He had to at least give it a shot. If there was a power that would let both him and Brett could stay this week, it was worth a try. Winston was a salesman, after all. But Sam's not the easiest customer to sell to, and it'll take a lot more than shiny words to win her over. Takes place on the night of the Week 3 eviction, if Winston did end up confronting Sam about her power like he wanted to.