Do you really think the Native Americans made out better when they sold Manhattan Island?
Most definitely yes.
The Native Americans recieved roughly $24 US worth of 'trinkets' in trade.
Manhattan Island and New York City are so far in debt at present, that paying $24 US in 'trinkets' would require having to borrow $30 US to hopefully get enough money to pay for the $24 US in trinkets.
So what would you rather have? $24 US in trinkets or constant money headaches from massive debt? Good choice.