Not that I like him at all, but the misunderstanding of his bankruptcies have become comical. Donald Trump, personally, has never, ever, ever filed bankruptcy. Donald Trump's businesses, which number well over 100, have filed bankruptcy exactly 4 times. Most of this is related to Atlantic City. Every major hotel operator in Atlantic City has declared bankruptcy.
As for Trump inheriting money, it has been stated that he received somewhere between 40 million and 200 million in 1974. He stated his worth in 1982 at 200 million. If he had invested in the S/P 500 from 1982 until now, he would be worth 8.3 billion. He is stating his worth is in excess of 10 billion, another estimate I saw was 8.7 billion. Either way, he has exceeded the S/P 500 over a 30+ time period, and having a 100% stock portfolio, as the S/P 500 is, is anything but conservative. I would also tell you that the period of time from 1982 until 2000 was the best 18 year run the market (hence S/P 500) has ever seen.
There is a lot of things to pick on Trump about, his ability to make money, employ 1000's of people thru good times and bad, pay millions of dollars in taxes, etc, is probably one you should stay away from.