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Jonesy gives a punishment to a student, Mr. Defuniak who is from Pittsfield:
Jonesy: You missed the test. And since you were ill, why not write me an essay instead? 3000 words on the short-term results of the Norman Conquest.
Mr. Defuniak: Yes, sir.
Jonesy: Better to be from Pittsfield than go back to it.
I didn't understand what actually he meant.
The correct quote, according to IMDB, is "Pittsfield's a better place to be from, than go back to."
Long story short, it's a small town. A good place to raise children (safe), but not a place where you'll make your fortune due to most of the work being blue collar. Furthermore, given the context, he's also implying that, without a proper education, Mr. Defuniak will never have the means or opportunity to succeed outside of town.
