Yusuf Sayfa Pasha (Arabic: يوسف سيفا باشا, romanized: Yūsuf Sayfā Pāsha; c. 1510 – 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.
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