His business career vaulted him to fame, and he had notable successes, perhaps most prominently the rehabilitation of the Commodore Hotel and the construction of Trump Tower. But he often reached further than he was able to deliver. His record in business was pockmarked with plenty of failures.
The Trump Shuttle airline? Failure. His dreams of building a Television City in Manhattan? Failure. A United States Football League franchise? Failure. The Trump Plaza Hotel and Casino, Trump Taj Mahal, Trump's Castle Casino Resort, Trump Mortgage, Trump Vodka, Trump University, Trump Steaks, GoTrump.com? All failures.
His most spectacular flameouts came in the gambling mecca of Atlantic City, where he overextended himself building or buying three casinos that ultimately cannibalized each other's clientele as he failed to keep up with enormous debt payments. He filed bankruptcy for the Taj Mahal in 1991 and then for the other two casinos in 1992. He also filed bankruptcy in 1992 for the Plaza Hotel.
Even after recovering from that debacle, Mr. Trump failed again. His casino company filed for bankruptcy in 2004 and then again in 2009, for his sixth trip into that process. In his various bankruptcies, he was compelled to sell assets, and creditors were forced to write off some of his debt. But Mr. Trump has boasted that he still made money in Atlantic City even after leaving a trail of losses for nearly everyone else involved, including workers who lost jobs.
Mr. Trump played the game along the edge, and sometimes over the line, of propriety. To grease his path, he would hire a governor's son or a federal prosecutor's brother. Along the way, he was investigated time and time again. Federal, state and local authorities looked into his ties with the Mafia, found violations of money laundering laws and penalized him for skirting stock trade rules.
At one point when Mr. Trump was strapped for cash to make an interest payment, his father sent a lawyer to one of the son's casinos to buy $3.5 million in chips without placing a bet. New Jersey's casino regulators imposed a $65,000 fine for what amounted to an illegal loan.
But Mr. Trump makes a point of not admitting misdeeds or mistakes. Even his failures he portrays as triumphs. "I made a lot of money in Atlantic City," he once said, "and I'm very proud of it."