Sometimes a work of art with no immediately apparent connection to political conflict can disguise a powerful statement relevant to the vicissitudes of war. This situation can arise in portraiture, which can be more than merely the record of a meeting between the artist and the sitter.  In 1925, while Adolf Hitler was still all but unknown to the German people, the artist Otto Dix (1891-1969) produced an image of a friend, the Jewish lawyer Hugo Simons (1892-1958). This thesis will examine the painting and how the harrowing story of racism, propaganda and censorship under the Nazi regime is embedded in the image.  Chapter One will look at the career of Dix and the developments in his life and artistic training, as well as his work as a founding member of the neue Sachlichkeit art movement. It was during his involvement with this group that the portrait was painted. Chapter Two will focus on the professional relationship that formed between Dix and Simons in 1920s Düsseldorf. Chapter Three will deal with the politics and social conditions of 1920s-1930s Germany, the rise of Nazism during this period and the implementation of discriminatory cultural laws and racist aesthetics. Chapter Four chronicles the Simons family's flight from Nazi Germany, and the long-standing friendship of the two men is shown through letters written to Hugo Simons from Otto Dix after the Simons family settled in Canada in 1939. Finally, Chapter Five looks at the portrait's 'rediscovery' by curators and art historians in 1991, and the saga of its acquisition by the MBAM