This article situates the recent explosion of online and app-based sports betting within longer histories of datafication and financialization in sports business and culture. The author tracks four histories in which media technologies and financial logics dissolved previously stable sporting events, athletes, and results into aggregations of data and derivatives that could be leveraged and wagered on. Photography established feelings of confidence and objectivity in horse-race results during the nineteenth and early twentieth centuries. Screen and computational technologies since the 1970s have enabled Las Vegas casino sportsbooks to overwhelm bettors with data abundance. Television and web-based play moved poker at the turn of the millennium away from surprise, chance, and reading people toward probability, risk, and reading data. Around the same time, fantasy sports and management-based video games mirrored financial markets in transforming athletes and leagues into derivatives, that is, disaggregated units that could be reassembled in new digital permutations. Each story helps position contemporary online sports betting within a longer historical arc in which gambling and speculation moved to the center of global economy and culture.

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