in exchange for money and the cession of some border lands.[20] The Bulgarian ruler sent a detachment of 3,000 cavalry, commanded by Ivan the Russian, from Yambol to guard the Imperial Palace in Constantinople and Andronikos II but his intentions were to capture the old emperor and the city.[21][22] Forewarned by his grandson, Andronikos II prudently kept the Bulgarians away from the capital and his person. When Michael Shishman understood that his plans were revealed he sent Ivan a letter with a single feather to retreat which meant that the orders had to be promptly executed.[23]

Following the victory of Andronikos III over his grandfather, Michael Shishman attempted to gain some lands by force. He invaded Thrace in June 1328 and pillaged the vicinities of Viza but retreated before the advance of Andronikos III.[24] Another showdown in front of Adrianople 60 days later ended without battle and with the renewal of the peace treaty in October 1328, after which Michael Shishman returned to his country, but not before securing a large payoff.[25] In return, the Bulgarians gave back the fortress of Bukelon which they had taken during the initial stages of the campaign.[26] In the beginning of the next year the Bulgarian emperor requested a personal meeting with his Byzantine counterpart to negotiate a definitive treaty and joint military operations against the growing power of Serbia.[1] In the locality known as Krimni between Sozopol and Anchialus the two signed "lasting peace and eternal alliance".[24]

^ a: The common usage Michael Shishman is technically inaccurate, as it consists of the name Michael followed by the patronymic Shishman, i.e., Michael [the son of] Shishman. Contemporary Bulgarian and Byzantine sources show that the emperor reigned under the name Michael Asen: Mladjov 2015: 276-277. He is also known among historians as Michael III Shishman or Michael III Shishman Asen.
^ b: Traianopolis was a town near modern Feres, situated at 2 kilometres (1.2 mi) of the Maritsa river in Western Thrace.[41]
^ c: The numbers designate which wife each child was born to.

• Андреев (Andreev), Йордан (Jordan); Лалков (Lalkov), Милчо (Milcho) (1996). Българските ханове и царе [The Bulgarian Khans and Tsars] (in Bulgarian). Велико Търново (Veliko Tarnovo): Абагар (Abagar). ISBN 954-427-216-X.
• Вожилов (Bozhilov), Иван (Ivan); Гюзелев (Gyuzelev), Васил (Vasil) (1999). История на средновековна България VII-XIV век [History of Medieval Bulgaria 7th–14th Centuries] (in Bulgarian). София (Sofia): Анубис (Anubis). ISBN 954-426-204-0.
• Fine, J. (1987). The Late Medieval Balkans, A Critical Survey from the Late Twelfth Century to the Ottoman Conquest. The University of Michigan Press. ISBN 0-472-10079-3.
• Колектив (Collective) (1980). "XIX. Йоан Кантакузин (XIX. John Kantakouzenos)". Гръцки извори за българската история (ГИБИ), том X (Greek Sources for Bulgarian History (GIBI), volume X) (in Bulgarian and Greek). София (Sofia): Издателство на БАН (Bulgarian Academy of Sciences Press).
• Gregory, T. (2005). A History of Byzantium. Blackwell Publishing. ISBN 0-631-23513-2.
• Jireček, Konstantin (1977). Geschichte der Bulgaren (in German). Frankfurt am Main: Textor Verlag. ISBN 978-3-938402-11-5.
• Kazhdan, A.; collective (1991). "Volume II". The Oxford Dictionary of Byzantium. New York, Oxford: Oxford University Press. ISBN 0-19-504652-8.
• Mladjov, I., "Monarchs' Names and Numbering in the Second Bulgarian State," Studia Ceranea 5 (2015) 267-310 online.
• Павлов (Pavlov), Пламен (Plamen) (2005). "Руски "бродници", политически политически бегълци и военачалници през XII-XIV век (Russian "Vagrands", Political Refugees and Commanders during the 12th–14th Centuries)". Бунтари и авантюристи в средновековна България (Rebels and Adventurers in Medieval Bulgaria) (in Bulgarian). Varna: LiterNet. ISBN 954-304-152-0.