History of Syldavia from the 14th to 16th century

In the late 14^th century, Syldavia was caught in a vice between the Venetians who continued to expand into the Balkans from the northwest and the Ottomans who began to press into the Balkans from the southeast.  Moving north from the ruins of Byzantium, the Ottomans overwhelmed Bulgaria in the 1390’s. When Borduria fell soon afterwards, Syldavia suddenly found the Ottomans on their northern and eastern borders. The whole region fell into a chaotic and fearful reactive stance for the next century as the Ottomans pushed incrementally to the north.  Syldavia reinforced its frontier forts and waited grimly. In order to stave off pressure on its vulnerable trading fleet from both the Venetians and the Ottomans, the independent city state of Dbrnouk chose to become a nominal tributary (on very liberal terms) of the Ottomans in 1469.  They stayed assiduously out of conflict as far as possible and free of any real Ottoman occupation.  The Ottomans, preferring to tax Dbrnouk’s trade rather choking it off by making the city into an isolated theatre of war with Venice, left the city largely alone.

Dbrnouk in the 17th century

Syldavia’s mountainous border and its marginal value to the Ottomans given their much greater interest in richer lands further to the north (notably the Danube corridor and the Hungarian plain) saved Syldavia in the short term.  A combination of stubborn military resistance aided by troops and fortifications paid for and built by the Venetians, diplomacy and the continued resistance of Albania further prolonged Syldavia’s semi-autonomy.  Nevertheless, through incessant raids and episodic small campaigns, Syldavia gradually lost most of its inland territory to the Ottomans and Borduria by 1430.  In between these campaigns, the desperately weakened, King Karel and his successor King Grygor II pledged vassalage alternately to the Venetians and the Ottomans and a few times to both at once, in order to forestall outright conquest.  Under unremitting pressure, however, (especially after the fall of Albania in 1468), Syldavia was finally overrun in 1494 and annexed to the Ottoman Pashaluk of Borduria.  At the 11^th hour, with the final Ottoman advance bearing down, the ageing King Grygor knew that Syldavia’s time had run out.  He smuggled his family out of Syldavia with his most loyal retainers and treasure.  The promise of a possible future for the dynasty secured, Grygor led a final raid against the Ottomans in the Wladir River valley near Rivajow, where he was captured.  In shameful captivity, Grygor was executed, his body buried in an unknown place.  The Almazout family fled in exile to Italy and later to Vienna, where they were received with sympathy by the Habsburg court. The family converted to Roman Catholicism at this time, a move noted both in Vienna and Rome.  The young heir in-exile, Alexander I, become a notable officer of the Knights of Malta and a scourge of the Ottomans at sea, many of whose corsairs in the Adriatic were now based at Cattaro.  Many Syldavians became exiles as well as refugees moved to Croatia and some to Italy, Austria and further afield.  There is even mention of a troop of mountaineers from Zympathia in the employ of far-off Tradgardland. 

The Ottoman occupation was soon contested.  The Venetians organised and armed displaced Syldavian refugees and allied with the restive clans still residing in the coastal provinces in a long struggle to push the Ottoman frontier back to the east.  The conspicuous service of Alexander I with the Knights of Malta served him well, as he (now a man in his prime) was given command of a force of Syldavian exiles, Knights and Austrian volunteers with which he re-took the town of Douma in 1516 and then lead a night attack on a key fortification in the harbour at Cattaro in 1517.  The port was opened to the Venetian ships and the Bordurian garrison capitulated once the Venetian troops made land.  In 1518, the presence of Alexander in Syldavia at the head of an armed force incited a popular uprising (much as happened in 1204) and the bulk of the provinces of Hum, Travunia and Zeta all fell relatively rapidly to the Veneto-Syldavian forces.  Dbrnouk became a vassal of Venice as well. Venice, facing the obvious political situation caused by the uprising inspired by Alexander and considerable pressure from Vienna and the Vatican in support of him, reluctantly accepted the reinstatement of the Almazoutian dynasty as kings of the reclaimed territories. 

Venetian-built fortifications at Cattaro, modified in the 17th century 

Venetian-built fortifications protecting the landward approaches to Cattaro

The price of Venetian protection of the Almazout dynasty included a pact guaranteeing Syldavia’s quasi-colonial status and other such niceties as preferential Venetian trade rights and bases in Cattaro and Douma.  Several generations of Syldavian kings preferred their tributary status to extinction and happily lived with this deal.  Quite naturally, Syldavian society and its military followed Venetian trends during this time.  While the Venetians oversaw the reconstruction of the coastal territories, including building imposing fortifications and new port facilities, the military situation was deadlocked in the interior.  The Ottoman (Bordurian) – Syldavian border fluctuated frequently along the mountains separating Wladruja from Hum and Travunia at this time; occasional minor gains in territory were balanced by minor losses.  This stalemate lasted well into the 17^th century. 

King Alexander I, wearing habit of the Knights of Malta

A modern view of the town of Cattaro