Should I reconnect with estranged friend?

If you truly want to rekindle your friendship, then you will HAVE to work it out. You will need to swallow your pride and talk WITH him and not TO him...then if you still want to be friends, you let the past be the past and move forward. If none of this sounds comfortable to you, then I don't think that it would be a good idea to rekindle...for either of you. At least not right now.