This chapter analyses how complex litigant configurations relate to legal success and policy and institutional outcomes. In the first section, the chapter revisits the literature on litigant constellations by carving out the relevant approaches and interpretations. This will provide orientation for analysing empirical patterns of complex constellations as identified by our statistical exploration. In the second section, we spell out our argument based on an endogenous conception of litigant configuration and legal uncertainty, which provides an innovative explanation to the relationship between complex litigants' configuration and judicial success. In a third section, we identify an additional causal mechanism driving the relation between complex litigants' configurations, legal uncertainty, and judicial success based on the heterogeneity of legal arguments presented to the Court. We then analyse empirical patterns of litigant's configuration and judicial success, which give support to our argument about the endogenous relationship between legal uncertainty, litigants' configuration, and judicial success. Finally, we close the sequence linking policy conflict to litigation, to litigants' configurations, and to ruling outcome by turning to the distributive effects of annulments rulings on policy stakeholders. Taking into account the objective that motivated the litigant to turn to court in the first place, we find that, although winning-the achievement of the litigant's primary objective-is generally associated with judicial success, in many cases, winning and judicial success are disconnected.