The aim of this paper is to trace the evolution of 'Alawi society and particularly of the 'Alawi ayan (local notable) class in the province of Tripoli in a comparative framework. Generally ignored in both Ottoman imperial and Arab provincial history, the notable landowning or land-controlling families of north-western Syria shared many socio-political features with, and faced similar economic challenges as, the classes categorized as nobility, Landadel, gentry, etc. in northern and Mediterranean Europe in the early modern period. Beginning with the so-called "crisis of the aristocracy" of 1560-1640, which was marked by the military decline of the feudal cavalry, inflationary pressures and the systematic indebtedness of provincial office holders vis-à-vis an increasingly centralized fiscal bureaucracy, the history of the provincial landed elite throughout Europe and the eastern Mediterranean has been one of struggle, redefinition and adjustment to the new realities of the modern state. The first part of this paper will exploit Ottoman tax censuses (Tahrir Defterleri) to show how the Ottoman state attempted to assert fiscal sovereignty in the region after the initial conquest, both through the imposition of discriminatory taxes on the ‘Alawi population but also by co-opting local tribal leaders as government intermediaries. The second part will draw on both the tax farming records of the provincial administration of Tripoli and Ottoman executive orders (Mühimme Defterleri), so as to showcase the venality of government office, the recruitment of brigand bands by the notable families and the rise of a new class of ennobled gentry in north-western Syria not as a phenomenon unique to the 'Alawite community, but rather as expressions of fundamental structural changes in the shared political economy of early modern European and the Middle East.