This sounds like LW doesn't know his friend. Plain and simple, people put up fronts. LW might be depending a little too much on "reputation", which he shouldn't have. If $1000 is enough to write a letter to Cary over, then maybe LW shouldn't have been doing business in the first place. You don't gamble with money that you aren't willing to lose.

As for the friendship, it no longer exists. If they'd had true friendship, the guy wouldn't have let LW high and drive over $1000.

Let him and it go. Lesson learned. Unless you want to sue, don't invite the vampire in to further disrupt your life.

Ah LW, i feel for you. I remember Gwool posting a memorable account of a friendship gone bad just out of the blue. I felt better after reading that because i've been in his position before. I've had friends like the one Gwool mentioned and like your "entreprenuial" friend. I believe his calling you may have something to do with maturity somehow descending upon him. He may have realized he reacted stupidly in the past and that cost him certain friendships. I don't know what to make of people like this other than to tell you to take them with a grain of salt. Concentrate on your friendships with people who you can really count on and who accept you for who you are. It's too much effort to go out of your way to avoid him so the best thing to do if he ever contacts you is to speak to him briefly and cordially and not give it a second thought. It's great that you got your cheque. Best of luck!