This article presents Azerbaijan, a post-Soviet state known for its oil and gas wealth, as subject to misconceptions by the West. The author explains three elemental tendencies that accentuate the pivotal nature of Azerbaijan’s geographic position: infused with Iranian culture, ethnically and linguistically Turkic, and historically part of the Russian, then Soviet empires. Eurasia’s future is likely to play out in and around Azerbaijan for reasons that are independent of the Caspian’s energy wealth but are amplified by it. Further, the author looks at Azerbaijan’s neighborhood, and examines its geopolitical position, concluding that investment and trade between Azerbaijan and Turkey - while promising - should not come at the expense of further regional integration, given the relative decline of the West versus the rise of the East in the 21st century. The desire for 360 degrees of “strategic depth” in both Ankara and Baku reflect pragmatic calculations and hedging about Western commitments to the region. Tracing developments in Azerbaijan’s near-abroad, starting with Turkey and its traditional Western allies in America and Europe, then moving to its neighbors in the post-Soviet space and the Middle East, this piece outlines the global changes in geopolitics, economy, and energy that have presented Baku with complex challenges as well as opportunities.