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WILLY: … was rich! That’s just the spirit I want to imbue them with! To walk into a jungle! I was right! I was right! I was right! (Act 1)
Willy interprets Ben's tangible wealth as proof of the worth of his family and himself. He wants his son to be like his brother – unafraid to go out and make their own success.
WILLY: I’ve always tried to think otherwise, I guess. I always felt that if a man was impressive, and well liked, that nothing—
CHARLEY: Why must everybody like you? Who liked J.P. Morgan? Was he impressive? In a Turkish bath he’d look like a butcher. But with his pockets on he was very well liked. (Act 2)
Charley is a pretty realistic guy. He tries to make Willy see that being well-liked isn't as important to success as Willy thinks it is. Of course, Willy refuses to see the truth of this.
WILLY: Without a penny to his name, three great Universities are begging for him, and from there the sky’s the limit, because it’s not what you do, Ben, it’s who you know and the smile on your face. It’s contacts, Ben, contacts! The whole wealth of Alaska passes over the lunch table at the Commodore hotel, and that’s the wonder, the wonder of this country, that a man can end with diamonds here on the basis of being liked! (Act 2)
Willy desperately asserts that being well liked is enough to get you concrete wealth – yet this is clearly untrue in the context of the play. Instead, the play seems to suggest that hard work and daring will get you rewards. Is this totally true, though? Willy does have a point. Even today a lot of people do make a lot of money in just the way he describes above.