Amadeus of Savoy's Crusade

In the mid-14th century, the Byzantine state found itself in a complex political situation, with the main leader of its internal and external policy being John Kantakouzenos. He faced the challenge posed by the Bulgarian noble Dobrotitsa, who ruled the city of Midia (present-day Midia, Bulgaria) as an independent ruler and began carrying out devastating raids against the surrounding towns. These actions by Dobrotitsa represented a serious threat to the stability of the region and to the authority of the Constantinopolitan government, which necessitated a decisive response.

In response to these provocations, Kantakouzenos undertook a military campaign against Dobrotitsa with the aim of forcing him to submit to Byzantine authority. In the summer of 1347, the forces of the Constantinopolitan government, personally led by John Kantakouzenos and Emperor John V Palaiologos, besieged Midia both by land and by sea. This coordinated siege demonstrated the seriousness of the Byzantine government's intentions to put an end to Dobrotitsa's autonomous rule and to restore its control over the region.

Despite the strong siege, Dobrotitsa decided to surrender voluntarily to his opponents, probably realizing that resistance was pointless in the face of the superior forces arrayed against him. After his surrender, Kantakouzenos treated the Bulgarian noble favorably, granting him a pronoia—a type of feudal holding that provided certain rights and income. Moreover, Kantakouzenos included Dobrotitsa among the circle of the most distinguished aristocrats, which attests to his desire to integrate the Bulgarian ruler into the Byzantine aristocracy and secure his loyalty.

Despite the temporary calm, in 1352 unrest broke out again in Byzantium, necessitating Bulgarian intervention. The Bulgarian army was sent to assist Emperor John V Palaiologos, indicating that despite previous conflicts, moments of cooperation existed between Bulgaria and Byzantium. However, after strong Turkish detachments came to Kantakouzenos's aid, the Bulgarian forces withdrew without a fight, likely due to strategic considerations to avoid becoming embroiled in a larger conflict with the growing Ottoman threat.

This Bulgarian withdrawal, however, opened the door for Ottoman incursions into Bulgarian lands. Kantakouzenos reports that the Ottomans, on their own initiative, entered Bulgaria, devastated it, and returned with plunder to their own territory. This fact highlights the increasing danger posed by the Ottomans to the region, a threat that would soon alter the political map of the Balkans.

Despite these difficulties, in 1355 an alliance was concluded between Bulgaria and Byzantium, sealed by the betrothal of Andronikos, son of the Byzantine Emperor John Palaiologos, and Keratsa, daughter of the Bulgarian Tsar Ivan Alexander. This alliance aimed to strengthen ties between the two states and to create a united front against the growing Ottoman threat.

Despite the temporary cessation of Turkish attacks and the establishment of an alliance between Bulgaria and Byzantium, relations between the two states deteriorated once again. This demonstrates how unstable and complex the political situation in the region was during this period, where alliances and conflicts changed rapidly, and external threats continued to exert a strong influence on internal politics.

In connection with the dire situation of John V and the recent Turkish successes, a decision was made to send a military expedition to support Byzantium. This expedition was entrusted to the Count of Savoy, Amadeus VI, known by the nickname "the Green Count." Amadeus was a relative of the emperor through the female line, which likely facilitated his appointment as commander of this important mission. This military action represented an attempt to stabilize the Byzantine positions and to counter the growing Ottoman threat, which was already seriously endangering the Balkan territories and Byzantium's influence in the region.

Amadeus VI of Savoy led an expeditionary detachment composed of about 2,000 fighters, who were loaded onto a total of 15 galleys. These galleys were diverse in origin – six of them were Genoese, six Venetian, and three from Marseille, reflecting the broad international character of the fleet. The majority of the fighters were condottieri, that is, mercenaries who came from various European peoples, including French, Italians, Germans, and English. The expeditionary detachment also included over 100 knights, most of whom were from Savoy, highlighting Amadeus VI’s personal involvement and the support from his vassals and subjects.

On June 20, 1366, the fleet set sail from Venice, heading towards Constantinople. After arriving there, Amadeus VI sent one galley to the mouth of the Danube River with the aim of reaching Vidin and bringing the Byzantine Emperor John V Palaiologos. However, this mission was thwarted by a severe storm, which prevented the galley from being dispatched and hindered the planned contact.

The Byzantine Empress, who was an ally of Amadeus VI, insisted that he capture important Bulgarian Black Sea fortresses. To assist in this task, she provided Amadeus with two galleys and 12,000 perpers, a significant sum intended to support the military campaign. Amadeus VI accepted this advice and decided to seize fortresses in order to compel the Bulgarian Tsar Ivan Alexander to allow the Byzantine Emperor to pass through Bulgarian lands unhindered.

Before departing from Constantinople, Amadeus VI took care to procure the necessary siege equipment, which speaks to his serious intentions to capture the fortified Bulgarian towns. At the beginning of October, the galleys left Constantinople and on October 17 reached Sozopol, where after a brief siege the fortress was taken. This success opened the way for further conquests along the Bulgarian Black Sea coast.

After the capture of Sozopol, Amadeus VI’s troops also seized the fortress of Skafida, located near the village of Dimchevo in the Burgas region. From there, a detachment set out towards the fortress of Rosokastro, situated north of the village of Rusokastro, also in the Burgas area. The first assault on Rosokastro was repelled by the defenders, but on the second attack the fortress was captured, demonstrating the attackers’ persistence and determination.

The garrison of Mesembria offered particularly strong resistance to the conquerors. The kastrichalax (castellan) of Mesembria, Kaloyan, led the defense of this medieval fortress, which stood on a rocky island. The island was 850 meters long and 300 meters wide, with an area of 25 hectares, and was connected to the mainland by a narrow causeway 400 meters in length. This natural and artificial defense made Mesembria difficult to capture, which explains the stubborn resistance of the garrison under Kaloyan’s leadership.