To me it sounds like a gamble not worth taking. How many transit tickets can someone have? Can't cost that much.
Is this person perhaps taking transit because he lost his license for a DUI? Are the unpaid fines related to that too?
Because that is a whole other can of worms. If I am not mistaken, DUI fall under criminal code now and can bar entrance to the US. I do know US citizens with DUI's get declined entrance to Canada, unless they do some reform program form or something, after 5 years have elapsed from the offence.
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