Even the conservative Wall Street Journal has figured out that President Donald Trump isn't the master negotiator he's long branded himself as -- but Trump's former business associates say they've known Trump was bad at making deals for years.
Jack O’Donnell, a former Trump casino executive, tells Politico that Trump's typical negotiating style is to act, as the publication puts it, as a "for-show tough guy." However, when it comes to the details of negotiating, Trump leaves most of the heavy lifting up to others.
"He’s not the guy that’s sitting down face to face doing the negotiating—he just didn’t do that with the deals we were involved in," O'Donnell explains. "I mean, listen, we did have to go to him, but it was more, ‘What are we willing to pay for this?’ ‘Well, we’re willing to pay $12 million... or whatever the number was. And he’d go, ‘Yeah, get it at 12. That would be great.’ But literally that would be a 30-second conversation."
One problem with Trump's negotiating prowess is that, once he decides that he wants something, he will not hide his desire to overpay to acquire it. In particular, Politico points to Trump's statement during negotiations for Manhattan’s Plaza Hotel in which he said, "How can I live without it?"
Trump wound up paying $60 million more for the hotel than high-end estimates of the hotel's worth.
And Bruce Nobles, the former president of the Trump Shuttle, says that Trump got easily played by Frank Lorenzo, the man who sold him the Eastern Air Lines Shuttle in 1988.
“The price was too high,” he says. “Lorenzo said, ‘I really want to sell it,’ and Donald said, ‘I really want to buy it.’”
Once again, Trump wound up paying an estimated $60 million for the shuttle than high-end estimates said it was worth.