Bankruptcy is not necessarily a indication of being a poor businessman.
You have to look at the whole of his financial history. What have been his highs?
Many of the most successful businessmen in history have made and lost fortunes several times.
The most successful businessmen have been risk takers. With great risk you occasionally have great failures.
Yeah, but who do you want to have to pay for other people's great failures? The taxpayers? A truly successful businessman would not need somebody to bail him out ... EVER!
Dave Ramsey filed for bankruptcy. Just saying.
It is also difficult to be successful if you play by the rules but there is a group of people who can subvert the entire economy through changes in monetary policy.