W.E.B Du Bois is arguably the most famous African-American scholar and political activists of the Twentieth century. Despite a resurgence of academic interest in Du Bois’ expansive body work in recent decades, it remains a little known fact that this anti-racism crusader spent five-months in Hitler’s Capital in 1936, which happened to have coincided with Jesse Owen’s heroic performance at the notorious “Nazi Olympics.” Although Du Bois published a weekly column in the Pittsburgh Courier throughout his five-months sojourn in Nazi Germany in 1936, he had to keep silent about what he really saw there. As soon as he left the Nazi state, however, he broke his silence on Hitler’s totalitarian regime and anti-Semitism, in a series of five weekly columns. This paper will focus on this series of columns, written about Nazi Germany, and published immediately following Du Bois’ departure from it. My research question is how does Du Bois describe Anti-Semitism in Germany to his African-American readers? And how does his analysis of Anti-Semitism help us to better understand Du Bois’ comprehension of racial-antagonism as a general social phenomenon, when he faced with a peculiar case study in which victim and perpetrator are on the same side of the color-line. While a few scholars mentioned in brief Du Bois’ palpable outrage by what he had witnessed in Berlin, a close reading reveals his struggle to explain, or even fully comprehend, race prejudice that does not cross the color-line. Wavering between comparing German-Jews’ predicament to that of African-Americans’, and claiming that the situations are “not at all analogous,” Du Bois’ analysis is replete with contradictions, gaps, and slippages. His ambiguous position is aptly summed up by his claim that “race prejudice in Germany…is not instinctive prejudice, except in the case of the Jews, and not altogether there…It is reasoned prejudice, or an economic fear.” But could there really be such a thing as ‘reasoned prejudice’? I argue that this oxymoron lies at the core of Du Bois’ ultimate failure to analyze Nazi Anti-Semitism, which stemmed from his inability to fully comprehend race prejudice that is not marked by skin color. I will prove my argument by performing a close-reading of Du Bois’ 1936 columns about Germany, focusing specifically on his third column, which was devoted in its entirety to Anti-Semitism. I will point out the contradictions between Du Bois’ explicit assertion that Nazi Anti-Semitism and American Anti-Blackness are qualitatively different, and the implicit message that slips between the cracks of his language, that the two are essentially similar. I will also use other texts written by Du Bois around the same time as an aid to decode some of the terms he uses, which will further underscore the incompatibility of his analysis of Anti-Semitism with his own understanding of race and race prejudice at large.