I get that, a lot of people hated that. The richer you are, though, the more likely you are to have this kind of thing happen. Remember he did not personally go bankrupt. Individual companies went bankrupt. He plays in very high risk / high reward markets. Real estate brokers like him go bankrupt if they have too much coffee in the morning - or not enough.
His first bankruptcy was in 1991, when the Taj Mahal Casino went under. I don't know how old you are, but that was the gulf war, severe recession, etc. The reason you split things into different companies in the first place is to handle risk. If you don't, the failure of the Taj potentially spreads to every company. Now instead of screwing a couple of banks and laying off let's say 1000 people, you are screwing over dozens of banks and multiple thousands of employees.
Remember that this kind of setup is in the interests of the banks too. I'm not going to invest in a promising hotel project if I could lose everything because a casino goes bankrupt.
Was his bankruptcy a selfish act of a predator? Only he can truly answer that. But to me that is all noise.
His policies made your life better, my life better, and the lives of millions of Americans better. Not only that, his policies improved the lives of millions around the world. I am so done with the BS I get from <pick your media outlet> and <pretty much every f***ing politician out there>. Ever since Bush Jr. bailed out those disgusting pricks on Wall St. for NO REASON (a rant for another time), I've been moving away from relying on party and looking at results. You also have to dig like a gopher to find the truth.
Way too long a post, but I'm always happy when somebody is willing to have an actual discussion.