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This paper will look at the legal situations presented by the newest advertising category that could keep broadcasters in the black, but may leave their audiences in the red. Americans, their governments, and gambling have had a rocky relationship that predates the nation’s founding. A series of federal and state laws prohibited or permitted various forms of betting as well as punished or allowed promotion of gambling. Some of those laws have been challenged under the First or Tenth Amendments by broadcasters or lower governments. This study will review the impact of three of these challenges: federal laws and regulations that prohibited lottery advertising, casino advertising, and especially, gambling on sporting events. The desire for sportsbook operators to find new customers and the industry need to make up for revenue lost during the COVID-19 pandemic recession created advertising and programming that went almost overnight from illegal to vital. It will be shown that while broadcasters need this new revenue category, there are myriad legal and ethical concerns.