Penniless and naive, he can not pay for the journey and ends up getting mugged and having his boots taken from his feet by a gang of roving predators.
But since he always ends up losing the money, either by getting mugged or by getting drunk, it's obvious he won't be getting home any time soon.
He gets mugged for not putting up a fight against two men.
As he walks to class, he gets mugged by some students, as one of his friends watches.
He gets mugged by a man at the station who offers to help him with his luggage but instead steals all his money.