The Wall Street Journal published a report on Thursday claiming Trump has made millions of dollars endorsing a multilevel marketing firm called ACN. The company has undergone regulatory investigations regarding pyramid scheme allegations in three countries -- allegations Trump told WSJ he had never heard of.
"I do not know the company. I know nothing about the company other than the people who run the company," he said.
He has also gotten into hot water recently over Trump University -- now known as the Trump Entrepreneur Initiative -- and the implications of its name. The seminar initiative has him embroiled in two lawsuits in New York and California for misleading people into believing it was an actual university.
The real-estate magnate turned presidential candidate hasn't always shown the best judgment. His list of film credits, for example, includes awkward appearances in The Little Rascals, Home Alone 2 and Zoolander.
At other times, however, he appears incredibly shrewd.
Case in point: his purchase of thousands of Web domains, many of which include his name and/or negative remarks about his businesses, as a way to keep others from getting to them.
"It's very difficult to predict what the man will do tomorrow, and whether or not any of it is rational is very difficult to analyze and assess," said Wayne Barrett in an interview with TheStreet. Barrett began covering Trump in the 1970s and published the book Trump: The Deals and the Downfall in 1992. Over the years, he has examined a number of Trump's business maneuvers and uncovered various rather unsavory details, ranging from broken promises to suspect business deals and even ties to the mob.
Even the reasoning behind his presidential bid, for Barrett, is a black box.
In a 2011 piece for The Daily Beast, he suggested that pending lawsuits and shady partners were what ultimately kept Trump from making a presidential bid in 2012. Today, however, Trump appears to have no such qualms.
"Why didn't he run in 2012, and why is he running now, and why does he say the crazy things he says? It's very, very difficult to analyze, because he's all over the map, he doesn't respond to ordinary political analysis," Barrett said. "A certain percentage of the Republican electorate doesn't care."
There is no denying Trump has had incredible accomplishments in his career, the latest being his rise to the top of the Republican presidential pool, despite multiple gaffes, each one big enough to fell much stronger candidates.
"Trump's problem is not so much what he's done, but how he's done it," Barrett wrote in a two-part story on the now-billionaire that appeared in The Village Voice in 1979.
The assessment still rings true today. Here are four times when Trump was at his worst -- or best -- depending on how you look at it.
1. The First Deals
Trump's first major deals were facilitated by high-profile connections and unprecedented subsidies and tax breaks from the government.
His father, Fred, was a builder and real estate developer who specialized in housing projects in the New York City boroughs of Queens, Brooklyn and Staten Island. His experience and political ties -- largely through Brooklyn's Madison Club -- helped Trump to hit the ground running when he moved to Manhattan in 1971.
When the Pennsylvania Central Railroad entered bankruptcy, Trump obtained an option on its yards on Manhattan's west side and on the Commodore Hotel near Grand Central Station. He eventually transformed the yards into a convention center site and housing development, but he made arguably the biggest splash with the Grand Hyatt Hotel.
Trump obtained the hotel option in 1974 and signed a partnership agreement with the Hyatt Hotel Corporation the following year.
Wired into the administration of then-Mayor Abe Beame through his father, he then obtained unprecedented tax breaks and subsidies on the development, including a 40-year property tax abatement for rebuilding the hotel.
"The concept of giving enormous tax breaks to an economic development project selected by the government was unprecedented or at least unusual, and certainly it had not occurred in the City of New York. So the Beame administration, which the Trump family was directly tied into, they concocted a program to give to Donald," Barrett said.
The Grand Hyatt was nearly an afterthought for Trump -- Barrett pointed out that the option he originally turned in was unsigned, though no one noticed. But his dealings with it set the tone for what was to come.
"Both Fred and Donald Trump were state capitalists, they were essentially capitalists whose wealth was created by discretionary state decisions. And certainly, the baptismal project to Donald's life, the Grand Hyatt, was the beneficiary of not just city special subsidies and tax breaks but the state urban development corporation," Barrett said. "They were playing the angles, beginning with great connections to both the governor and the mayor, and they parlayed it into a great deal with city and state, without which they would never been able to do the Grand Hyatt project."