Until the end of thirteenth century, Osman I's conquests include the areas of
Bilecik (Belokomis),
Yenişehir (Melangeia),
İnegöl (Angelokomis) and (Köprühisar), and Byzantine castles in these areas. According to Shaw, Osman's first real conquests followed the collapse of
Seljuk authority when he was able to
occupy the fortresses of Kulucahisar and Eskişehir. Then he captured the first significant city in his territories,
Yenişehir, which became the Ottoman capital. Alarmed by Osman's growing influence, the Byzantines gradually fled the Anatolian countryside. Byzantine leadership attempted to contain Ottoman expansion, but their efforts were poorly organized and ineffectual. Meanwhile, Osman spent the remainder of his reign expanding his control in two directions, north along the course of the
Sakarya River and southwest towards the
Sea of Marmara, achieving his objectives by 1308. Although Osman did not physically participate in the battle,
the victory at Bursa proved to be extremely vital for the Ottomans as the city served as a staging ground against the Byzantines in
Constantinople, and as a newly adorned capital for Osman's son,
Orhan. Ottoman tradition holds that Osman died just after the capture of Bursa, but some scholars have argued that his death should be placed in 1324, the year of Orhan's accession.
Conquest of Karacahisar After establishing his beylik, Osman had to fight on two fronts: one against the Byzantine, and the other against the Turkomen beyliks that opposed his rule, especially the Germiyanids. Osman focused on expanding at the expense of the Byzantines, and since that time, the primary Ottoman goal became the conquest of the remaining Byzantine lands. Some accounts indicate that the first battle Osman launched against the Byzantines was aimed to revenge a defeat that he suffered in the spring of 1284 or 1285, where the Byzantines, led by the
Tekfur of Bursa, ambushed him and his men. It is in doubt that Osman knew about this ambush from one of his spies. Nevertheless, he chose to clash with the Byzantines and he was defeated and forced to withdraw with casualties, including his nephew Koca Saruhan bey, son of
Savcı Bey. Based on this, around 1286, Osman went forward to Kulacahisar at the head of a military force of three hundred fighters, it was a fortress located two leagues away from İnegöl, within the scope of mount
Uludağ. The Emir attacked the fort at night and managed to
conquer it, extending his beylik northwards toward Lake İznik's proximity. The Ottoman victory at Kulacahisar triggered the fort's governor, who refused to be a subordinate subject to a Muslim ruler, especially a border Emir, so he allied himself with
Karacahisar's governor, and both men agreed to fight the Muslims aiming at retaking all Byzantine lands that were lost recently. Thus, the Ottomans and the Byzantines met again in battle, somewhere between Bilecik and İnegöl, where fierce fighting took place in which Osman's brother Savcı Bey and the Byzantine commander Pilatos were killed. The Battle ended with an Ottoman victory. Then, the Ottomans entered Karacahisar where they, reportedly for the first time, converted the town's church into a mosque. Osman appointed a
Qadi (magistrate) and a
Subaşı (chief of police) for the newly conquered city. Historians differed in determining the date of this conquest, yet none made it prior to 1286, or exceeding 1291. Osman made his new city a staging base of his military campaigns against the Byzantines, and ordered that his name be delivered at the Friday
khuṭbah, which was the first manifestation of his sovereignty and authority. The Sultan also bestowed upon Osman the governance of all the land he did conquered as well as the towns of
Eskişehir and
İnönü. Moreover, The Seljuk Sultan issued a decree exempting Osman from all types of taxes. Osman also received several gifts from the Sultan reflecting the new high stature to the Seljuk court. These gifts included: a golden war banner, a
mehter (war drum), a
tuğ (a pole with circularly arranged horse tail hairs), a tassel, a gilded sword, a loose saddle, and one hundred thousand
dirhams. The decree also included the recognition of Osman's right to be mentioned in the Friday
khuṭbah in all areas subject to him, and was permitted to mint coins in his name. Thus, Osman became a Sultan, but lacking only the title. It is narrated that when drums were beaten announcing Sultan's Kayqubad's arrival, Osman stood up in glorification, and remained so till the music halted. Since that day, Ottoman soldiers enacted standing in glorification for their Sultan whenever drums were beaten.
Conquest of Bilecik, Yarhisar, and İnegöl Soon after the conquest of Karacahisar, Osman marched with his soldiers north towards
Sakarya River. Upon his arrival there, he raided and looted the forts of
Göynük and
Yenice Taraklı. Many argue that during this time, Osman received a message from his Byzantine friend Köse Mihal, warning him of a secret conspiracy that was being prepared by the
tekfurs of Bilecik and Yarhisar. The two were aiming at killing Osman after inviting him to attend their children's wedding. Osman was disappointed by being betrayed by Bilecik's tekfur. That is because he considered the relationship with Bilecik to have been built on trust and good faith, as demonstrated by the aforementioned custom of his clan leaving their belongings in this fortress whenever they moved between grazing areas. Osman devised a plan to escape the trap and take over the fortress. He sent forty of his soldiers carrying some of the clan's belongings to be kept in Bilecik, while most of its inhabitants were outside attending the wedding. Once his men entered the fort, they quickly overpowered its small garrison, and it fell to the Ottomans. Then, Osman went to the feast followed by some Byzantine knights who were easily ambushed by his men later. A short battle took place in which Osman was victorious, and most of the Byzantines were killed. After that, Osman rode towards Yarhisar and took it by surprise; A large part of the fort's garrison was killed, while the rest were taken prisoners. The ''tekfur's'' daughter Holophira, was also captured in this action, she soon became Osman's daughter in law, having married his son Orhan sometime later, and her name was changed in Bayalun Afterwards, Osman and several of his men took over all towns and villages surrounding İnegöl, before laying siege on the fort itself and taking it with ease. Osman ordered the execution of İnegöl's
tekfur since he was known for persecuting his Muslim neighbours, then placed a new garrison for the town, and distributed the loot among his men. At the same time, the Seljuk Sultanate of Rûm was seeing its final days. The Sultanate grip was slowly weakened over its Turkoman Beyliks. Sultan Alâeddin Kayqubad III became deeply unpopular after he purged the Seljuk administration of his predecessor's men with extreme violence. This prompted the Mongol Ilkhan
Mahmud Ghazan to call upon Kayqubad to appear before him, and once the latter did in 1302, he was executed and replaced with his predecessor
Ghiyāth ad-Dīn Mas'ūd bin Kaykāwūs to keep the peace in Anatolia. According to another account, Mongol and
Tatar hordes raided Asia Minor in 1300, and killed Sultan Kayqubad in his capital Konya. It was also said that Kaykāwūs himself killed his rival, coveting his own return on the throne. Another story suggests that Kayqubad escaped and sought refuge in the Byzantine court where he remained until his death.
Battle of Bapheus Soon after Osman secured his independence and established control over all fortresses he conquered, he sent messages to all remaining Byzantine
tekfurs in Anatolia asking them to choose between accepting Islam, Ottoman sovereignty and paying
jizyah, or war. Some of these
tekfurs ended up accepting Islam, including Osman's old friend Köse Mihal, who became the Turkic leader's companion, and would play a considerable part in the upcoming expansions of the Osmanic beylik. His descendants became known in Ottoman history as
Mihaloğulları (children of Michael, plural of
Mihaloğlu). Other governors acknowledged Osman's sovereignty, while the rest kept their loyalty to the Byzantine Emperor. Thus, Osman started harassing their fortresses such as Bursa and
Nicaea which was besieged in 1301. The Ottoman raids also threatened the port city of
Nicomedia with famine, as the Ottomans roamed the countryside prohibiting peasants from harvesting wheat. This provoked Bursa's
tekfur among others to unite their efforts to eliminate this new emerging Islamic power. In the spring of 1302, Emperor
Michael IX launched a campaign that reached south to
Magnesia. The Ottomans, awed by his large army, avoided an open battle. The Emperor sought to confront The Ottomans, but he was dissuaded by his generals. Encouraged by that, The Ottomans resumed their raids, virtually isolating the Emperor at Magnesia. Soon, the imperial army started dissolving without engaging in a single battle, that is because the local troops left to defend their homes which were continuously raided by the Ottomans, and the
Alan mercenaries left as well, aiming to rejoin with their families in
Thrace. The Byzantine emperor was forced to withdraw by the sea, followed by a wave of refugees. To counter the threat to Nicomedia, Michael's father,
Andronikos II, sent a Byzantine force of some 2,000 men (half of whom were recently hired Alan mercenaries), under the
megas hetaireiarches, Giorgios Mouzalon, to cross the
Bosporus and relieve the city. The Byzantine and Ottoman armies
eventually met on 27 July 1302 at the plain of Bapheus located between Nicomedia and Nicaea. The Ottoman army consisted of light cavalry under Osman himself, and they numbered around 5,000, while the Byzantines numbered around 2,000 men. The Muslim cavalry charged toward the Byzantines fast, whose Alan contingent did not participate in the battle. As a result of the attack, the Byzantine line was broken, forcing Giorgios Mouzalon to withdraw into Nicomedia under the cover of the Alan force. Bapheus was the first major victory for the nascent Osmanic Beylik, and of major significance for its future expansion: the Byzantines effectively lost control of the countryside of
Bithynia, withdrawing to their forts, which became isolated and fell one by one eventually. The Byzantine defeat also sparked a mass exodus of the Christian population from the area into the European parts of the empire, further altering the region's demographic balance.
Conquest of Yenişehir and Its Surroundings After securing his northern borders by reaching the Black and Marmara seas, Osman turned his attention towards the southern borders of his beylik. Thus, he attacked the Byzantine towns, villages, and fortresses surrounding the city of
Yenişehir preparing to conquer it. Osman sent a large campaign to the fortress of Yāvandhisar and annexed it. Then, he attacked Yenişehir, took it with ease, and made it his temporary capital after fortifying and strengthening its defenses. Soon after that Osman started sending more campaigns against the remaining Byzantine cities conquering several fortresses including
Lefke,
Akhisar,
Koçhisar, Yenicehisar,
Marmaracık, and
Köprühisar. In fact, conquering the aforementioned forts aimed at imposing a security belt around Yenişehir, thus Osman surrounded it with a series of front forts to ward off any invasions.
Conquest of Bursa With Yenişehir in his hands, Osman focused his efforts on isolated large cities starting with Bursa, unaware that this would be his last campaign. He gave the orders to start building two forts overseeing and surrounding the city, then, when the construction was completed, Osman provided the forts with large garrisons. This allowed his men to tighten the blockade and prevent any provisions reaching Bursa. The Ottoman siege lasted between six and nine years, this was due to the fact that the Ottomans had no
Siege engines and they had never captured a large fortified city before. During the long siege, Osman and some of his military commanders conquered the smaller Byzantine fortresses on the vicinity of the beylik, in which Several
tekfurs acknowledged Osman's sovereignty, and became among his subjects, some of them accepting Islam in the process. Soon after that, Osman started suffering from
Gout, and couldn't accompany his men in any more campaigns or witness the
Siege of Bursa, so he entrusted his son Orhan to complete this major task, while he retired in his capital. Orhan's continued the siege without any fighting, but he continued isolating Bursa from its surrounding forts, conquering
Mudanya to cut off the city's connection to the sea. He also captured the city of
Praenetos on the southern coast of
İzmit, changing its name to Karamürsel, after the Muslim leader who took it "Karamürsel Bey". The last fort to fall was Beyce, which was considered Bursa's key as it overlooked it, and it was renamed
Orhaneli. Saroz, the garrison's leader, surrendered to Orhan and pledged allegiance to his father Osman. He also converted to Islam and was given the title of "Bey" out of respect to his courage and patience during the long siege. According to some sources, Osman died just before the fall of the city, ==Family==