[2][3] In the first two decades of the 15th century, following the death of its first king Tvrtko I, the Kingdom of Bosnia began developing into a less-centralized state with three powerful noble families Pavlović, Vukčić, and Hranić.
Probably through Ottoman mediation, two magnates started negotiations, which lasted until June 1439, ending in peace between the two houses and the renewal of family ties; Radislav remarried Stjepan's sister.
They warned their Bosnian neighbors friendship bought for money is neither firm nor permanent, and indicated the fate of other regional lords, Serbs, Byzantines, Albanians, who had perished or suffered as a result of their own discord.
[28] At the beginning of July 1439, Murad II set out to conquer Bosnia's eastern neighbor the Serbian despotate, and was joined by his Bosnian vassal Stjepan Vukčić Kosača, who participated in a devastation of Serb realm.
A lengthy succession crisis broke out in Hungary, which prompted Bosnian Duke Stjepan Vukčić and King Tvrtko II to conquer the lands of Croatian lord Matija Talovac.
[16] Sensing problems, Ragusans dispatched envoys to Stjepan's court with instructions to appeal to him by arguing he is now "the most powerful and most wise Bosnian lord" who must preserve "the peace and unity in the country"; if he does, it will bring him "glory throughout the world".
On 15 February 1444, Stjepan signed a treaty with the King of Aragon and Naples, becoming his vassal in exchange for Alfonso's help against his enemies—King Thomas, Duke Ivaniš Pavlović and the Republic of Venice.
As Stjepan Vukčić was a staunch supporter of and adherent to the Bosnian Church, Thomas's conversion to Roman Catholicism, probably by the time of negotiations to marry the duke's daughter Catherine between 1445 and 1446, were another obstacle in their relations.
Ottoman retaliation against the king allowed Stjepan to take back the lost possessions in the Neretva Valley, and place Thomas' allies the Radivojević noble family under his authority again.
[40] A rapprochement with Stjepan via marriage with his daughter Catherine of Bosnia (Katarina), was probably mooted by 1445,[41] when Thomas sought improved relations with the Holy See to be cleared of the "stain of illegitimacy" and to receive an annulment of his union with commoner and krstjanka, Vojača.
[55] The reason behind infighting can be found in a writing by the Italian chronicler Gaspare Broglio Tartaglia da Lavello, who says that Herzeg's envoys brought from Florence a young Sienese girl, intending to present her to his son, Vladislav.
[58] King came with his vassal Petar Vojsalić and a military contingent in mid-April, when allied forces including Vladislav, Vlatkovićs and all the other petty Hum's nobility came together against Herceg and his younger son Vlatko.
[59] The alliance was very successful, especially because Hum's general population was extremely dissatisfied with Stjepan's rule, the king and despot were in agreement and the Porte, on huge Herceg disadvantage, was neutral;[60] only Venice remained friend with him during the war,[61] and he had his local vassals.
[68] With some doubt over the exact date and place, Herceg Stjepan eventually forgave his eldest son, his wife, and Hum's nobility for rebelling against him, and everything was sealed with a treaty in a ceremony held in Pišče [sh] on the Piva, on the road to the Sokol Fortress, between 1 and 5 June, with the confirmation and vouching by the djed of the Bosnian Church and its 12 clerics, called strojniks, and led by gost Radin, who served as witnesses.
[69][70] It was also stipulated that the Herceg must not take any action against dukes Ivaniš Vlatković and Sladoje Semković, and knezs Đurađ Ratković and Vukašin Sanković, nor any of the nobles who were not part of the family's immediate circle, until the suspicions were first checked by the djed of the Bosnian church, twelve strojniks, among which a place was reserved for Radin Gost.
[73] Herceg Stjepan refrained from claiming the Bosnian crown for his adolescent grandson Sigismund, Catherine's son and Stephen Tomašević's half-brother, probably realizing Bosnia needed a strong, mature monarch in a time of peril.
The Ottomans threatened the territory of Bosnia while attacks against the kingdom's southern edges by Pavao Špirančić, Ban of Croatia and Dalmatia, between September 1461 and the beginning of 1462,[77] resulted in the capture of one Bosnian border town.
[90][91] Attempts to restore the Bosnian kingdom, mostly under the auspices of external powers, primarily Hungarians whom historiography sees as major culprit for its fall,[92] lasted until the beginning of the 16th century.
[94] Around the same time, late 1473 to early 1474, his younger brother Stjepan departed for Istanbul,[95] where he converted to Islam as Ahmed Pasha Hercegović, after which he would hold various top positions in his 40-year career, including the highest function in the Ottoman navy.
It seems this fact must have left a very strong impression and was constantly on the duke Stjepan's mind, because he at first tried to acquire this exact same title, Herceg of Split, from King Alfons V.[101] This kind of internal Bosnian dynamic was met with little or no interest, although in medieval Europe, a strict hierarchical order did not allow such "usurpation" to pass unnoticed.
The Holy See in the Vatican treated Stjepan as a Catholic while simultaneously the Ecumenical Patriarchate of Constantinople considered him Orthodox,[107] but they also laid claims of him being heretic and belonging to the Bosnian Church–the pope IV explicitly accused Herceg of such transgression.
[116] When Herceg Stjepan agreed the peace with his eldest son, his wife, and Hum's nobility after they rebelled against him, the treaty was sealed in a ceremony in front of djed of the Bosnian Church and its 12 clerics, called strojniks headed by gost Radin, who served as witnesses.
[69][70] By the same treaty it was also stipulated that the Herceg must not take any action against any of the nobles outside the family's immediate circle until the suspicions were first checked by the djed of the Bosnian Church, twelve strojniks, among whom a place was again reserved for Radin Gost.
[121] In 1964, Ćirković published his historical biography Herceg Stefan Vukčić-Kosača i njegovo doba, using his predecessors, and in particular the research of Ilarion Ruvarac, Jakov Lukarević, Lajos Thallóczy, Aleksa Ivić, Mihajlo Dinić, and Vladimir Ćorović.
[121] According to Sima Ćirković, assessing information about Stjepan Vukčić Kosača's personality from contemporary documents is unhelpful because they were created under specific circumstances to satisfy political and economic needs, so they are often idiosyncratic and biased.
He paraphrased Thallóczy, calling Stjepan "cunning, capricious, brutal and a coward, a friend of wine and women, unusually reckless in choosing means, but with a highly developed ability to notice a change in the political circumstance".
[123] According to Vladimir Ćorović, Stjepan had "a strong will and a bad temper", "had strength and skills, but no morale", and saying "since coming to power, he was surprising the world with his ruthlessness, by which he provoked conflicts not only with his neighbors but even in his own family".
[123] The medieval town Novi was founded as a fortress in a small fishing village in 1382 by the first King of Bosnia Tvrtko I Kotromanić, and was originally named Sveti Stefan (Saint Stephen).
[98][33] This is a superficial understanding because the appearance of the name Herzegovina, which is recorded in 1 February 1454 in a letter written by the Ottoman commander Esebeg from Skopje,[98] cannot be attributed to Stjepan alone, and his title was not of decisive importance.
Also, Stjepan did not establish this province as a feudal and political unit of the Bosnian state; that honor befell Grand Duke of Bosnia Vlatko Vuković, who received it from King Tvrtko I; Sandalj Hranić expanded it and reaffirmed the Kosača family's supremacy.