Yusuf Sayfa Pasha (; – 22 July 1625) was a chieftain and multazim (tax farmer) in the Tripoli region who frequently served as the Ottoman beylerbey (provincial governor) of Tripoli Eyalet between 1579 and his death.

Yusuf or his family may have been Kurdish or Turkmen levends (tribal irregulars) from Marash and were established in Tripoli's vicinity by at least the 1510s–1520s. He became a multazim in Akkar subordinate to the Assaf chieftains of the Keserwan for most of his career until his promotion to the rank of pasha and appointment as Tripoli's first beylerbey in 1579. Hostilities consequently ensued with the Assafs, ending with Yusuf's assassination of their last chieftain in 1591 and his confiscation of their tax farms. His takeover of the Keserwan and Beirut prompted his first confrontation with Fakhr al-Din II, the Druze chieftain and sanjak-bey (district governor) of Sidon-Beirut in 1598. He was given command by the Sublime Porte (Ottoman imperial government) over the armies in the region of Syria to suppress the rebel Ali Janbulad of Aleppo in 1606. After a series of defeats at Hama, Tripoli and Damascus, he submitted to Janbulad at Krak des Chevaliers (Hisn al-Akrad), though the rebellion was suppressed in 1607.

Relations with the Ottomans deteriorated over the next ten years, a period in which Fakhr al-Din gained steady advantage over Yusuf, who was abandoned by most of his local allies and his nephews. To prevent Fakhr al-Din from gaining total control over Tripoli, the Porte reappointed Yusuf beylerbey in 1619. He remained under financial strain with large debts due to the Porte and owed to Fakhr al-Din, who gained control over most of the eyalet's districts. With his death in 1625, the Sayfas' power gradually dissipated and most of the family was exterminated by the Ottomans by the mid-17th century.

Yusuf was noted by contemporary historians for his generosity and patronage of poets and Sufis, which contributed to his poor financial state. Neither he nor his family developed Tripoli or its eyalet, which declined economically in contrast to the thriving domains of Fakhr al-Din. Although he was viewed favorably by the Sunni Muslims of Tripoli and Akkar for his loyalty to the Ottomans, he was resented by the Maronite peasantry for executing unpopular and ruinous government measures.

Origins Conventionally, the Sayfa family were considered to be Kurds based on the 19th-century, local chronicle of Tannus al-Shidyaq. The 16th-century Damascene historian and intimate of Yusuf, al-Hasan al-Burini, noted that the Sayfas were relatives of the Dulkadirids, a Marash-based Turkmen tribal dynasty. The 17th-century Maronite patriarch and historian Istifan al-Duwayhi referred to them as Turkmens. The modern historians Kamal Salibi and Abdul-Rahim Abu-Husayn concur that they were Turkmens in origin. The modern historian Stefan Winter holds that the Sayfas were probably of Kurdish origin but affiliated with the Dulkadirid Turkmens. Abu-Husayn notes that the Sayfas had been levends, citing the generally authoritative Ottoman historian Mustafa Naima (d. 1716). According to Naima, Yusuf hailed from Marash in the Anatolian–Syrian borderlands and moved from there to Tripoli.

Abu-Husayn surmises that the Sayfas may have arrived in Tripoli Sanjak during the dispersal of the Dulkadirids and their affiliates shortly before 1526 or shortly after their reestablishment that year. The sanjak was a subdivision of Damascus Eyalet spanning the coastlands of Ottoman Syria from Latakia southward to Byblos and northern Mount Lebanon and the Alawite Mountains. The establishment of Turkmen and Kurdish military colonies around Tripoli started during Mamluk rule (mid-13th century–1516) to secure the strategic port city's mountainous hinterland and protect the roads connecting the Syrian coast with the major cities of the Syrian interior plains. The rugged ranges separating Tripoli from the Syrian interior, namely northern Mount Lebanon and the Alawite Mountains, were dominated by Catholic Maronites and the heterodox Muslim Alawites, two communities viewed with suspicion by the Sunni Muslim Mamluks and Ottomans, who conquered Mamluk Syria in 1516.

Duwayhi places Yusuf in Tripoli or its vicinity in 1528. He was likely ten to twelve years old at the time. Although Abu-Husayn asserts that Yusuf was the first member of the Sayfa clan whose name is recorded in the sources, Ottoman tax records name a certain Muhammad Sayfa as the holder of timars (fiefs) in the nahiyas (subdistricts) of Arqa, Batroun, Dinniyeh, Futuh Bani Rahhal, Akkar, Hisn al-Akrad, Manasif and Tartus, all in the Tripoli Sanjak, in 1519. Al-Shidyaq's chronicle records the name of Yusuf's father to be Muhammad. The tax records also indicate that a son of Muhammad Sayfa, Ibrahim, held timars in Arqa in 1534–1537 and 1548–1549; after Ibrahim's failure to report to the Baghdad front in the war with Safavid Iran in 1553, his timars were transferred to a certain Yusuf.

Establishment in Akkar Yusuf was headquartered in the fortress village of Hisn Akkar (Gibelacar). He formed ties with the local multazims (holders of iltizam, i.e. tax farms) upon moving to the area. Tax farming was the predominant mode of tax collection in Syria where sanjaks and nahiyas were farmed out to local strongmen for limited terms in return for a fixed amount of money. From Hisn Akkar Yusuf controlled Jabal Akkar, the northernmost part of Mount Lebanon, and possibly the Homs Gap plain at Jabal Akkar's northeastern edge. He and his paternal kinsman Hasan were given joint control of a farm in Akkar by the authorities in 1571.

The tax farms in Jabal Akkar were likely subleased to Yusuf from Mansur ibn Hasan, the head of the Turkmen Assaf dynasty. The Assaf multazims were headquartered from the 13th century in the village of Ghazir in the Keserwan area in central Mount Lebanon. Mansur leased the Jabal Akkar tax farm and other tax farms in the Tripoli Sanjak from Muhammad Agha Shu'ayb, the chieftain of a long-established military family based in the fortress of Arqa in the Akkar Plain, which had held the tax farms for all or part of the Tripoli region from 1523. Mansur may have encouraged Yusuf's establishment in Jabal Akkar to undermine the Shu'aybs by installing an ally in their vicinity. Conflict broke out soon afterward between the Sayfas and Shu'aybs in 1528 when the former withheld tax revenues from the latter. The Sayfa family, lacking the local power base of the Shu'aybs, consequently fled Akkar. They temporarily found refuge in Baruk under the protection of Qurqumaz ibn Yunis of the Ma'n dynasty, a long-established family of Druze chieftains and tax farmers who controlled the Chouf area in southern Mount Lebanon.

Not long after their displacement, the Sayfas were assisted by Mansur, who had also owed Muhammad Agha taxes. The Sayfas, Assafs and Ma'ns assaulted Arqa in 1528 and routed the Shu'aybs, while Mansur had Muhammad Agha assassinated. The Shu'aybs lost their local importance thereafter, and Mansur reestablished the Sayfas in their Akkar stronghold. After the demise of the Shu'aybs and Mansur's subsequent elimination of other local rivals he became the preeminent strongman of the Tripoli region; the Sayfas, with whom he continued to be allied, became his fiscal subordinates and there were no reported conflicts between Mansur and Yusuf before 1579. By then, Mansur had become the most powerful chieftain in Syria, acquiring the tax farms of the neighboring sanjaks of Homs and Hama and the port town of Beirut.

Governorship of Tripoli First term

The Sublime Porte (Ottoman imperial government in Constantinople) designated the Tripoli Sanjak as its own eyalet in 1579, likely to check Mansur's growing power and to strengthen Ottoman authority over Mount Lebanon and its environs in general; Duwayhi holds the Porte was responding to complaints about Mansur's killing of local rivals, which Abu-Husayn determines was used by the Ottomans as a pretext to keep a closer watch on Mansur because of his stockpiling of firearms acquired from the Ottoman conquest of Cyprus in 1571 and suspected ties through his Maronite advisers with Catholic European powers increasingly active in the eastern Mediterranean. Yusuf was promoted to the rank of pasha and appointed the new eyalet's first beylerbey. The subsequent loss of tax farms in Tripoli Eyalet, such as the predominantly Maronite area of Bsharri, and the appointment of Yusuf, weakened the Assafs.

According to Abu-Husayn, Yusuf was selected after "careful deliberation" by the Ottomans. On the one hand, the Porte determined Yusuf was well-positioned to efficiently manage the eyalet by dint of his long career in the Tripoli area, his ties to the local chiefs and his understanding of local politics. On the other hand, he would be easier to control because he lacked the tribal and peasant power bases of the Assafs and Ma'ns; further, Yusuf's headquarters in Hisn Akkar was more accessible and thus easier to reduce than the headquarters of other local chiefs nestled deep in the Lebanon range. By appointing Yusuf to a rank and position above that of the Assafs, his hitherto superiors, the Porte also aimed to undermine their alliance. The Sayfas' position was significantly strengthened with Mansur's death in 1580.

In 1585 an Ottoman punitive expedition was launched to suppress the local chieftains of Syria, who had long resisted government taxation and disarmament orders. While the expedition's commander Ibrahim Pasha attacked the Druze chiefs in the Chouf, the principal target of the expedition, a veteran commander, Ja'far Pasha al-Tuwashi, raided Hisn Akkar, an event which only Duwayhi mentions. During or shortly after the expedition, Yusuf was dismissed and replaced by Ja'far Pasha; Yusuf may have resisted his dismissal and Ja'far Pasha's raid against Hisn Akkar may have been the commander's response to his resistance. Following the government raids, most of the chiefs taken captive by the Ottomans were released to their home bases, including Mansur's son and successor Muhammad. The prominence of the Assafs was reconstituted by Muhammad, who became Yusuf's principal local rival. Muhammad had persuaded the Porte of his loyalty and was given the territory of Tripoli Eyalet, except for Tripoli city, as iltizam shortly after his release in 1585, once again placing Yusuf and his kinsmen in Akkar as fiscal subordinates of the Assafs; the Sayfas maintained their iltizam in Akkar, but were responsible to Muhammad, through whom they forwarded revenues to the Porte.

Second term Yusuf and Muhammad likely waged a struggle for political dominance of the Tripoli region afterward. By 1590 Yusuf had been reinstated as beylerbey in place of Ja'far Pasha, though he may have been reappointed before 1590. In that year he was ordered by the Porte to arrest the advisers of the Assafs from the Maronite Hubaysh family, the brothers Abu Sa'd Mansur and Muhanna, and to deal with certain tax and administrative matters. Yusuf's attempts to arrest the Hubaysh brothers likely instigated conflict between him and Muhammad. Duwayhi held that Yusuf owed Muhammad tax arrears, while Ottoman records indicate that Muhammad had owed taxes to the Porte, which ordered the beylerbey of Damascus to collect them with Yusuf's assistance shortly before Muhammad's death in 1590 or 1591. Muhammad had set out from Ghazir against Yusuf but was assassinated en route at Musayliha on Yusuf's orders. His death without progeny marked the end of Assaf power.