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In movie The Departed, there's a line: "You will be on probation, see a court-ordered shrink......the whole nine yards."

What is shrinking by court order here?

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In "a court ordered shrink", a indicates that what follows is a noun. If you look up shrink in a good dictionary, you will find that, as a noun, it means a psychiatrist. court-ordered explains that the court will order you to see a psychiatrist.

the whole nine yards is an idiom meaning the whole of something, including everything related to it.

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