Trump’s problems (among others) are that he is impulsive and immune to listening to good advice. He times markets all wrong, buys properties at elevated prices because “he always wanted them,” changes his direction on a whim. Losing billions in real estate development takes some real (non)talent. Losing money running casinos, too. I am sure there were very smart people who told him, “Don’t buy the Plaza. It’s a money pit.” “Atlantic City has too many casinos now. It doesn’t need two more.” “There’s not enough passengers for a shuttle between Manhattan and AC.” “Omaha Steaks already sells damned fine meat.” “No one is going to buy Trump-labeled water.” “The Russians will expect repayment — or else.”
And so on.