This chapter follows the rise to power of the Shamsins, the Bayt al-Shillif, and associated ʻAlawi families as Ottoman tax concessionaries. It shows that their position of local autonomy, rather than having evolved out of some domestic or “tribal” leadership structure, resulted from a paradigm shift in Ottoman provincial administration as well as from a very favorable economic context, in particular the development of commercial tobacco farming in the northern highlands around Latakia. If the eighteenth century witnessed the emergence of a veritable Ottoman–ʻAlawi landed gentry, it also saw increasing social disparities lead to large-scale emigration away from the highlands toward the coastal and inland plains as well as toward the Hatay district of what is today southern Turkey.