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Are you asking if you can be prosecuted, or if he can sue you for the $500?
Mainly could I be prosecuted for something even if I never paid my buddy? And this is all hypothetical since my buddy didn't kick anyone's ass. Rather if he was to do it in the future.
Did you ever tell him that you were just kidding?
First, he can't sue you. Even if he could prove that you really wanted him to beat the other guy up, it would be an illegal contract, and no judge would enforce it.
Second, title 18 Pennsylvania statutes, Section 902 defines criminal solicitation as what happens when a person asks or entices another to commit a crime with intent that the crime be completed. If there's evidence that you were (a) drinking and (b) kidding, it would be difficult to prove that.
Also, the statute says that if, after making the offer, you make it clear that you do NOT want the person to commit the crime, or tried to stop him, that would be a defense.
So, in other words, I should make sure he knows I was only kidding and don't want him to do it.
what is a typical punishment if found guilty of criminal solicitation?
If you were found guilty, it would be the same punishment as for assault. Let me look that up.
Simple assault is a second degree misdemeanor, which means that it's punishable by a fine of $500-$5,000, up to two years in jail, or both. But, for a first offense, you wouldn't spend two years in jail.
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