It is extremely common for American parents to want their children to be successful. Part of the American Dream is for people to have children who are better than their parents--better educated, better looking, more intelligent, and especially better off financially. Bernard symbolizes all that. He has wealthy, important friends. He plays tennis on their private courts. He is going to argue a case before the U.S. Supreme Court! Willy has begun to realize that he is never going to amount to much. Like a lot of other fathers, he consoles himself that at least he has been biologically successful. He has fathered two strong and healthy sons and worked hard to raise them to manhood. They could salvage his American Dream--but only if they are successful themselves. Willy has pinned his hopes on Biff, since Biff seemed to show the most potential. He has tried to condition Biff to be ambitious and enterprising. And Biff has tried to live up to his father's expectations. But he can't make it. He doesn't have any special ability. He didn't get any specialized training in school. At the very least he could have gone to college and learned a suitable profession or trade. He could never have been a doctor and probably wouldn't have made a good lawyer, but he could have become some sort of draftsman or medical technician or a contractor or something along those lines. For some reason, he didn't prepare. A high school diploma won't take you very far these days, and it wasn't too much better in 1949. The natural profession for Biff to go into with his limited education and average intelligence was selling. But he is athletic, physical, an outdoors man. He might have made a good forest ranger. He doesn't like selling and he hates the business world. He begins to realize that Willy had been trying to push him in the wrong direction to satisfy Willy's ambition and not his own. Finally he rebels. Willy believes that Biff is just ungrateful, possibly lazy, spiteful, vindictive. Willy secretly suspects that Biff has never forgiven him for that incident in Boston when Biff caught him in a hotel room with a half-dressed floozie--but that is probably not the case, just Willy's guilty conscience and fear that Biff has something on him which he might use against him. After all, Biff is a man of the world. He has had plenty of affairs with women and shouldn't take such an incident all that seriously. Biff's basic problem is that he loves his father and wants to please him but can't change into someone he is not. He tells his father, "I'm a dime a dozen!" This confrontation between father and son may be fatal to Willy, but it is Biff's salvation. He can go out West and work outdoors doing the kind of thing he is really suited for. Willy can never change. He is used up, worn out, ready for the ash can. The American Dream, according to Arthur Miller, not only brings tragedy to the dreamer but to those associated with him. 

Death of a Salesman by Arthur Miller examines the “American dream.” In the 1940s, the dream was basically the same as it is today: have a happy, healthy family, be successful, and be able to buy whatever a person wants.  Willy Loman wanted all of those things; however, he did not know how to get them.  His perception was completely wrong.  Unfortunately for his sons, Willy had instilled the same view in them.  Now, they are not successful either. 

Willy’s son Biff had the potential to be a big success.  He had two of the facets that Willy believed were necessary to be a winner: attractiveness and popularity. Biff had been a great football player in high school with several scholarships to go to college.  Yet, Biff missed out on them because he failed a math class.

Why is Willy mad at Biff? Biff has just returned home from working as a farmhand in the West. He thinks Biff could easily be rich and successful but is wasting his talents and needs to get back on track. Willy is upset because Biff has not been able to hold down a job that is similar to Willy’s job where a man wears a suit and works in an office.

Even though Willy’s failure has handicapped him his adult life, now Biff has let him down. Willy  has tried to live vicariously through Biff, who was unwilling to carry his father on his back.  Willy decides that Biff is lazy and wasting his life to spite his father.

WILLY: Don’t you want to be anything?

BIFF: Pop, how can I go back?

WILLY: You don’t want to be anything, is that what’s behind it?

WILLY: Are you spiting me?

BIFF: Don’t take it that way!

WILLY [strikes Biff and falters away from the table]: You rotten little louse! Are you spiting me?

Biff could have gone on with his life and college if he had taken a summer course.  Every step of the way, Willy has enabled Biff to do the immature or foolish thing in his choices. 

When Biff finds out that Willy has been cheating on Linda, Biff essentially goes off the deep end. From there, he spiraled downward. He started working on ranches in the West; yet, he could not hold a job because he kept stealing from his bosses. Finally, he realizes that he is 34 years old with nothing important in his life, and his father is partly to blame. 

Biff is the most sensitive character in the story. He loves his father and mother.  Flawed just like every person is, he wants to change and find happiness, and he is caught us trying to impress his father.  Unlike his father, Biff values the truth and wants acceptance for who he is.  The other members of the family consistently lie to the others in an effort to keep from having any confrontations; on the other hand, Biff recognizes that he wants to escape the cycle of lying and stealing.

Even though, Biff tells Willy that he does not want to be a salesman and that he does not want his money, Willy is too far gone to listen.  He is hallucinating and living in his version of the world.  He thinks the greatest contribution that he himself can make toward his son’s success is to commit suicide. That way, Biff could use the life insurance money to start a business.

When Willy decides that he will leave the insurance money for Biff to become successful, he kills himself in a car accident.  But even in death, Willy is not successful because the insurance will not pay if there is a suicide involved.