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catcher in the rye
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In the end of Chapter 2 of J.D. Salinger's The Catcher in the Rye, why does Holden think "Good luck" is a terrible thing to say?

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At the end of Chapter Two of J.D. Salinger's The Catcher in the Rye, Holden Caufield is leaving the home of his favorite former teacher, Mr. Spencer, when he is certain he hears the ailing old man shout toward him, "Good luck." While most would accept such a platitudinous send-off in the spirit in which it was given, Holden, the alienated, aimless teenager, resents the implication, declaring, "I'd never yell 'Good Luck!' at anybody. It sound terrible when you think about it."

Holden Caufield is the quintessential model of alienated youth, emotionally distant and intellectually stultified. He has little good to say about most of those with whom he has crossed paths, and has become the personification of ironic detachment. For an individual so jaded, a platitude like "good luck" carries little or no positive connotation. In fact, to Holden, when hearing it directed at him the phrase is insulting, because it implies that the recipient of "good luck" is borderline pathetic. This is why, later, at the end of Chapter Twenty-Five, the phrase again fills Holden with dread. Having paid a visit to his sister Phoebe's school, he leaves only to hear the elderly assistant to the principal of the school deliver that same bromide:

She yelled 'Good Luck!" at me the same way old Spencer did when I left Pencey. God, how I hate it when somebody yells 'Good Luck!' at me when I'm leaving somewhere. It's depressing.

Holden hates the phrase because it suggests that he needs a reversal of fortune, an ironic sentiment given that he does, indeed, require a different path than the one he is on.

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