It's simply not true that Trump hasn't suffered financially due to his Bankruptcies:
He funded the construction of the $1 billion Trump Taj Mahal casino in Atlantic City, N.J., which opened in 1990, primarily with junk bonds at a whopping 14 percent interest. A year later, the casino was nearly $3 billion in debt, while Trump had racked up nearly $900 million in personal liabilities
In March 1992, the Castle filed a prepackaged bankruptcy plan, and Trump gave up his 50 percent share in the casino for lower interest rates on $338 million worth of bonds.
In December 1992, Trump relinquished a 49 percent stake in the Plaza to a total of six lenders, according to ABC News. Trump remained the hotel’s CEO, but it was merely a gesture; he didn’t earn a salary and had no say in the hotel’s day-to-day operations, according to the New York Times.
more here:
http://www.politifact.com/truth-o-meter/statements/2016/jun/21/hillary-clinton/yep-donald-trumps-companies-have-declared-bankrupt/