Despite a few short periods of smooth cooperation, misperceptions and divergences between Russia and the West have widened since the collapse of the Soviet Union. Some of the most relevant problems in their relationship will be briefly mentioned here below and some are not new in their essence. Unquestionably however, the Ukrainian crisis has exacerbated the confrontation. As a reaction to the annexation of Crimea and the war in eastern Ukraine, the US/EU sanctions against Moscow, Russia’s exclusion from the G8, the strengthened military presence of NATO on Russia’s borders (particularly in the Baltic republics and Poland) and the different ideas of modernization in terms of global governance promoted by the West are just but a few examples of a set of adopted measures aimed at challenging and marginalizing the international role of Russia. Nevertheless, the Ukraine crisis and its aftermath has occurred in a broader and disorderly context, marked by declining US world authority, growing cacophony in the EU, and the rise of different global players. These circumstances are posing the Kremlin not only with challenges, but also opportunities to avoid marginalization and reshape its external role, by juxtaposing a multilayered network of international organizations on to traditional western-centric policy. And in fact, Russian diplomacy has engaged in a pragmatic strategy which encompasses both the Eurasian and Euro-Pacific dimensions, while stimulating the search for a global identity profile. In view of these considerations, and with the aim of understanding Russia’s self-perception of its world role, this chapter investigates the most relevant obstacles and potential that Putin’s foreign policy is facing in his effort to redefine Russia’s place as a recognized great Power in a still disorderly and fluid world . The chapter is therefore structured in three main parts, focusing respectively on (1) the roots of Russia’s disappointment with the West, (2) efforts to design a global strategy of multiple networks, with Russia playing a key role, and (3) the endeavour to construct an attractive, worldwide cultural identity of Russianness.