Why does the realization of Willy's (American) Dream ultimately fail? Or: How exactly do Willy's flaws cause his dream to not be executed?
Please explain exactly what makes his dreams impossible to be fulfilled.
There is one other part of the American Dream that is involved in the play, the belief that we still live in a world where the personal relationship between individuals in business is important. This may once have been true in a more rural America (Willie's one time garden now surrounded and boxed in by apartments, is a constant reminder of this). Willie never seemed to grasp the fact that profit had taken over any relational component in business. Of course, there may never have been such a component; it's impossible to tell if any of the friends that Willie thinks were part of his past were ever real.
At one point in the play he makes an interesting statement: "You can't eat an orange then throw the peel away --- a man is not a piece of fruit." There are two problems here. For one, the comparison makes no sense --- what are you supposed to do with the peel if you don't throw it away? In the world we live in, where utility may be the only value in human relationship, throwing away the peel is the rule, not the exception. But the real problem is that Willie really BELIEVES a man never really becomes a peel. He is as much an anacronism in his world as is his garden.
He may not be the victim though; the American Dream may be the real victim.
These are really two distinct questions. First of all, Willy Loman does not realize the American Dream, and as Miller so cleverly points out, even if one gains material wealth, it is still just a dream, not real, as possessions are only things. However, in Willy's case he is a double failure: as Biff says in Requiem, his father,Willy,followed the wrong dream, a dream for wealth and material goods. Not only that, but Willy did not even succeed in achieving the American Dream; it only led him to despair, and ultimately, his suicide so his wife, Linda, could pay off the house. Your second question leads to Willy's flaws which are also part of his charm (an essential characteristic of a tragic hero). Willy wants to reconnect with the land, thus the garden motif, to plant something, to have it grow, to be rewarded by his own labor unlike a salesman who sells a product of someone else's labor. Willy's weakness lies in his personality; he realizes there is more than the American Dream, yet he becomes trapped (as most of us) in seeking something that will ultimately destroy him. His son, Biff, stronger than his father, will seek to reconnect with the land as he realizes the Dream is merely a trap that only leads to emptiness. I would also suggest you pay close attention to when the flute is heard and its relationship to Willy-