In 1925, Hugo Simons won a lawsuit on Dix's behalf. The artist painted his portrait in a display of gratitude. He generally preferred to accentuate a subject's ungainly characteristics but this depiction was almost flattering. The pair maintained a friendship for the rest of their lives. When the Nuremberg Laws stripped him of citizenship, Simons fled Germany for Canada. He died in Montreal with Dix's portrait hanging on the wall opposite his bed.