He participated in the Albanian Declaration of Independence in Vlorë (November 1912) and was then assigned as a diplomatic agent to the British (1913), and bodyguard of Prince Wilhelm of Albania (1914).

[2][3] His family were Albanian Muslims which had migrated to Boletin from the village of Isniq near Deçan, due to a blood feud (gjakmarrja) though they ultimately hailed from Shala, in northern Albania.

[11] Following the emergence of the Albanian nationalist League of Prizren in 1878, Isa Boletini actively participated in the evolving political and military landscape of the region.

[13] During the Young Turk Revolution (1908), a large gathering in Firzovik of local urban notables and Muslim clergy (ulama) backed restoration of the constitution while Boletini on the side of the chieftains viewed that position as disloyalty to the sultan.

[citation needed] The Committee of Union and Progress, within c. a month of the restoration of the constitution, decided to address blood feuding matters in Kosovo, sentencing Albanians engaged in killings.

[20] Toward the end of 1908 aggressive measures was pushed by locals – Nexhip Draga and other notables in Kosovo viewed Boletini as a nuisance, threat and loyalist of sultan Abdulhamid II and lobbied the new Young Turk (CUP) government for his arrest and destruction of his kulla (tower house).

[20] Class differences of Draga, a landowner wanting law and order and Boletini, a chieftain preferring maintenance of old privileges and autonomy along with the disagreement in Firzovik about the restoration of the constitution resulted in the rift.

[20] The Ottoman government needing a pretext for action sent an officer with some soldiers to serve a court order to Boletini for illegally receiving land from the sultan that previously belonged to a local named Haxhi Ali.

[21] Ottoman forces arrived at his stronghold shortly after, resulting in an attack and fierce firefight with Boletini escaping with a small group of men and his kulla was razed to the ground.

[21] After the events with Boletini, the Ottoman army then went throughout Kosovo and razed other kullas of several chieftains involved in the deruhdecilik (protection "racket") system.

[22] On 15 May 1909, the Young Turks, continuing their former policy of denying the Albanians national rights, sent a military expedition to the Kosovo Vilayet to stop the growth of hostile attitudes to the government and break resistance of the peasants, who refused to pay taxes which Istanbul had introduced.

[23] Cavid Pasha, the new commander of the division at Mitroviça, was ordered to carry out a succession of military operations against the Albanian mountaineers, in particular the capture of Boletini.

[24] The Young Turks expressed the view through their newspaper Tanin that most Albanians of the area had given their besa (pledge) not to go against the government apart from Boletini and a few supporters.

[24] On account of the attempts of the authorities to collect taxes which hitherto had been paid almost entirely by the Christians, serious disturbances broke out among the warlike Muslim tribes of northern Albania.

[28][29] At first, Montenegro ignored his presence, but on 15 June, after numerous protests from the Ottoman ambassador, escorted Boletini and his thirteen followers away from the Albanian border.

[31] By 20 May, Boletini alongside other Albanian leaders were present at a meeting in Junik where a besa (pledge) was given to wage war on the Young Turk government through armed insurrection in Kosovo Vilayet.

[34] During the 1912 uprising, while waiting for an Ottoman response to the demands of the rebels, Boletini and other leaders of the rebellion ordered their forces to advance toward Üsküb (modern Skopje) which was captured during August 12–15.

[31] On August 18, the moderate faction led by Prishtina managed to convince Boletini, and other leaders Idriz Seferi, Bajram Curri and Riza Bey Gjakova of the conservative group to accept the agreement with the Ottomans for Albanian sociopolitical and cultural rights.

[40] In August, Colonel Dragutin Dimitrijević "Apis", the head of the Serbian Black Hand organization, sent a letter requesting Boletini and his men to assist the Serbs in fighting the Ottomans.

[3] The Albanian delegation wanted a Kosovo within the borders of the newly founded state of Albania, however the Great Powers said no and ceded the region to Serbia.

A tenacious Albanian band of fighters under the command of Boletini, now Minister for War in the Provisional Government, made a successful attack on the frontier town of Debar and captured it from the small Serbian garrison, which had to retire after suffering severe losses.

It was later raised on top of a hill in Visekovc and on 12 August 1912, Boletini with thirty of his men, carried it through the streets of Skopje, which at the time was part of the Vilayet of Kosovo.