On July 22, 2022, Ukraine, the Russian Federation, Türkiye, and the United Nations signed a groundbreaking agreement to allow for the safe transport of grain, related foodstuffs, and fertilizer from three Ukrainian ports to global markets. Concurrently, a second (lesser known) agreement was concluded between the United Nations and Russia that would allow the unimpeded export of Russian food and fertilizer (including raw materials to produce fertilizers) to world markets. These agreements were hailed as a critical solution for the impending global food crisis and the safety and security of neutral shipping in the Black Sea resulting from the Russia-Ukraine war. One year later, the question remains—what motivated Russia to agree to the deal? This article evaluates whether Russia’s decision to support the UN Grain Deal (and its two subsequent renewals) was a strategic blunder or a well-informed diplomatic coup.