This study draws on complexity theory to critically explore the law’s perception of success as a reliable indicator for intrinsic qualities. The perception of success-as-a-proxy underlies fundamental legal notions—from the market as an ‘aggregation of preferences’ to the ‘marketplace of ideas’ as an arbiter of truth—and affects myriad doctrines deriving therefrom. Drawing on cutting-edge research in complexity, the inquiry reveals that the conventional legal account of success is often misguided. It clarifies that the relations between success and quality are inherently nonlinear, that network dynamics can lead to significant discrepancies between success and intrinsic qualities, particularly with respect to the ultra-successful, and that the linkage between quality and success is weakening in digital, interconnected environments. Against this analysis, the article proposes a roadmap for embedding a nuanced, complexity-informed, understanding of success within legal frameworks, to better align the law with the social goals it seeks to promote.