Ben appears in one of Willy’s imagined conversations. He is in a rush to catch a train and repeatedly urges Willy to go with him to Alaska.
Questioned by Willy, Ben explains that he tried to follow their father to Alaska, but somehow ended up in Africa. Despite missing his intended continent, he struck it big in diamond mines.
Ben insists he has to leave, but tells Willy that their father used to play the flute. Their father also drove the two of them around the country by wagon and sold his inventions along the way.
Willy wants to prove how great his sons are, and gets Biff and Ben to fistfight. Ben wins the fight by cheating, and tells Biff never to fight clean with a stranger.
Everyone leaves the stage except Ben and Willy. Willy confesses that he’s scared that he might have not done such an amazing job of raising his sons; he begs his brother to stay. Ben insists he’s got to run and leaves the stage.
The following day, Ben appears in another of Willy’s fantasies. Again, Ben asks Willy to join him in Alaska.
Willy brags to Ben that his sons can succeed solely on the basis of being attractive and well-liked. Struck by another wave of self-doubt, Willy begs Ben to remain and help him with the boys. He feels unsure of himself. But again, Ben leaves.
That night, Willy daydreams about Ben again. Willy is bouncing ideas off of his brother. He’s thinking about what he can do to get Biff to be successful. His thoughts turn to the life insurance payout of $20,000, which could really get his son started in business. Imagining his own funeral, Willy tells Ben it will teach Biff once and for all how well-known and liked his father is.
Ben responds that it’s a cowardly idea.
After the big fight with his son, Willy imagines Ben repeatedly saying, "the jungle is dark but full of diamonds," and that Biff could be great with $20,000 behind him.