Not surprisingly, he behaves like a dick:
Though Trump is pitching himself to voters as a dealmaker who wins, the 12-year drama of the Trump International Hotel & Tower offers a more complicated narrative. While it reinforces his preferred image as a bold risk-taker and consummate salesman, it underscores his darker reputation as a bullying businessman willing to back out of deals and trash the competition when it's convenient. And that big TRUMP sign on the front of the building fits perfectly with the caricature of the developer as a narcissist and braggart.
Altogether, buyers of 43 condos—32 residential units and 11 hotel units—took advantage of [a 10% discount "friends and family"] deal, a group that included attorneys at DLA Piper, Trump's law firm, and architects at Skidmore Owings & Merrill, which designed the skyscraper. Some buyers demanded that Trump honor his original deal, and Trump backed down. Others were unwilling to jeopardize a valuable business relationship and simply accepted Trump's new terms without a fight.
Trump took on another group—his financial backers. Unable to pay off a maturing construction loan from a bank group led by Deutsche Bank, he sued them in 2008 for more time, citing a “force majeure” clause in his loan agreement. Such clauses are designed to give borrowers relief in the case of unforeseen, cataclysmic events, like floods or wars, but Trump argued that the financial crisis qualified. He also sought $3 billion in damages.
That a good 25% of American voters support this guy turns my stomach. But evidence about how he behaves, and how he repeatedly tries to screw his counterparties on deals, actually boosts his standing among those voters. Regardless of the outcome of this election—I'm hoping for something like the Whig implosion of 1852—it speaks poorly of our country that he's got this much support.