Roommate Troubles (very long, but in digestible pieces!)

[MattSuspect]

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Here's something you can do to make sure he knows his place in life...if at 11:00 (or some other time closely approaching the 11:59 deadline) he has not packed and does not look ready to leave, call the cops, they're probably not gonna arrive until 30 minutes after wards anyway. It'll take you a full 10-20 minutes to explain your story, and by then it'll be almost 12:00. He'll be faced with the choice to either leave immediately & send for his stuff later or be arrested. In either case you would've put the bastard in his place - where he belongs. All of this will ensure you will:
1)get the last laugh
2)make him think twice before pulling some crap like this on you again
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Nice try, but there is no way that a police officer is going to get in the middle of a bunch of smartass college kids and decide to force out into the street, without a court order, someone who is clearly living there.

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OP is living in Manhattan, and is out of college.