The Eternal State: An Ottoman Timeline

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!

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

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

[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.

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.
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!
Chapter 2 - Anatolian and Byzantine Intrigue
“Of the Turkoman Lords, there is no one greater than the Heirs of Osman.”
- John V Palaiologos

Chapter 2
Anatolian and Byzantine Intrigue

Gathering 30,000 troops under his command, Yakub I left Adrianople to secure his Anatolian holdings against the Anti-Ottoman coalition gathered by his brother-in-law. Yakub I was eager to push his holdings down south towards the Mediterranean near the shores of Rhodes, chasing after the profitable trade routes that dominated the region to fill up Ottoman coffers in the region, and after regrouping with Pasha Yigit Bey in Bursa, he pushed south towards the Germiyan Beylik, which had joined hands with the Karamanids in an anti-Ottoman bid. Antalya, which was a massive port city in southern Anatolia was a prosperous city under Karamanid control that Yakub I had his heart set for.

As 40,000 Ottoman troops burst into the scene in Germiyan territory, Bey Yakup II of Germiyan was unable to defend his realm against Sultan Yakub I. Germiyan was economically prosperous but was militarily weak, and with the bulk of the Karamanid forces occupied in central Anatolia against the Akinjis of the Ottoman forces who were distracting Alaeddin Bey, reinforcements from Konya was scarce as well. On March 12, 1390, Sultan Yakub I reached the outskirts of Aydin and asked Yakup II to surrender the city to him. Yakup II who was still confident about the ability of Alaeddin Bey to send reinforcements to him refused to consider surrender, not knowing that a small 6,000 reinforcement detachment sent to him had been defeated by the Ottomans a few days prior.


Alaeddin Bey
The leader of the Anti-Ottoman Coalition

After a week of siege, Aydin fell to a determined assault by the Janissary Corps, and Yakup II was captured and with him, the Germiyan Beylik came to an end. Yakup II was then subsequently transferred to Ipsala on the European side of the Ottoman Empire where he remained imprisoned his entire life. Aydin was annexed and Sultan Yakub I managed to march his forces towards Antalya which fell without a fight to the Ottomans. Thus under Yakub I, the Ottomans managed to conquer the entirety of the Aegean Coast of Anatolia, bringing in large swathes of territory under the rule of the Osmanid Dynasty.

Before Sultan Yakub I could make any great offensive into Karamanid territory, news arrived to him in late April 1390 about the deposition of Emperor John V of the Byzantines in favor of his rebellious grandson John VII. Recognizing John V as his vassal in his right as Emperor of the Romans, Yakub I aided John V and his son Manuel by granting several warships to the two Byzantines to regain Constantinople and conduct the August 25 Counter-Coup that led to the re-establishment of John V as Byzantine Emperor. Though Yakub I had been generous with his large amount of aid to the Byzantines, he made it clear that he expected something in return for the help. This was largely because whilst the Ottomans had become distracted by the Byzantines, Alaeddin Bey and Suleyman of Candar had managed to occupy vast swathes of what was formerly Ottoman central Anatolia.


John V

In particular, Yakub I had his eyes on Philadelphia, the last remaining Byzantine stronghold in mainland Anatolia. Manuel, diplomatically canny and shrewd left Constantinople at the behest of his father to negotiate with their titular suzerain. Fortunately for Manuel, he caught Sultan Yakub I at a good time. News had arrived from Adrianople that three weeks prior (on September 30, 1390), Desislava Hatun, one of the two wives that Yakub I would ever take in his life, had given birth to a baby girl who was named Azadeh by Desislava Hatun. Though 1390 was still before Yakub I and Desislava really began to respect each other and become affectionate with one another, Yakub I had become over the moon with the birth of his firstborn child, regardless of her gender. He had sent back most of his war loot to Adrianople in the name of his wife and daughter and had written several letters to his wife praising her. Manuel pounced on the good mood of his sovereign to ensure a lighter Ottoman demand in return for their aid in deposing John VII.

Manuel argued that Philadelphia acted as a mediator between western traders and the Ottomans and through it, the Ottomans gained much in trade revenue [1]. Though Manuel wasn’t wrong, he exaggerated the profits the Ottomans made from the city’s advanced trade network with Naples and Iberia. Fortunately for Manuel, Yakub I could see the advantage in retaining Philadelphia as a mediator for the immediate future and retracted his demand for the city. Instead, Manuel managed to convince Yakub I to remain content with 7,500 Byzantine troops to reinforce Yakub I, the yearly tribute being raised by 20%, and the expulsion of Genoese traders from Byzantine territories. Manuel also allowed himself to remain in Bursa as an honorary hostage in Bursa. Yakub I accepted this offer and this was finalized with a written agreement between the Ottoman Sultan and Byzantine Prince in Antalya on the 31st of October 1390.


The Capital of the Eastern Romans

The very next day, Yakub I left Antalya in a hurry, this time racing towards Konya to force Alaeddin Bey to fight against him in a pitched battle where the circumstances favored him. Alaeddin Bey, who had made his headquarters in Angora, began marching south with a Candari contingent to reinforce his Karamanid host to face off against the new Ottoman Sultan. It was at this time that Alaeddin Bey’s wife, Nefise Hatun, Yakub I’s sister, pleaded with her husband to stop the conflict. Nefise Hatun had become torn apart by the conflict, unable to see her beloved brother and dear husband fighting against one another. She sent a messenger to her brother Yakub I, asking for clemency and to end the conflict entirely.

According to Ottoman Chronicler Emre Ahmed Ali (c. 1360 – c.1430 AD),

……The Sultan was moved by the plight of his little sister, whom he had had a hand in raising. However, he remained steadfast in his belief that he could not be generous to a man who had broken a truce and attacked his lands. He offered his sympathies to his little sister, and promised protection to her and his nephews and nieces, but promised nothing in regards to the Karamanid Bey who had so impiously broken a noble and holy peace…….

Any chance for peace was lost with this message sent back by Yakub I. On 17 December 1390, he reached the outskirts of Konya and laid siege to the city after surrounding it. Inside, Nefise Hatun and her children were given the chance to escape to safety by Yakub I. Alaeddin Bey’s brother, Ahmed Bey, who was in command of Konya in the absence of his brother, rebuffed the offer. Nevertheless, out of concern for his sister and his nephews and nieces, he informed the military to steer clear of the central tower of Konya, where his sister and her children were holed up. Alaeddin Bey arrived north of Konya two weeks later to give battle on the Christian new year.

Sources on the Battle of Konya are surprisingly scarce, however contemporary historians, of both Christian and Islamic backgrounds agree that the Battle of Konya 1391 was a decisive Ottoman victory as the nomadic forces of Alaeddin Bey were pushed back from Konya and were forced to flee towards Angora where he could regroup with his ally, Bey Suleyman of Candar. By this point, Suleyman of Candar had already asked for aid from his brother, Isfendiyar Bey, the monarch of the Candar Beylik, having recognized that his independent military capabilities would not be enough to fend off the Ottomans. The beylik ruled by Isfendiyar Bey was a powerful beylik in its own right, boasting a military force of around 25,000 troops. With Alaeddin Bey out of Konya and any hopes of reinforcement having been lost, Konya was surrendered to the Ottomans.


Ottoman Akinjis during the Battle of Konya

Nefise Hatun and her children were escorted out of Alaeddin Mosque where she had taken refuge during the fighting. With Konya under Ottoman control, the rest of the Karamanid de-jure territories came under Ottoman administration as well. After regrouping, Yakub I pondered on his next move, for vast swathes of Ottoman territory in the north were still occupied by the Beylik of Candar and Alaeddin Bey’s remnant forces. Regrouping at Kulu, Yakub I pushed north towards Angora and reconquered the city after a year of occupation. His enemies under the command of Isfendiyar Bey had retreated beyond the northern mountains in the safety of familiar terrain near Kastamonu. The region was hostile and inhabited by Turkic tribes who were feuding with traditionally pro-Ottoman tribes and Yakub I could be certain that he would not receive any local aid.

In May 1391, his forces entered Isfendiyar Bey’s realm in an attempt to reach a final conclusion quickly. Isfendiyar Bey simply positioned his forces in such a manner that the Ottoman superiority in numbers never became as big as an advantage it could have. Isfendiyar Bey was using the local terrain against the Ottomans as the hills and passages of the region confused the Ottoman navigators. Growing impatient and angry at the irregular tactics of his opponent, Yakub I was outmatched. But by this point, the most trusted and experienced Ottoman commander, the old and wizened Evrenos Bey returned to Anatolia after having defeated the local Albanian tribes in Berat. Evrenos Bey managed to convince Yakub I to hand over military command to him as Yakub I acknowledged that the military capabilities of Evrenos Bey were far greater than his own.

In a wily move, Evrenos Bey decided to stop targeting Kastamonu and instead marched towards Sinope, forcing Isfendiyar Bey to follow after him to protect the city from attack, however his strategy of simply outmaneuvering the Ottomans by positioning himself on their rear backfired against him as he was too late to stop Sinope from being captured. A 10,000-strong detachment led by Yigit Bey managed to capture Sampsouta [2] shortly afterward. Now cut off from the coast, from where he was receiving most of his economic aid from the Genoese, Isfendiyar Bey was forced to give battle near Talipler east of Kastamonu in July 1391, which ended in Candar defeat. Evrenos Bey entered Kastamonu on July 12 1391 with Isfendiyar Bey and Alaeddin Bey being captured during the previous battle.


Gazi Evrenos Bey

The Anatolian War (1389 – 1391) as it became known ended in the Ottoman annexation of the Germiyan, Karamanid and Candar Beyliks. For his part in outmaneuvering Isfendiyar Bey, Evrenos Bey was made Chancellor of the Ottoman Imperial Council, the second highest governmental title in the Ottoman Empire after Grand Vizier. Alaeddin Bey was subsequently executed and Isfendiyar Bey and Suleyman Bey spent the rest of their lives imprisoned alongside Yakup II of Germiyan. In order to appease his little sister, Yakub I made the former Karamanid territories into the Eyalet of Konya, which he promised to his nephew, Mehmed, the eldest son of Nefise Hatun in the future.

In what became normality for the superfluous Sultan, Yakub I returned to Adrianople with a great amount of pomp, which was in direct contrast with his rather humble father and grandfather, both of whom had disliked the flaunting of their dynastical and national wealth. Though many chroniclers and contemporary historians have leveled heavy criticism towards Sultan Yakub I regarding his continued luxurious attitude throughout the entirety of his reign, Yakub I had more than just grandiosity in mind when he committed such acts. He was making it clear to the ever-growling Europeans that he was a monarch of equal caliber to them, much like the grand processions of the monarchs of Hungary, Poland, France, and England. He was also making it clear to the remaining Beyliks in Anatolia who was the strongest power in the region. Though it is clear that Yakub I enjoyed showing off throughout his reign, we mustn’t ignore the psychological aspects of his luxurious attitude either.

But as Yakub I settled down in Adrianople doting on his daughter and reconciling to a degree with his Bulgarian wife, Yakub I had to deal with the death of Emperor John V who died on September 11, 1391. His son Manuel was still in Bursa under honorary house arrest. In his right as Suzerain, Yakub I needed to exert power over the succession, lest the hungry falcons in Constantinople play against him. Upon receiving news of the death of the old Emperor, Yakub I sent for Manuel who was transported from Bursa to Adrianople in record time and was proclaimed Byzantine Emperor by Yakub I. With an Ottoman contingent and with the traditional Byzantine guards who had followed Manuel into honorary house arrest, Manuel entered Byzantine territory on October 2 and was proclaimed Emperor Manuel II four days later in Constantinople in the Hagia Sophia.


Manuel II

While the two sovereigns had enjoyed personal peace with one another previously during the negotiations at Antalya a year prior, the two sovereigns were now on a collision course as Manuel II began to eye western Christendom as a potential player in freeing the Byzantines out of Ottoman rule once and for all. And further problems awaited Yakub I as the recent conquests would not be digested so easily.

- In The Hands of God: Rise of the Ottomans - Zubair Al-Sulaiman, Hejaz Press, @2020 AD

[1] – Philadelphia before its annexation in 1390/91 made around ~1600 ducats for the Ottomans in trade revenue annually.
[2] – Samsun.

1390: Yakub I defeats the Germiyan Beylik and annexes it. John V is deposed by John VII, but Yakub I supports John V to regain the Byzantine throne. In return the Byzantines give higher tribute, expel the troublesome Genoese and give a large contingent troops to support Yakub I. Yakub I has a daughter – Azadeh Hatun.
1391: Yakub I defeats the Karamanids and Evrenos Bey defeats the Candarli Beyli, annexing the regions into the Ottoman Empire. Manuel II begins to look for outside help to defeat the Ottomans.
So will there be a Nicopolis ITTL? I suspect butterfly affect might alter time and place but nevertheless a European coalition against Ottomans is given.
So will there be a Nicopolis ITTL? I suspect butterfly affect might alter time and place but nevertheless a European coalition against Ottomans is given.
Yes, a general anti-Ottoman coalition is in the making, though the circumstances will be different from the OTL Crusade of Nicopolis.