Politely tell him he has a week or less (not sure how many days is good for you) and he needs to be out. He's not poor and has the funds to stay at a hotel/motel. In that time, he can drop off his car at the shop and they can repair it. Loaning a car to an uninsured, unlicensed person is a sure way for you to get dragged into legal problems when something happens. This person is an adult. They were professional lawyer and does not how to deal with this type of situation? Why are you dealing with this guy? His sons should have been out there to help out in one way or another. Suspect he might be wanting you to take care of his stuff for him too. Be kind but firm, a true friend will understand it.