Scene 5 shifts back to the present. Willy goes to Charley's office where the secretary, Jenny, overhears him talking to himself. Willy is still enjoying his reverie from Scene 4. Willy is taunting someone about Biff's impending football game and the touchdown he has promised to make for Willy. Willy's daydream ends when he sees Bernard. Willy discovers that Bernard is very successful and that he will soon be staying with rich friends who have their own tennis courts. Willy tells Bernard that Biff is closing a business venture with Bill Oliver. Willy also states that Oliver recruited Biff and is paying his expenses.
Willy asks Bernard how he managed to succeed so well, while Biff did so poorly. According to Willy, Biff's life took a turn for the worse after the Ebbet's Field game. Bernard reminds Willy that Biff failed math, and as a result, he did not graduate. Bernard questions why Biff did not attend summer school. Willy is not sure why he did not go.
Bernard remembers that Biff traveled to Boston to visit Willy and talk about his future. He then tells Willy that Biff burned his homemade University of Virginia tennis shoes and got into a fistfight with him when he returned. Bernard asks Willy what happened to Biff in Boston. At this point, Willy becomes angry and resentful.
