For hundreds of years, gambling has been defined by three elements: consideration, chance, and prize. In recent years, this foundational framework has become increasingly difficult to apply to innovative commercial activities, which look a lot like gambling to a casual observer. This Article discusses an emerging trend by entrepreneurs to structure games in a way that, despite having gambling-like elements, appear to fall outside of the reach of regulators. The Article examines the challenges that regulators and law enforcement have had applying the three elements to video-game loot boxes, daily fantasy sports, and sweepstakes casinos. The crux of the Article is that the three-element test, as historically constructed, is too vulnerable to exploitation by innovators who seek to avoid regulation (and in some cases taxation). The Article concludes that while it is worth reexamining the historical definitions of what constitutes gambling, any meaningful legislative changes must be accompanied by increased enforcement, or the legislative changes will be strictly performative.