The prominence of the Iraqi Communist Party during the 1950s, and thus the greater susceptibility of Iraqis to the “dangers of Soviet imperialism”, made Iraq a target of CIA intervention. One face of that intervention was a cultural organization, the American Friends of the Middle East (AFME), a group of purportedly private citizens who sought to nurture a species of cultural “Arabism” in the arts. The AFME supported Iraqi artists by exhibiting and purchasing their work. Thus, in 1954, Iraq’s most famous artist, Jawad Salim, was exhibited at a space run by the AFME on Michigan Avenue in Chicago. This paper attempts to understand the relationship between modern art in Iraq and the politics of the Cold War by looking at one painting acquired by the AFME, a 1955 painting by the Communist artist Mahmud Sabri entitled Sarifa Dwellers. The paper shows that the painting supported by the AFME functioned precisely as the mode of radical social critique that the AFME aimed to curtail. Sarifa Dwellers brought to visibility the economic issues that comprised the political agenda of the Communist Party; however composed in paint, in bright colors, the political content of the painting was veiled as ‘art’. The artwork could equivocate between its aesthetic and intelligible natures; it was by dissimulating as ‘art’ that it could intervene in politics. Thus was the modern art then developing in Iraq interpellated by the cultural politics of the Cold War, and thus did it exceed those politics, drawing nourishment from a form of support that was neither market-based nor state-sponsored, but without falling into the hands of one side or the other.