Nikolai Vladimirovich Timoféeff-Ressovsky was one of the key figures in the Synthetic Theory of Evolution. Living and researching under what was arguably the two most powerful and cruel totalitarian regimes in human history, the Third Reich and the Soviet Union, Timoféeff-Ressovsky succeeded in developing an ambitious research program aiming to explain evolution on all major levels, from the molecular-genetic, the populational, and the biogeocenotic to the level of the entire Biosphere. Yet his scientific biography remains largely unwritten and his role under totalitarianism, especially in Nazi Germany, remains highly controversial. Here we approach the problem of his hypothetical cooperation with Nazi authorities examining both the crucial episodes of his biography and summarizing the development of his research program. We conclude that the key decisions he made reflected the specificity of his research program that was focused on the fundamental questions of evolutionary biology.