What is the meaning of Willy pawning his diamond watch fob? Also what is the meaning of Biff's radio correspondance course that Willy paid for with the money he earned for selling the diamond watch fob?
In his autobiography, Arthur Miller wrote that the characters of Death of a Salesman speak in a stylized manner
...to lift the experience into emergency speech of an unabashedly open kind rather than to proceed by the crabbed dramatic hints and pretexts of the 'natural.'
Willy's having sold the diamond watch fob indicates his willingness to separate from the past and devalue his brother's affection in order to further his dreams for his son Biff. The "crabbed dramatic hints" here are that Willy's American Dream is a distorted one; for, it is a dream of money and success.
When he has learned of his father's philandering with "The Woman,"and abandoned taking summer school to make up the math credits, Biff faces an empty future. So, Willy sells his diamond watch fob for Biff to take a radio correspondence course in the hope that Biff can learn to be a successful speaker which will aid his success in business.
WILLY. Whatever happened to that diamond watch fob?...When Ben came from Africa...?
LINDA. You pawned it, dear...for Biff's radio correspondence course.
While Willy's imagined conversations with his brother Ben indicate his desire to connect with his family,he has pawned the meaningful relationships and values for the skewered American Dream of materialism.