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How do digital platforms justify profit-making from speculation? While existing research argues that companies secure legitimacy by arranging political-economic conditions and mobilizing moral claims, digital platforms represent a unique and rapidly shifting case. They embed speculative logics within opaque technological infrastructures that enable hitherto unimaginable forms of direct consumer engagement. This paper analyzes the United States’ online sports betting market to assess how different digital speculation platforms justify profits. Drawing on 52 in-depth interviews with operators, regulators, and media professionals, I identify a central tension among operator types rooted in differing framings of the user’s relationship to speculation. Three operator types advance three distinct frames: (1) traditional sportsbooks encourage and engage expert and lay bettors alike and use expert participation for efficient odds-making; (2) digitally-native platforms position betting as mass-market entertainment, using computerized odds and risky products to increase profit margins; and (3) insurgent prediction markets invoke investor-style forecasting logics to justify financial-market-like trading fees. These frames imply particular responses to three elements of the speculation business: risk estimation, risk distribution, and risk packaging. Operators concretize these frames through pricing strategies, platform designs, and regulatory engagement, and advance frames in legal, financial, and popular arenas to secure legitimacy. By mapping these competing justifications, this study demonstrates how online sports betting serves as a critical site for viewing broader shifts in popular digital engagement, ranging from social media to retail stock investing.