At practically every stop in his wild and thus far successful ride to the Republican nomination,
But if he actually reaches the White House, the sheer size of Trump's holdings, his active role in varied companies and his knack for self-promotion will pose unprecedented political, financial and ethical challenges.
If elected, Trump would almost certainly be the richest person ever to occupy the White House. Independent estimates of his wealth range from a few hundred million dollars to $4.5 billion by Forbes magazine. He claims to be worth $10 billion, but has thus far refused to release tax records.
According to Trump's personal financial disclosure, he is an executive, trustee or member of about 480 corporations, partnerships, limited liability companies or foreign entities. Throughout the campaign trail, he has been unabashed in plugging many of his businesses and the Trump brand – for which he receives licensing fees on clothing and other goods. Trump has crowed about his country clubs, hotels, casinos, ice rink, as well as his companies selling steaks, magazines, water and wine.
"It's really wonderful to have you at Trump National Golf Club.… It's a Jack Nicklaus signature course, a great, great resort and place," he told a throng assembled Tuesday in Jupiter, Fla., site of one of his dozen golf clubs, during a news conference after his primary wins in Michigan and Mississippi.
"I have very successful companies. I built a great, great company. I have very low debt. I have assets like this," Trump bellowed as he stretched out his arms wide before reciting a litany of his businesses.
If elected, nothing under current federal law would force Trump to sell his companies or stay out of their business decisions, though by tradition presidents have put their investments in blind trusts. There are well-established conflict-of-interest rules for other executive-branch officials, and less-strict ones for members of Congress. But whether such laws would apply to the nation's chief executive is less clear.
In a 2014 report on conflicts of interest in the executive branch, the nonpartisan Congressional Research Service noted that the criminal statute requiring officials to recuse themselves from government matters in which they have a financial interest "expressly excludes the president and vice president."
So while Trump still would have to avoid taking any official action specifically intended to benefit his financial interests, as federal law broadly prohibits, when it comes to dealing with his complex holdings, he would be largely left to chart his own course.
The 69-year-old has said repeatedly that he would have his children manage his enterprises if he became president, though experts doubt that would be enough distance to remove suspicion. The Office of Government Ethics, which oversees conduct for the executive branch, specifically states that a blind trustee cannot be a relative, and more generally warns about government officials' actions that could benefit the financial interests of family members.
The idea of a blind trustee is to have stocks and other assets managed, bought and sold by an independent third party, without the knowledge of owner. It is intended to remove the appearance and possibility of self-dealing. And from at least the days of
But for Trump, whose assets include many fixed properties bearing Trump's name and stakes in Trump-labeled ventures, a blind trust may not work.
"He cannot put businesses he owns in a blind trust and suddenly get a case of amnesia," said Skadden Arps attorney Kenneth Gross, who has helped billionaire Michael Bloomberg and other officials set up blind trusts. "We're in uncharted waters at the presidential level."
The potential conflict would come, he said, if a future Trump administration, for example, declared a parcel next to a Trump golf course as public land, causing the value of his golf property to triple; or if a President Trump had dealings with a leader of a foreign country where businessman Trump operates a casino. Even the new Trump International Hotel that he is building on Pennsylvania Avenue, about a half mile away from the White House, makes some people a little uncomfortable.
"Any time he does anything related to the economy, if he cuts corporate taxes, people are going to say, 'Wait a minute, you're doing that to feather your own nest,'" said Michael Genovese, an American presidency scholar at Loyola Marymount University in Los Angeles.
Genovese said Trump would be better off giving his business interests to an independent party, for political reasons, if not for appearances alone. "In the long haul, it would be a liability," he said. "Every decision he makes that has any kind of economic impact, his critics – and there will be many – are going to pound it and pound it and pound it, and create suspicion."
In times past, large personal fortunes seemed hardly to matter for presidential politics. George Washington, a major owner of plantations and slaves, was one of the richest-ever presidents in inflation-adjusted dollars, while Abraham Lincoln was famously one of the poorest. Both routinely rank as the most acclaimed presidents in U.S. history. And Trump is in good stead with most American presidents, who have typically been men of means, from plantation owner Thomas Jefferson to international businessman Herbert Hoover to trust-fund baby John F. Kennedy.
In the modern era as well, wealth has provided the leisure and means for individuals to get to the White House. For all the public outcry over income inequality and the top 1%, Trump's super wealth seems to have only endeared him to his most ardent supporters -- less-educated working-class men.
Trump's money is certainly helpful in financing his campaign too. Whether it's getting around in his own Sikorsky choppers or staying in the penthouse of Trump Tower, his wealth gives him some real advantages over less-well-to-do rivals such as Sen.
But Tom Cronin, a political science professor at Colorado College, wonders whether Trump too could soon come under tougher scrutiny for how he made his money and past bankruptcies of some of his ventures. Already his critics, including Romney, the wealthy candidate whose own image was battered by accusations of greed, have accused Trump of running slipshod businesses, including the now-defunct online education operation known as Trump University, the target of a class-action fraud lawsuit by former students.
Certainly some of the most popular presidents were wealthy themselves, reflecting in part the notion that a person so rich can't be bought. But experts say there's little evidence that business skills translate into the public sector. "If anything, the research would point the other way," said Andrew Rudalevige, a professor of government at Bowdoin College in Brunswick, Maine.
He noted, for example, that Trump had boasted he could build a wall along the U.S.-Mexican border for $8 billion, far cheaper than what it would cost government to do the same job. But that shows you precisely the difference between the private and public sectors, Rudalevige said.
"In the public sector, there's a lot of restraint. There's competitive bidding, restraints on whom you can hire, transparency and other requirements to deal with corruption," he said. "Pound for pound, that makes it less efficient than the private sector. But the government is not about being fast and cheap, it's more about being representative, transparent and doing things in nondiscriminatory ways."
And for all of Trump's business negotiating skills, the question is whether the kind of deal-making that he has done is anything like the job of a president.
"The whole notion of business hierarchy is so different than government, which is incredibly fragmented in power," said Genovese of Loyola Marymount. "Trump has a lot of latitude to hire and fire [at his businesses]. He won't be able to fire members of Congress."