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WILLY: [the last to leave, turning to Charley]: I don’t think that was funny, Charley. This is the greatest day of his life.
CHARLEY: Willy, when are you going to grow up?
WILLY: Yeah, heh? When this game is over, you’ll be laughing out of the other side of your face. They’ll be calling him another Red Grange. Twenty-five thousand a year. (Act 2)
Willy's hopefulness that the game will turn out well for Biff is based on the belief that Biff has already won the game, performed flawlessly, and is headed for a professional football career. This kind of baseless optimism eventually destroys Willy and seems to seriously damage his sons.
BIFF: He walked away. I saw him for one minute. I got so mad I could’ve torn the walls down! How the hell did I ever get the idea I was a salesman there? I even believed myself that I’d been a salesman for him! And then he gave me one look and—I realized what a ridiculous lie my whole life has been. We’ve been talking in a dream for fifteen years. I was a shipping clerk. (Act 2)
Biff points out that because of excessive dreaming and fantasizing about a better future, he had lost his grounding in reality. When he forces his father to face this reality, it leads to Willy's destruction.
HAPPY: Dad is never so happy as when he’s looking forward to something! (Act 2)
Happy's statement reflects a fundamental understanding of his father's need to dream as a means of escape. Is Willy's family in some ways responsible for furthering his delusions? Or are they only trying to make their father happy?