Kennedy and Obama were young presidents. I think they both did pretty good jobs, all things considered.
I certainly may be wrong, but I thought Trumps first casino was doing well in Atlantic City. So well that he decided to build another. And the competition against each other shut both down.
Not enough gamblers to support two casinos. Considering the overhead, 2000 people a night won’t work, but 4000 will.
Trump competed against himself. And lost.
Trump actually ‘owned’ three casinos (Trump’s Castle/Trump Marina, Trump World’s Fair, Trump Taj Mahal), although ownership is a bit of a questionable thing since he ended up giving significant interest over to Carl Icahn and other investors when he couldn’t finance or make a profit. Trump Marina is now the (new) Golden Nugget, Taj Mahal is now owned and renamed by Hard Rock, and the World’s Fair was famously demolished a couple of years ago after years of neglect and incomplete construction. Overestimating a saturated market would seem to be a key identifier of a poor businessman, although to be fair is is a mistake made by numerous would-be casino magnates as Atlantic City has come to be known as the graveyard of stillborn casinos including two more proposed by Trump prior to bankruptcy.
Failing to accurately survey the market and account for saturation is a key indicator of a terrible businessman, not limited to the casino business. Trump Airlines and the USFL are two notable examples of not really understanding the business or market before investing enormous sums of money into expensive and risky endeavors. Trump has it all figured out now, though, and has convinced other people to put themselves at risk for him and even pay him for the ‘privilege’ of using his name. “There’s a sucker born every minute…and two to take him.”
Trump isn’t a businessman. He is a greenmailer and litigant.