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Since a 2018 Supreme Court decision overturned a 30-year federal ban on sports betting, 38 states have legalized the practice, with most betting occurring digitally. This rapid expansion has sparked debates among stakeholders—including sportsbooks, state officials, prominent bettors, and mental health professionals—about the legality, morality, and legitimacy of digital sports betting. I identify two key features that set digital sports betting apart from other gambling products: its speculative nature and digital accessibility. These distinctions complicate direct comparisons to other forms of gambling and similar consumer experiences/products, prompting ongoing debates about how to conceptualize, legitimate, and regulate the practice. Over the past five months, I have collected interviews, ethnographic fieldnotes, and professional documents from national and Illinois-based stakeholders, as well as interviews and surveys from engaged bettors. Using institutional analysis for stakeholders and cultural analysis for bettors, I identify and examine two central conflicts in the industry: whether betting is a form of entertainment or investment and how bettors navigate the instant digital access that heightens betting’s appeal. I explore how stakeholders and bettors define the emotional experience of betting to navigate these conflicts, shaping broader debates over regulation and market structure. This study offers insights into a pressing social issue while contributing to research on market formation and the digital economy. This manuscript presents a preliminary analysis of my data, with data collection and analysis expected to be completed by July.