The love/hate relationship between Willy and Biff stems from three events that changed the perception that the men had of one another:
- uncovering who each of them really is
- ending their sham dynamics and
- realizing the difference between their fantasies versus their reality.
Willy saw in Biff both his future dreams and his shattered dreams. Biff was the source of Willy's hopes and possibilities. When Biff was no longer Willy's symbol of success, Willy's former admiration transformed into rejection. All is further complicated by the fact that, regardless of it all, they are still father and son.
How it all began
From the very beginning of the play Death of a Salesman, the audience can perceive that there is an inner conflict between the character of Willy Loman and both of his children. This becomes evident when Biff tells his brother Happy about his father, Willy:
"Everything I say there's a twist of mockery on his face. I can't get near him."
The problem between Willy and Biff started when the latter was 17. Willy adored Biff, who had grown up to become a good-looking, tall, athletic, and witty teenager. Willy relished basking in the light of his very popular son, who represented everything that Willy believed in. He saw in Biff someone who, at a very early age, had accomplished the earmarks of the American Dream, according to Willy.
Biff was
- well-liked
- popular
- admired
- handsome
- successful
Willy loved so much to vicariously mesh himself into Biff's persona that he transferred all of his views of life, and of himself, onto his son: In Willy's eyes, Biff was basically a better, perfected, much more successful version of himself.
In turn, Biff loved and admired his father; at least, he admired the version of his father that Willy presented to him--someone who is also well-liked and very successful.
However, all of this imagery and mutual admiration was over once Biff discovered that Willy cheated on Linda, Biff's mother. His view of his father, and the persona of the fatherly hero that Biff once held so true, shattered him enormously. As such, he refused to continue being a part of the dyad that once were Willy and Biff. Biff goes away, leads an unsuccessful and unfulfilling life, and becomes everything that Willy feared and dreaded.
As such, Willy now sees Biff as a defector, or a traitor, of what could have been a great alliance. Biff is a failure of the American Dream. He is no different than Willy--the difference is that Willy insists on living in a fantasy world.
Willy has an unhealthy type of fixation with success; one which is entirely shallow and superficial. Hence, rather than exploring ways to mend the relationship with Biff and see how his son could be happier, he rejects Biff's lifestyle and takes it as a direct attack on his own dreams.