Why on earth would you throw away perfectly good money by bailing him out - especially after warning him of the consequences? Sometimes hard headed people don't learn until they GET a consequence. If you want to discourage him, tell him if he follows this course of action, you WON'T be bailing him out.
As far as actual charges, it depends on exactly how he gets in, who catches him, even what's in his pockets could make a difference. Could be anything from simple burglary (since it is an authorized entry to a structure) which carries a $2k fine and/or up to 12 years in prison (see RS 24:62) to defrauding a merchant, all the way up to a violation of one of the many Homeland Security statutes, in which case I wouldn't like to guess the outcome. (Better just hope he doesn't get caught sneaking into a section where some VIP like a Senator is sitting).
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While pointers can be helpful, ultimately the number one lesson in any legal action is: don't take legal advice from books, family, friends, co-workers, police officers, grocery clerks, web sites, or people on legal message boards. The only person who can give YOU legal advice is YOUR attorney.
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