Skanderbeg and other students receiving military education in the Skanderbeg was sent as a hostage to the Ottoman court in Adrianople () in 1415, and again in 1423. It is assumed that he remained at 's court as for a maximum of three years, where he received military training at. The earliest existing record of George's name [ ] is the First Act of Hilandar from 1426, when John Castriot and his four sons donated the right to the proceeds from taxes collected from two villages in (in modern, ) to the Serbian. Afterwards, between 1426 and 1431, John Castriot and his sons, with the exception of Stanisha, purchased four (rights to reside on monastic territory and receive subsidies from monastic resources) to the Saint George tower and to some property within the monastery as stated in the Second Act of Hilandar. After, the sultan granted Skanderbeg control over one (land grant) which was near the territories controlled by his father.

His father was concerned that the sultan might order Skanderbeg to occupy his territory and informed Venice about this in April 1428. In the same year John had to seek forgiveness from the because Skanderbeg participated in Ottoman military campaigns against Christians. In 1430, John was defeated in battle by the Ottoman governor of, and as a result, his territorial possessions were extremely reduced.

Later that year, Skanderbeg continued fighting for Murad II in his expeditions, and gained the title of. Several scholars [ ] have assumed that Skanderbeg was given a fiefdom in in northern, because a certain 'Iskander bey' is mentioned in a 1430 document holding fiefs there. Although Skanderbeg was summoned home by his relatives when and Andrew Thopia along with other chiefs from the region between and organized a (1432–36), he did nothing, remaining loyal to the sultan. Skanderbeg's return to, 1444 (woodcut by ) In Albania, the rebellion against the Ottomans had already been smouldering for years before Skanderbeg deserted the Ottoman army. In August 1443, again revolted against the Ottomans in the region of central Albania.

Under Venetian patronage, on 2 March 1444, Skanderbeg summoned Albanian noblemen in the Venetian-controlled town of and they established a military alliance known in historiography as the. Among those who joined the military alliance were the powerful Albanian noble families of,,,,,, and, and also the Serbian nobleman of Zeta. Skanderbeg organized a mobile defense army that forced the Ottomans to disperse their troops, leaving them vulnerable to the of the Albanians. Skanderbeg fought a against the opposing armies by using the mountainous terrain to his advantage. During the first 8–10 years, Skanderbeg commanded an army of generally 10,000–15,000 soldiers, but only had absolute control over the men from his own dominions, and had to convince the other princes to follow his policies and tactics. Skanderbeg occasionally had to pay tribute to the Ottomans, but only in exceptional circumstances, such as during the war with the Venetians or his travel to Italy and perhaps when he was under pressure of Ottoman forces that were too strong. A woodcut of the in 1444 In the summer of 1444, in the Plain of Torvioll, the united Albanian armies under Skanderbeg who were under direct command of the Ottoman general Ali Pasha, with an army of 25,000 men.

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[ ] Skanderbeg had under his command 7,000 infantry and 8,000 cavalry. 3,000 cavalry were hidden behind enemy lines in a nearby forest under the command of. At a given signal, they descended, encircled the Ottomans, and gave Skanderbeg a much needed victory. About 8,000 Ottomans were killed and 2,000 were captured.

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Skanderbeg's first victory echoed across Europe because this was one of the few times that an Ottoman army was defeated in a pitched battle on European soil. On 10 October 1445 an Ottoman force of 9,000–15,000 men under Firuz Pasha was sent to prevent Skanderbeg from moving into Macedonia. Firuz had heard that the Albanian army had disbanded for the time being, so he planned to move quickly around the Black Drin valley and through Prizren. These movements were picked up by Skanderbeg's scouts, who moved to meet Firuz. The Ottomans were lured into the Mokra valley, and Skanderbeg with a force of 3,500 attacked and defeated the Ottomans.