Chapter 1: A Thunder In the East
Author’s Note: With absolutely no thanks to my University for making my life rough, and pulling me away from my passion for Alternate History, I return to timeline writing! I’ve always wanted to write an alternate history on a different rise of the Ottomans that leads to a new path in history and I actually began writing this in May 2022. I’ve finally completed my research on the Early Ottomans (which was helpful for my thesis as well!) and well here is that project. Hope everyone enjoys it!
By the time of the Battle of Kosovo in 1389 AD, Europe had been too late. The Ottoman advance into the Balkans could have been prevented by the Serbs or the Bulgarians alongside the Byzantines had they taken swift action in the 1340s and 1350s, however, a series of political and military feuds left the Ottomans firmly established on the western shores of the Bosporus straits. The Byzantines who became enveloped by the Ottomans after their capture of Adrianople reached out to various European powers for aid against the Turcomans. Any potential aid always came at the price of reuniting the Catholic and Orthodox Churches, a point of contention that was extremely uncomfortable for any Byzantine Emperor to make promises for.
Lala Şahin Pasha
The man who led 800 Ottoman Troops to Victory against 30,000 - 70,000 Serbs
Nevertheless, the Conquest of Adrianople opened up a large amount of pressure on the Serbs, who allied themselves with the Byzantines. In 1371 a powerful Serbian expedition of 30,000 – 70,000 troops against the Ottomans met with disaster at the hand of a simple band of 800 Ottoman troops at the Battle of Maritsa. The Battle of Maritsa not only confirmed the primacy of the Ottoman military machine, but it also opened up the remnants of Thrace and southern Macedonia to Ottoman conquests and brought the Bulgarians and several Serbian boyars into the Ottoman world as tributaries to the Ottoman Sultan. Despite this disastrous defeat, however, Serbian lords and boyars rallied around the leadership of Prince Lazar Hrebeljanovic of Moravian Serbia and managed to defeat the Ottomans in 1386 at the Battle of Plocnik and in 1388 at the Battle of Bileca, threatening the Ottoman conquests in the Balkans.
In 1389, the situation became intolerable for Sultan Murad I, and he invaded Moravian Serbia with the sole intention of bringing the Serbs to heel once more. Murad I planned the invasion of Moravian Serbia in 1389 with the grand intention of not only annexing Moravian Serbia, but pushing into Bosnia as well to punish the Bosnian lords who were aiding the Serbs against the Ottomans. On 15 June 1389, a large Ottoman army of around 30,000 men was confronted by Prince Lazar who led an army 20,000 strong in Kosovo near the town of Prishtina. This grand battle lasted for 8 hours, and by the end of the fighting, though bloodied, the Ottomans came out victorious during the battle. But Sultan Murad I did not live to celebrate his victory against the Serbs as one of the Serbian commanders tricked Murad I into thinking he was defecting before stabbing Murad I to death. Though the Ottomans had come out victorious, they were now leaderless.
A romanticized painting of the Battle of Kosovo 1389
Had the battle played out differently, all of history could have been changed. Sehzade Bayezid, the eldest son of Sultan Murad I was grievously wounded during the fighting at the Battle of Kosovo and was on his deathbed alongside his father. Sehzade Bayezid would die eight days after the Battle of Kosovo from the wounds he received during the fighting. [1]. Sehzade Yakub, who led the left flank of the Ottoman Army during the Battle of Kosovo was called into the royal tents and was immediately proclaimed Sultan Yakub I of the Ottoman Empire with the agreement of the prominent Pashas who had participated during the battle.
Sultan Yakub I of the Ottomans
Initially, the Battle of Kosovo was interpreted as a great Christian victory as only the death of Sultan Murad I filtered out of Serbia into Christendom. King Charles VI of France went so far as to order a grand service of thanksgiving at Notre Dame in the name of Prince Lazar of Serbia. But soon enough the disastrous consequences of the Battle of Kosovo quickly became known as survivors of the battle fled into Bosnia and Hungary from where the truth sped. Where the Ottomans had lost their Sultan, the Serbs had been entirely annihilated as a military force to counter the Ottomans at any length.
After his formal announcement as Sultan, Yakub I dealt with the aftermath of the battle. Where his elder brother had been too hotheaded, Yakub I was both militarily and administratively competent as well as being a known benevolent figure. His benevolence, however, did not extend to the Serbian knight who killed his father, who was executed immediately under Yakub I’s orders. Yakub I also had to deal with Prince Lazar. Prince Lazar was taken to Adrianople where he lived the remainder of his 14 years under tight house arrest. Though Yakub I respected Lazar and his military prowess, Yakub I could never come to see the Serbian prince as anything other than being responsible for his beloved father’s death. Yakub I spared Lazar’s family, however. The young 12-year-old Stefan Lazarevic who was now heir to Moravian Serbia was allowed to live under the condition that he be kept hostage in Adrianople for 5 years until his majority when he would be allowed to return to Moravian Serbia to rule as an Ottoman vassal. Until then the wife of Prince Lazar, Princess Milica was expected to handle Serbian affairs as Regent. In return for the extraction of promises of the safety of both her son and husband, Princess Milica agreed to rule as Regent in Serbia under Ottoman suzerainty.
Princess Milica would soon with Ottoman support invade and annex the realm of the Brankovic Dynasty back into Moravian Serbia, partitioning it between her nation and the Ottomans. The Albanian Lords who had taken part in the Battle of Kosovo were also attacked with the Principality of Muzaka on the Adriatic Coast being invaded by Gazi Evrenos Bey with 9,000 soldiers. Though the mountains of this hostile Albanian region remained outside of Ottoman authority, the major cities of the Principality alongside most of its routes fell to Gazi Evrenos Bey and his vengeful troops, thus expanding the Ottoman Empire towards the Adriatic Sea for the first time. Berat – the capital of the then Principality of Muzaka – became the main Ottoman base in Albania for decades into the future. There was of course, however, the problem of Tsar Ivan Shishman of Bulgaria, who remained slippery with his dealings with the Ottomans. With the Ottomans victorious over Kosovo, the Bulgarian Tsar had switched sides once again and reaffirmed his ‘old’ loyalty to the Ottoman Sultan, graciously bending down to Sultan Yakub I when the two met with one another as Yakub I traveled back towards Adrianople after Kosovo. Though wary of the Bulgarian Tsar, Yakub I decided to remain at peace with Bulgaria and accepted Tsar Ivan Shishman’s indirect offer of continued peace.
Coat of Arms of Muzaka
Immediately upon his return to Adrianople, Yakub I was confronted by a large Anti-Ottoman Coalition formed by the remaining Turkish beys of Anatolia led by his brother-in-law Alaeddin Bey, Emir of the Karamanids, who was wed to his sister Nefise Sultan in 1378 a decade prior. Though dynastic marriage was often used during this time period to end the conflict between two powers, the marriage of Nefise Sultan to Alaeddin Bey did nothing to stop the growing enmity between the Karamanids and the Ottomans. Pasha Yigit Bey was dispatched with 14,000 troops to hold off Alaeddin Bey until Yakub I could gain the allegiance of the Uch Bey Lords of the Ottoman Imperial apparatus who were all traveling to Adrianople to reaffirm their loyalty to the new Sultan. Yakub I managed to gain the support of most of the Uch Beys and Grand Vizier Candarli Ali Pasha then raised the issue of succession.
Yakub I was already 30 years of age in 1389, and he had no children nor a consort. A deeply pious man, he had taken no concubine either, despite the urging of his father Murad I. Yakub I could not go head deep into battle without having first secured the succession for there was always the chance that he would die in combat like his father and leave the fate of the nascent Sultan hanging in the balance. According to the vague succession laws that governed the Ottoman Empire during this time, it would be Alaeddin Bey and Nefise Sultan’s son, Sehzade Mehmed of the Karamanids who would be set to inherit the Ottoman Empire in case of Yakub I having no heir. This was a prospect that the governing Beys and Pashas of the Ottoman Empire wanted to avoid at all costs.
Yakub I in the end decided to ensure the loyalty of his slippery Bulgarian vassal and ensure the succession at the same time. Tsar Ivan Shishman of Bulgaria, who was now ruling over an impoverished realm could not refuse the offer of 30,000 Ottoman ducats as a bride price and a guarantee of no raiding of his realm. Tsar Ivan Shishman betrothed his daughter Princess Desislava of Bulgaria to Sultan Yakub I. Desislava left Tarnovo on 13 October 1389 and reached Adrianople two weeks later on the 27th, where the Bulgarian Princess was wed to Yakub I. Thereafter in Ottoman historiography she became known as Desislava Hatun [2]. Like many Ottoman wives of the past who were of Christian background, she was allowed to retain her faith in Eastern Orthodoxy by Yakub I. Though Yakub I and Desislava Hatun did not get along with one another during the first few years of their marriage, the two managed to consummate their marriage a few times afterward and Yakub I decreed that any child born of Desislava Hatun would be the heir of Ottoman realm should he die on the battlefield. This was the first time in Ottoman history a definitive decree was passed regarding succession and paved the way for formalizing succession traditions in the future.
Desislava Hatun
With his succession tenuously secured, an Ottoman force gathered in Adrianople as Yakub I decided to reinforce Pasha Yigit Bey who had been pushed out of Angora by Alaeddin Bey and his Karamanid host. On January 26, 1390, Sultan Yakub I crossed the Hellespont to claim his place in history.
All the universe, one mighty sign, is shown;
God hath myriads of creative acts unknown;
None hath seen them, of the races jinn and men;
None hath news brought from that realm far off from ken.
Never shall thy mind or reason reach that strand,
Nor can tongue the King’s name utter of that land.
Since ‘tis his each nothingness with life to vest,
Trouble is there ne’er at all to his behest.
Eighteen thousand worlds, from end to end,
Do not with him one atom’s worth transcend.
-Divan of the Lover
Divan of Sultan Murad I
Chapter 1
A Thunder in The East
God hath myriads of creative acts unknown;
None hath seen them, of the races jinn and men;
None hath news brought from that realm far off from ken.
Never shall thy mind or reason reach that strand,
Nor can tongue the King’s name utter of that land.
Since ‘tis his each nothingness with life to vest,
Trouble is there ne’er at all to his behest.
Eighteen thousand worlds, from end to end,
Do not with him one atom’s worth transcend.
-Divan of the Lover
Divan of Sultan Murad I
Chapter 1
A Thunder in The East
By the time of the Battle of Kosovo in 1389 AD, Europe had been too late. The Ottoman advance into the Balkans could have been prevented by the Serbs or the Bulgarians alongside the Byzantines had they taken swift action in the 1340s and 1350s, however, a series of political and military feuds left the Ottomans firmly established on the western shores of the Bosporus straits. The Byzantines who became enveloped by the Ottomans after their capture of Adrianople reached out to various European powers for aid against the Turcomans. Any potential aid always came at the price of reuniting the Catholic and Orthodox Churches, a point of contention that was extremely uncomfortable for any Byzantine Emperor to make promises for.
Lala Şahin Pasha
The man who led 800 Ottoman Troops to Victory against 30,000 - 70,000 Serbs
Nevertheless, the Conquest of Adrianople opened up a large amount of pressure on the Serbs, who allied themselves with the Byzantines. In 1371 a powerful Serbian expedition of 30,000 – 70,000 troops against the Ottomans met with disaster at the hand of a simple band of 800 Ottoman troops at the Battle of Maritsa. The Battle of Maritsa not only confirmed the primacy of the Ottoman military machine, but it also opened up the remnants of Thrace and southern Macedonia to Ottoman conquests and brought the Bulgarians and several Serbian boyars into the Ottoman world as tributaries to the Ottoman Sultan. Despite this disastrous defeat, however, Serbian lords and boyars rallied around the leadership of Prince Lazar Hrebeljanovic of Moravian Serbia and managed to defeat the Ottomans in 1386 at the Battle of Plocnik and in 1388 at the Battle of Bileca, threatening the Ottoman conquests in the Balkans.
In 1389, the situation became intolerable for Sultan Murad I, and he invaded Moravian Serbia with the sole intention of bringing the Serbs to heel once more. Murad I planned the invasion of Moravian Serbia in 1389 with the grand intention of not only annexing Moravian Serbia, but pushing into Bosnia as well to punish the Bosnian lords who were aiding the Serbs against the Ottomans. On 15 June 1389, a large Ottoman army of around 30,000 men was confronted by Prince Lazar who led an army 20,000 strong in Kosovo near the town of Prishtina. This grand battle lasted for 8 hours, and by the end of the fighting, though bloodied, the Ottomans came out victorious during the battle. But Sultan Murad I did not live to celebrate his victory against the Serbs as one of the Serbian commanders tricked Murad I into thinking he was defecting before stabbing Murad I to death. Though the Ottomans had come out victorious, they were now leaderless.

A romanticized painting of the Battle of Kosovo 1389
Had the battle played out differently, all of history could have been changed. Sehzade Bayezid, the eldest son of Sultan Murad I was grievously wounded during the fighting at the Battle of Kosovo and was on his deathbed alongside his father. Sehzade Bayezid would die eight days after the Battle of Kosovo from the wounds he received during the fighting. [1]. Sehzade Yakub, who led the left flank of the Ottoman Army during the Battle of Kosovo was called into the royal tents and was immediately proclaimed Sultan Yakub I of the Ottoman Empire with the agreement of the prominent Pashas who had participated during the battle.
Sultan Yakub I of the Ottomans
Initially, the Battle of Kosovo was interpreted as a great Christian victory as only the death of Sultan Murad I filtered out of Serbia into Christendom. King Charles VI of France went so far as to order a grand service of thanksgiving at Notre Dame in the name of Prince Lazar of Serbia. But soon enough the disastrous consequences of the Battle of Kosovo quickly became known as survivors of the battle fled into Bosnia and Hungary from where the truth sped. Where the Ottomans had lost their Sultan, the Serbs had been entirely annihilated as a military force to counter the Ottomans at any length.
After his formal announcement as Sultan, Yakub I dealt with the aftermath of the battle. Where his elder brother had been too hotheaded, Yakub I was both militarily and administratively competent as well as being a known benevolent figure. His benevolence, however, did not extend to the Serbian knight who killed his father, who was executed immediately under Yakub I’s orders. Yakub I also had to deal with Prince Lazar. Prince Lazar was taken to Adrianople where he lived the remainder of his 14 years under tight house arrest. Though Yakub I respected Lazar and his military prowess, Yakub I could never come to see the Serbian prince as anything other than being responsible for his beloved father’s death. Yakub I spared Lazar’s family, however. The young 12-year-old Stefan Lazarevic who was now heir to Moravian Serbia was allowed to live under the condition that he be kept hostage in Adrianople for 5 years until his majority when he would be allowed to return to Moravian Serbia to rule as an Ottoman vassal. Until then the wife of Prince Lazar, Princess Milica was expected to handle Serbian affairs as Regent. In return for the extraction of promises of the safety of both her son and husband, Princess Milica agreed to rule as Regent in Serbia under Ottoman suzerainty.
Princess Milica would soon with Ottoman support invade and annex the realm of the Brankovic Dynasty back into Moravian Serbia, partitioning it between her nation and the Ottomans. The Albanian Lords who had taken part in the Battle of Kosovo were also attacked with the Principality of Muzaka on the Adriatic Coast being invaded by Gazi Evrenos Bey with 9,000 soldiers. Though the mountains of this hostile Albanian region remained outside of Ottoman authority, the major cities of the Principality alongside most of its routes fell to Gazi Evrenos Bey and his vengeful troops, thus expanding the Ottoman Empire towards the Adriatic Sea for the first time. Berat – the capital of the then Principality of Muzaka – became the main Ottoman base in Albania for decades into the future. There was of course, however, the problem of Tsar Ivan Shishman of Bulgaria, who remained slippery with his dealings with the Ottomans. With the Ottomans victorious over Kosovo, the Bulgarian Tsar had switched sides once again and reaffirmed his ‘old’ loyalty to the Ottoman Sultan, graciously bending down to Sultan Yakub I when the two met with one another as Yakub I traveled back towards Adrianople after Kosovo. Though wary of the Bulgarian Tsar, Yakub I decided to remain at peace with Bulgaria and accepted Tsar Ivan Shishman’s indirect offer of continued peace.
Coat of Arms of Muzaka
Immediately upon his return to Adrianople, Yakub I was confronted by a large Anti-Ottoman Coalition formed by the remaining Turkish beys of Anatolia led by his brother-in-law Alaeddin Bey, Emir of the Karamanids, who was wed to his sister Nefise Sultan in 1378 a decade prior. Though dynastic marriage was often used during this time period to end the conflict between two powers, the marriage of Nefise Sultan to Alaeddin Bey did nothing to stop the growing enmity between the Karamanids and the Ottomans. Pasha Yigit Bey was dispatched with 14,000 troops to hold off Alaeddin Bey until Yakub I could gain the allegiance of the Uch Bey Lords of the Ottoman Imperial apparatus who were all traveling to Adrianople to reaffirm their loyalty to the new Sultan. Yakub I managed to gain the support of most of the Uch Beys and Grand Vizier Candarli Ali Pasha then raised the issue of succession.
Yakub I was already 30 years of age in 1389, and he had no children nor a consort. A deeply pious man, he had taken no concubine either, despite the urging of his father Murad I. Yakub I could not go head deep into battle without having first secured the succession for there was always the chance that he would die in combat like his father and leave the fate of the nascent Sultan hanging in the balance. According to the vague succession laws that governed the Ottoman Empire during this time, it would be Alaeddin Bey and Nefise Sultan’s son, Sehzade Mehmed of the Karamanids who would be set to inherit the Ottoman Empire in case of Yakub I having no heir. This was a prospect that the governing Beys and Pashas of the Ottoman Empire wanted to avoid at all costs.
Yakub I in the end decided to ensure the loyalty of his slippery Bulgarian vassal and ensure the succession at the same time. Tsar Ivan Shishman of Bulgaria, who was now ruling over an impoverished realm could not refuse the offer of 30,000 Ottoman ducats as a bride price and a guarantee of no raiding of his realm. Tsar Ivan Shishman betrothed his daughter Princess Desislava of Bulgaria to Sultan Yakub I. Desislava left Tarnovo on 13 October 1389 and reached Adrianople two weeks later on the 27th, where the Bulgarian Princess was wed to Yakub I. Thereafter in Ottoman historiography she became known as Desislava Hatun [2]. Like many Ottoman wives of the past who were of Christian background, she was allowed to retain her faith in Eastern Orthodoxy by Yakub I. Though Yakub I and Desislava Hatun did not get along with one another during the first few years of their marriage, the two managed to consummate their marriage a few times afterward and Yakub I decreed that any child born of Desislava Hatun would be the heir of Ottoman realm should he die on the battlefield. This was the first time in Ottoman history a definitive decree was passed regarding succession and paved the way for formalizing succession traditions in the future.
Desislava Hatun
With his succession tenuously secured, an Ottoman force gathered in Adrianople as Yakub I decided to reinforce Pasha Yigit Bey who had been pushed out of Angora by Alaeddin Bey and his Karamanid host. On January 26, 1390, Sultan Yakub I crossed the Hellespont to claim his place in history.
- Chasing the Horizon – Charles Blanchet, Parisian Historical Publishing House, 2019 AD
Footnotes:-
[1] – According to Ottoman Chronicles, a Serbian raid on Bayezid’s flank got really close for comfort to Bayezid during Kosovo in 1389. The PoD is just that, the raid gets close enough.
[2] – Hatun is an honorific in Turco-Mongol etymology roughly translating to ‘Noble Lady’ or ‘Great Mother’ depending on the linguist you’re using.
Summary:-
1389: The Battle of Kosovo ends in Ottoman victory. Murad I and Sehzade Bayezid die in the field of combat. Sehzade Yakub becomes Sultan and marries Princess Desislava of Bulgaria.