Should I keep my friend of 20 years or just say he is no good and he has changed his ways?

Cute, your friend doesn't sound like a very nice person. It sounds to me like you are seriously considering telling him to bugger off. You don't need us to tell you what to do. If he's really getting on your nerves, and he's getting you down all the time, tell him how you feel. The best way to get rid of him, if he's not a true friend, is to tell him that you won't lend him any more money. If he's a real friend, that won't matter, but this man does not sound like a nice person, and I think he will leave you to sulk.