Seven previously featured "Bosses" discuss the challenges they had with keeping their identity undercover. Also, they provide updates on some of their memorable employees.

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.