Death of a Salesman

First, we have to remember that Willy didn't even know what happened to the watch. Second, we learn that he pawned it to pay for a correspondence course for Biff. This tells us that Willy holds no emotional value in regard to family heirlooms, in addition to a lalck of money sense.  

WILLY: Whatever happened to that diamond watch fob? Remember? When Ben came from Africa that time? Didn’t he give me a watch fob with a diamond in it?

LINDA: You pawned it, dear. Twelve, thirteen years ago. For Biffs radio correspondence course.

WILLY: Gee, that was a beautiful thing. I’ll take a walk.