Mayor Giuliani tried to argue Mr Trump was smart otherwise his investors would have sued him. So the question which you raise is, why didn't they sue him for losing $1B in a year?
Gov Christie tried to argue losing money is a genius plan to not pay taxes for the next 15 years. Let's ask people in business if their financial plans include a scenario to lose money to make money.
It's the optics. He is supposed to be for the little guy and yet there is no financial empathy.