Historically, Russia and Iran have shared a complex relationship that continues to color the contours of their present bilateral dealings. The complicated patterns of cooperation and conflict between them have been determined by a host of domestic and external factors on both sides, most pronouncedly manifested by their respective relationship with the USA. This article attempts to analyze Russia’s relationship with Iran in the geopolitical setting of 414144023133the post-Cold War period. The aim of the article is to see how this bilateral relationship has evolved over time, exploring the underlying changes and continuities, from the Yeltsin period to the Putin era, in which Russia’s foreign policy has come to be characterized by an assertive fervor. Russia, under President Putin, has been pushed further toward the globalist end as the USA has attempted to consolidate Western values and institutions, at times to the extent of ignoring and undermining the principles of international law. It is within this broader context that this article will analyze the extent to which Russia’s disillusionment with the USA has played a role in pushing Russia toward adopting a pragmatic and flexible approach from time to time vis-à-vis Iran, in general, and the Iranian nuclear crisis, in particular. The article argues that Russia’s active involvement in minimizing the impact of sanctions on Iran and its method of dealing with Iran, through dialogue rather than force, is not only driven by Russia’s economic interests in the region, but is also a dependent variable of the larger Russia–USA rivalry at the systemic level characterized by both geopolitical competitions and ideational contestations over norms, beliefs, and practices of global governance.