Analogical reasoning in law and foreign policy remains an area of contentious debate. Adherents to the practice of analogical reasoning have argued that though imperfect as a method, it builds on past decisions, and as explained by Ronald Dworkin in Law’s Empire, ‘it redescribes the traditional method of legal reasoning by analogy as a source of integrity’ (as cited in Sherwin). Pertaining to law, analogues serve an instrumental purpose, and allow for the preservation of its [law] evolutionary character (Sherwin, p. 1193). Critics, however, have argued that the approach is logically flawed and possibly incoherent. Pertaining to foreign policy, as Khong explained, “More often than not, decision makers invoke inappropriate analogues that not only fail to illuminate the new situation, but also mislead by emphasizing superficial and irrelevant parallels” (p. 12). Moreover, schema theorists have found that individuals hold on to the schemes even when confronted with contradictory information. Building on Khong’s explanation, I argue that the use of analogies in political organizing (not legal advocacy and organizing), more often than not does not serve its intended purpose. Pertaining to law, analogues serve an instrumental purpose, and allow for the preservation of its [law] evolutionary character (Sherwin, p. 1193). Pertaining to political organizing and the attainment of political settlements, however, since analogical reasoning requires putting new information into an existing template, it highlights the deficiencies of the application/comparison. Moreover, as Khong notes, schema theorists have found that individuals hold on to the schemes even when confronted with contradictory information. This paper will examine the analytic utility of such analogies, especially pertaining to the longer term impact on political organizing and policy formulation. Through careful historical analysis of a number of cases, especially the Palestinian territories, and Northern Ireland, this paper will assess the benefits of invoking various analogies as an instrument in political organizing. The paper will examine the unfolding political trajectory pertaining of the Israeli-Palestinian conflict, and current analogies now in vogue, and examine how the use of such analogies might help or hinder the formulation of political programs that endeavor to respond to current developments, especially the escalation of violence and human rights abuses against Palestinians, and the over-all deterioration in Palestinian quality life. This paper will rely primarily on historical literature that has addressed the various conflicts and related political movements under examination.