This scene returns to the present. Here, Willy goes to Charley's office to pick up the money that he regularly borrows from his neighbor. Getting off the elevator, he sees Charley's son, Bernard, who is now an adult and a high-class lawyer (in fact he is currently arguing a case before the Supreme Court).
Bernard begins a conversation with Willy, asking the fired salesman about Biff. At first Willy pretends that "big things" are happening to his son as well, seeing that Bernard is so successful. Later, though, Willy admits that Biff has failed and asks Bernard where he went wrong in raising him. It seems that after the Ebbets Field game, Biff's career as a football player was over (Miller only briefly alludes to this point). Bernard doesn't know why Biff gave up, only saying that one day Biff went to Boston to visit Willy on the road. After this incident, Biff apparently lost all desire to go to summer school and graduate. Bernard asks the salesman about Biff's trip: "I've often thought of how strange it was that I knew he'd given up his life. What happened in Boston, Willy?" This causes Willy to grow uncomfortable, for though the reader doesn't know it yet, Biff caught Willy with a prostitute in Boston.
Finally, Charley enters the scene, telling his son that he's going to be late for his train. Bernard exits, leaving Willy and Charley alone. Charley willingly agrees to lend Willy whatever cash he needs to pay his insurance, but he also offers his neighbor a job with the firm. Willy is stubborn, however, and tells Charley that he won't work for him. It seems Willy is too prideful to take a job from his neighbor. Though he is willing to "borrow" money from Charley, accepting a job from his kind friend is going too far.
At the end of the scene, Willy alludes to suicide. He admits to Charley, "After all the highways, and the trains, and the appointments, and the years, you end up worth more dead than alive." It seems Willy has a sizable amount of life insurance.