Biff as high school football hero embodies his father’s dreams of being popular; in Willy’s oft-repeated words, of being ‘well-liked.’ Willy’s enduring philosophy, despite all setbacks, is that if one is popular then success and wealth will automatically follow.
Biff is certainly a social success in high school, but falls down badly when it really matters, when he fails to pass his final exams. This sets him on the road to failure, but years later Willy still doesn’t seem capable of grasping this. When Linda muses that Biff seems ‘very lost’, Willy responds:
Biff Loman is lost. In the greatest country in the world a young man with such - personal attractiveness, gets lost. (Act I)
Willy appears baffled by this state of affairs. He overlooks the fact that being ‘personally attractive’ is not necessarily of itself sufficient to achieve lasting success in life.
Both Biff and his brother Happy, it seems, have relied simply on appearances to get them through life, rather than maintaining a focus on their goals and upholding a serious work ethic. The result is that they have failed to achieve a career, family, or any kind of proper place in society. Meanwhile Bernard, the quiet, studious neighbour whom they used to mock for his physical shortcomings, has become a successful lawyer, by virtue of his own hard work.