I have a similar question-in the state of SC I had a guy wanting to sublease my apartment with a verbal agreement for 700 a month for 2.5 months. He left after three weeks of living in my room with no check. I have 2 roommates that are willing to say we had an agreement, and I have personal items of his that proved that he had lived in my apartment. He has gotten in trouble with the law before but comes from a wealthy family and has a good lawyer. Do I stand a chance in small claims?

Small claims will not cost you so you can try. A judge will not think much of your landlord skill if you went with a verbal , no security and no up front payment. I'd probably walk away

Do you have a lease? Does this lease allow you to sub-let the premises, or to have non-related persons living with you?

Many small claims courts do not allow attorneys so having good lawyers may not help.

If you can prove you had an agreement and that he lived there, you should win, but collecting will be another issue.