Prior to the overthrow of Saddam Hussein, Moscow historically enjoyed close political and economic ties with Iraq. During this time, Iran was a bitter rival of Hussein’s regime. However, since the full-scale war in Ukraine, Russia has established close relations with Tehran. Drawing from governmental statements, news media, and think tank reports, this paper examines how the Kremlin’s foreign policy pivoted away from Iraq and towards Iran over the last two decades. How did Russia overcome its history with Iraq in forging ties with Iran? To what extent has this pivot allowed Moscow to reassert its influence in the Middle East?