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The questions when, why, and how legal representation makes a difference for parties in civil litigation remain largely unanswered, although recent scholarship raises compelling new questions and suggests new explanations and theoretical approaches. Understanding how legal representation operates, we argue, requires an appreciation for the context in which the representation actually takes place. This article examines two previously unexplored elements of the context of legal representation through empirical and theoretical analysis: the balance of power between the parties to a dispute and the professional, specifically strategic, expertise that a legal representative contributes. The results of a study of 1,700 unemployment compensation cases in the District of Columbia’s central administrative court reveal two key findings. First, represented parties have better case outcomes than unrepresented parties, though employers–-the more powerful party to a dispute or the quintessential “haves”-–see less benefit from legal representation than claimants–-the less powerful party or the “have nots.” Second, represented parties are more likely to use procedures than unrepresented parties. Yet, surprisingly, represented claimants who use certain evidentiary procedures have worse case outcomes than represented claimants who do not use those same procedures. Thus, in attempting to answer the question of when, why, and how legal representation makes a difference, we argue that it depends on who the represented party is, who they are up against, and the expertise the representative brings.