Through the U.S. Lend-Lease program, President Franklin D. Roosevelt sought to keep Joseph Stalin's Red Army fighting Adolf Hitler's forces to prevent a separate peace and Nazi Germany's colonization of Soviet territory and strategic resources during the Second World War. Yet after the Red Army's 1943 counterattacks, Roosevelt unnecessarily increased Soviet Lend-Lease aid, oversupplying Stalin's soldiers with more armament than they required for the Soviet Union's defense and enabling their subsequent conquest of East Central Europe and large parts of East Asia. Roosevelt's underestimation of the Red Army's capabilities, his tendency to readily rely on Soviet-influenced advisers, and his unquestioning acceptance of Stalin's implicit threats to forge a separate peace all contributed to his excessive arming of Moscow from 1943 forward. Expanding on the findings of other scholars, this work identifies and explains the impact of the Brest-Litovsk Treaty on Roosevelt's reasoning, the key role of the Arctic convoys in delivering material to the Red Army, and how the unnecessary aid routes through Iran and Alaska resulted in the oversupplying of Stalin's troops. Had Roosevelt not opened these unnecessary routes, the Arctic convoys could have continued to sufficiently supply the Red Army's defensive efforts without empowering it to aggressively spread Communism at gunpoint.