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In Death of a Salesman Willy Loman and his father do not really resolve any of their issues. Instead, Willy's father simply leaves the household when Willy is very young. Eventually, so does Willy's brother, Ben. Both men did the same thing and for the same reason. They were tired of their current situation, so they left everything (even family) behind to try their luck at a huge endeavour.
We know that the loss of his father at such a young age really does leave a huge gap in Willy Loman's development. The lack of a supportive male figure created black holes in Willy's own personality, which is what may have likely led him to be a less than stellar parent himself.
Yet, part of Willy's need to overcompensate with his children (to the point of spoiling and stunting them) has a lot to do with Willy's pining for a father figure. He never stopped loving his father and, rather than demonize him, he continuously remembers him with love- and even admiration- that he had the courage that Willy tremendously lacks.
Father was a very great and wild-hearted man. We would start in Boston, and he’d toss the whole family into the wagon, and then he’d drive the team right across the country: [...] And we’d stop in the towns and sell flutes that he’d make on the way. Great inventor, Father.
Willy's father was a salesman too, but he had creativity and, clearly, a mission in mind to make something different happen. Ben had courage, and a knack for making money. All these things seem to miss out in Willy.
When I was a boy[...] there was a question in my mind as to whether selling had a future for me [...] I had a yearning to go to Alaska . . . my father lived many years in Alaska. He was an adventurous man.
What is there for Willy to do? He finds a father figure, or a surrogate one at that, in the character of Dave Singleman.
I thought I’d go out with my older brother and try to locate [Willy's father] and maybe settle in the North with the old man. And I was almost decided to go when I met a salesman in the Parker House. His name was Dave Singleman. And he was eighty-four years old, and he’d drummed merchandise in thirty-one states.
The elderly and seemingly eccentric salesman was successful without much effort. He found the proverbial shortcut to success, and Willy liked that. That is his tragic flaw: contrary to his father and brother, he did not want to walk the road less traveled; he wanted the shortcut. Therefore, Willy tries to make up for the lost time trying to overcome his fear to take risks by desperately trying to get a way to reach the goals of his father with little effort.
Unfortunately for Willy, this is never going to be the case. He dies a fatherless father whose legacy is a mere life insurance that may or may not pull out his own two children from the sad reality in which they all lived: that they had fantasized their lives and have been in search of a futile and non-existent American Dream. Therefore, the chain of chaos may continue among the Lomans unless the two surviving men, Biff and Happy seriously take a look into their own lives and break their vicious cycles.
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