Perhaps no other issue so starkly lays out the fault lines between the idealistic and realistic strains in American foreign policy as does the subject of covert action. The title of this essay consciously reflects that of Gunnar Myrdal's classic study of race in America, "An American Dilemma." Myrdal posited, accurately, that the conflict between stated American ideals of freedom, democracy, and equal justice and the realities of race discrimination created a tension that America would inevitably have to address. Beginning with World War II and Franklin Roosevelt's fascination with General "Wild Bill" Donovan and the Office of Strategic Services (OSS), U.S. leaders have seen covert action as an attractive tool for a dangerous world. Many proponents of covert action justify its use in "realist" terms. While the author does not detail them in this paper, there are strong arguments for using covert action, especially when carried out as part of an agreed-upon public policy and with adequate oversight and review. Generally, these arguments focus on two elements: necessity (i.e., extreme threats call for extreme responses) and effectiveness (i.e., some things can only be done covertly). However, neither of these arguments addresses the heart of the issue: that covert action is basically antithetical to the values that the United States espouses and to the policies that it would like other countries to adopt. In a society that fundamentally adheres to democratic ideals, covert action, by its very nature, creates a basic conflict. After first detailing why this is so, particularly for the United States, this paper will examine the continuing consequences of the use of covert action on the United States, on the image of its citizens as Americans, and on its role in the world.