Willy Loman has mixed feelings about his oldest son, Biff. As an adolescent, Willy hoped to live vicariously through Biff and believed that he could succeed at becoming a successful, wealthy salesman because of his appearance and likability. Tragically, Biff discovered his father having an affair during a business trip in Boston, which ruined their relationship. After discovering that Willy was cheating on Linda, Biff never tried to pass his math course or become a college athlete.
As an adult, Biff struggles to make ends meet and has not lived up to his father’s expectations. Biff’s failures in life make Willy upset, and he believes his son is unsuccessful out of spite. Willy cannot comprehend why Biff would not succeed, refuses to take responsibility for his son’s lack of success, and continually argues with Biff. Essentially, Willy places unfair expectations on Biff and refuses to acknowledge that Biff’s interests and talents are not suited for the sales industry. Overall, Willy loves Biff, yet he resents him for not becoming a successful salesman and believes he has failed out of spite.