His rebellion, launched to avenge the execution of his uncle Huseyn ibn Janbulad by the commander Jigalazade Sinan Pasha in 1605, gained currency among northern Syria's Kurdish, Turkmen and Arab tribes and expanded to include local Syrian governors and chiefs, most prominently Fakhr al-Din Ma'n of Mount Lebanon and his erstwhile enemy Yusuf Sayfa Pasha of Tripoli.
Ali formed a secret military alliance with the Grand Duke of Tuscany, Ferdinand I, with the explicit aim of jointly destroying the Ottoman Empire and establishing the Janbulad family as the sovereigns of Syria.
Ali's burgeoning ties with several Celali revolt leaders, whose influence spanned central Anatolia, Cilicia and part of Mesopotamia, posed a major threat to the Empire at a time in which it was at war with Austria-Hungary in the west and Safavid Iran in the east.
The prospect of a foreign-backed, wide-scale rebellion in the Ottoman heartland prompted Grand Vizier Kuyucu Murad Pasha to launch an expedition against Ali.
[3] According to the historian William Griswold, the hereditary appointments to the militarily strategic and lucrative posts were "generous and represented considerable respect" by the Sublime Porte (imperial Ottoman government in Constantinople) for Janbulad.
[8] By 1600 he had accrued significant wealth and influence with the Porte, and a well-trained and well-compensated army of sekbans, as well as his Kurdish tribesmen and Turkmen and Arab tribal levies from northern Syria.
[13] In May 1606 he had lodged a formal request to the imperial government for the governorship of Aleppo and a vizier post in Constantinople and pledged 10,000 troops to the Ottoman campaign against the Safavids.
[15] As a result, Yusuf, a Kurdish chieftain with a local power base in his province and a career Ottoman official, sensed a dual opportunity: he could neutralize the Janbulads, whose hegemony he feared, and in the process gain significant prestige with the sultan for suppressing Ali without the costly intervention of an imperial army.
[17] Ali and Fakhr al-Din met in the northeastern Beqaa Valley, at the source of the Orontes River, and devised plans to capture or kill Yusuf.
[18] Their first target was Tripoli, the principal source of Yusuf's wealth and strength, against which Ali dispatched his paternal first cousin Dervish ibn Habib, who captured the city.
Although Dervish seized the valuables stockpiled in the inner citadel of Tripoli's castle, Ali strictly forbade the city's plunder in a bid to demonstrate to its inhabitants that his rule would be mild and generous.
[19] They cautiously kept Musa on side, sending him to lobby military factions in Damascus to abandon Yusuf, but forced him to step down from his chieftainship in favor of his kinsman Yunus al-Harfush.
[21] Although control of Damascus would seal his paramountcy in the Syrian region, Ali was mindful of the city's distance from his Aleppine power base and its importance to the Porte as the Empire's main marshaling point for the annual Hajj pilgrimage caravan to Mecca.
Closer to his territorial power base Ali had the absolute loyalty of his Janbulad clan, followed by the Kurdish tribal beys and the nomadic Arabs of Kilis and Azaz.
The revolts were precipitated by economic pressures in rural Anatolia stemming from overpopulation, a significant drop in the value of local silver and subsequent inflation, the inability of graduates from madrasas to find employment combined with the increasing availability of muskets among the peasantry.
Ferdinand sought to reconquer Cyprus for the Christians and had similar designs on the Holy Land, while also seeking commercial ties with Aleppo,[31] the principal outlet for the export of Iranian silk and other commodities to European markets.
[31] It explicitly stipulated joint efforts toward the weakening and eventual destruction of the Ottoman Empire, the strengthening of the Janbulad dynasty and recognition of Ali as "Prince and Protector of the Kingdom of Syria".
Janbulad was required by the treaty to assist a European conquest of Jerusalem and recognize the city's Christian denominational redirection to Roman Catholicism from the Eastern churches.
[2] Ottoman and Safavid sources do not mention ties formed between Ali and Shah Abbas, who adopted a policy of allowing Celali rebels safe haven in his territory.
[30] All of Ali's communications with non-Ottoman regional powers were kept secret, though the ties with Tuscany were likely uncovered by government spies and the failed Tuscan invasion of Chios in 1607 probably riled the new grand vizier, the Empire's most celebrated and feared veteran commander Kuyucu Murad Pasha.
His appointee to Marash, Haydar Bey, was unable to oust the grand vizier's general Zulfikar Pasha from the post and the latter's forces remained positioned north of the Taurus Mountains against Ali.
Military assistance from Tuscany in the relatively modest form of five cannons and 1,000 musket barrels was also not slated to arrive for another six to ten months,[42] while a Tuscan attempt to invade Cyprus, partly to support Ali, was repulsed in August.
[43] Ali publicly proclaimed in Aleppo that he served only Sultan Ahmed and threatened the grand vizier "would taste the strength of his army" should he proceed toward his domains.
Zulfikar's patrols engaged with Ali's troops for three days while the grand vizier's army rested until 23 October when clashes culminated into a pitched battle.
The two armies encountered at Oruç Ovasi (the Meadow of the Ritual Fasting), a narrow area opening into a plain bound by mountains to the west and the Afrin River to the east.
The following day Tiryaki Hasan Pasha put to use the imperial army's field artillery, hiding the batteries behind the slopes of Oruç Ovasi.
He had the imperial infantry and cavalry feign a slow retreat, thereby encouraging Ali's sekbans to pursue them on the field and expose them to the fire of the hidden artillery.
The forces in the citadel refused to surrender, compelling Murad Pasha to appeal to its inhabitants, especially Ali's wives, to spare themselves of his army's assaults and offer them clemency.
His invitation to Tavil was rejected, while his efforts to recruit Kalenderoglu Mehmed and Kara Said fell through as they were in negotiations with the grand vizier and refused to subordinate themselves to Ali's leadership.
Upon returning to Constantinople from his campaigns against the Celali rebels in Anatolia in the summer, Murad Pasha learned of Ali's circumstances and ordered his imprisonment in the Belgrade fortress.