Let me surmise what are the things you can learn from multiple bankruptcies.
1st bankruptcy - You will learn and know who your real friends are because many of your "friends" will avoid you during your bankruptcy for fear that you will borrow money from them. You can tell who your friends and foes are by now.
2nd bankruptcy - You will learn and understand more about yourself because you know what you can and cannot do in life by now. In short, you know your own capabilities after your 2nd bankruptcy.
3rd bankruptcy - You will learn and understand this world better than other people after having gone through the vicissitudes of life. You will know how this world works by now. This was also the reason Trump got elected to be the US president because he understood how the US system was like after his numerous bankruptcies.
Trump knew who would make him lose his presidential and had fired a few hawkish people in his team.
The hawkish people are:
James Mattis
Steven Bannon
John Bolton
The remaining hawkish people in his team are feeling apprehensive now because they are fearful of their dismissals if they continue to be aggressive.
Let's see how this will affect future US political policies.