The Russian-Israeli intersections in the Middle East sway sometime from being distinctly pragmatic to peculiar arenas when it comes to the ongoing Syrian conflict. Through adopting the lens of Neoclassical Realism as a theory of international relations, this paper demonstrates how the Syrian conflict - due to its importance to both Israel and Russia - leads both countries to participate in positional competition in the region, engage in limited but effective cooperation, and try to stem the erosion of state-centric governance. The unique ties between the two countries in terms of their religious and ethnic composition further underpin these activities, and how they translate into a particular decision-making process down to the domestic level. The controversial, yet pragmatic approaches of the two countries, often associated with the “iron fist” policies of both Netanyahu’s and Putin’s statecraft, are reflective of a distinct mixture of domestic homogeneity and vertical leadership-centered power aggregation, blended with military boldness in the constant quest for security.