Based on the facts that you stated, no one will get jail time.
As to court date, if they are to be brought to a different court and arraigned as adult, they will likely get different date. If this is the first offense, court tends to be more lenient than repeat offenders.
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Your parents should hire a criminal defense attorney in your area to assist you with your court date. The fines and jail time vary for a misdemeanor from state to state. If this is your first offense, you will not likly be looking at any jail time but community service or counseling could be a option.
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I'm not sure how you got a $500 fine if you haven't been to court yet. Also, if $50 is all the property taken is worth, then the offense is a misdemeanor. You can get jail time for this because the statute allows for it. In all likelihood, however, you will pay restitution and get some probation, but all depends on the facts.
The fine that you are referring to is most likely a civil demand letter that an attorney for the store will send to you. The law allows for a store in these types of cases to file a civil lawsuit to recover up to $500 above actual damages. If the store wants the money from the civil demand letter they have to file a civil lawsuit and they rarely do file suit. If they charged your friend with just a 1st offense shoplifting then he can not get jail time, however if they charge him with larceny under $250 then he can. I have provided a link below for more information on shoplifting offenses in MA.
This is not intended as legal advice and does not create an attorney-client relationship.
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