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The study of foreign policy, aid, development, and relations among nations tends to focus on policy choices. Yet the means of organizing a relationship among parties and the cultural brokers who serve as links among them can play a huge role in outcomes and even undermine policy objectives. The U.S.-Russia relationship that emerged during the 1990s in the service of U.S. economic policy and aid to Russia is one such example. A group associated with Harvard University representing the United States and the “Chubaï Clan” representing Russia carried out radical economic “reforms” in Russia and managed hundreds of millions of dollars in Western aid and loans. Working together, these transnational brokers developed a modus operandi of “transactorship”, a form of collusion between the representatives of parties on opposite sides. The influence and activities of the Harvard-Chubaï group ultimately undermined the stated objectives of U.S. assistance to Russia. Transactorship worked to frustrate true market reform, circumvent accountable and democratic institutions, and harm the bilateral relationship. This mode of organizing relationships, though unusual, is not new with this case. Although transactorship raises questions of accountability and participation, it likely will become more common because the circumstances that facilitate its emergence have become more prevalent in the international arena of retreated states and diffuse authority.