1991, 1992, 2004, and 2009. Doesn't seem to be improving much.And yet he is ubrer-wealthy.
Failure is a great teacher....provided one eventually graduates from it.
He even said himself that bankruptcy is a useful tool that he uses. Those four instances were all corporate bankruptcy, not personal bankruptcy, although one of them did come close to personal bankruptcy. The people that end up getting screwed in those bankruptcies are probably people other than himself, like creditors and possibly the employees. Not a great background for being president, when presidents can screw up the federal budget and then just walk away without personal financial damage from it.