Bruce "Two Dogs" Bozsum, Chairman of Mohegan Sun, goes undercover in the gaming, hotel and entertainment destinations as he prepares to pass the business on to the next Chairman of his Native American Tribal Council. Bozsum learns the high-stakes role of slot attending and nearly runs out of gas as he retrieves cars from the valet.

Greg Miller, CEO of the Utah Jazz, one of the most recognizable basketball organizations in the NBA, attempts to make halftime history when he works undercover with their infamous Dunk Team. Also, the boss' team spirit is put to the test when he is asked to become a human basketball hoop as a member of the Interactive Team.