Fedor Stepun was a kind of a bridge between the German and Russian cultures. Stepun’s cooperation with the Catholic magazine “Hochland”, in which he published a number of articles after his expulsion from Soviet Russia in 1922, played a special role in this regard. The first section of the essay includes the analysis of the articles in which Stepun tried to explain what had happened to Russia after the overthrow of the czar and after the collapse of the fragile Russian democracy that had been created in February, 1917, to German readers. Although Stepun was ready to recognize a significant share of the Russian tragedy that began in October 1917 was the responsibility of the Russian democrats, he strongly rejected the widespread thesis among Russian emigrants that the democrats were “the only ones to blame for all the horrors of the current state of Russia”. The next topic of Stepun’s articles published in the magazine “Hochland” in the 1920s was the analysis of the Bolshevik regime, the first totalitarian regime in modern history. The second part of this essay analyzes Stepun’s articles which appeared in the magazine “Hochland” after Hitler came to power in January, 1933. As one of the last bastions of “half-free speech” in Nazi Germany, the magazine “Hochland”, granted Stepun, who remained a convinced democrat, the opportunity to publish his articles even after 1933. Although these articles were devoted to Russian subjects as a rule, they also contained criticism of the German order of that time between the lines.