Donald Trump’s critics say the only way for him to keep his business interests separate from the public’s interest is to simply get out of business entirely, selling his companies and putting the proceeds into anonymous assets that someone else can manage.

But there’s nothing simple about it: unloading a real estate empire as large as Trump’s is a lengthy, complicated process fraught with ethical pitfalls, one that could end up costing a fortune.


“He has to make a choice,” said David Reiss, director of Brooklyn Law’s Center for Urban Business Entrepreneurship. “How much pain is he willing to take?”

Trump, who’s expected to lay out a plan to address conflicts of interest at a press conference Wednesday, heads a particularly difficult estate to unwind. Forbes has pegged his net worth at $3.7 billion in September, attributing most of that to real property holdings tangled in debt, partnership agreements, management contracts, branding deals and tax deferrals.

Ethics watchdogs say Trump’s cleanest break would be to sell his company to the public, but an initial public offering — especially one that folds in most or all of Trump’s scattered businesses — would be complicated, costly and time-consuming.

“The nature of the business doesn’t lend itself to going public,” said Jan Baran, co-chair of Wiley Rein’s election law and government ethics practice. “Rolling in all the real estate and the royalty contracts and all the other orphans like wineries and steaks, it’s a little hard to imagine any public companies that resemble what his business is, because it’s such a hodgepodge of things. It would take a while, it would take at least a year.”

What’s more, Baran noted, an IPO would require underwriters to raise capital and pull together an offering — raising new concerns about investment firms potentially currying favor with the new administration.

“Are the ethics complainers willing to let Goldman Sachs do the underwriting on this public offering?” he said. “Somebody’s got to put it together.”

Even if Trump chose to skip the IPO and just liquidate his assets via direct sales, he’d face a complex task — and a costly one.

“This would be an extraordinarily difficult situation,” said Neil Shapiro , a law partner at Herrick Feinstein in New York. “It would certainly be unprecedented in terms of somebody liquidating a portfolio of this size. We’re in uncharted territories here.”

The problems start with finding a buyer. The pool of people shopping for, say, a Fifth Avenue skyscraper is small, and only the buyer and seller can say for sure whether the price paid is fair. As such, selling a property raises nearly as many ethical quandaries for Trump as owning it. A buyer looking to curry favor with the next president might pay too much. Another might do Trump a favor by making a quick deal while paying too little.

Compare Trump’s holdings to those of his pick to lead the State Department, ExxonMobil CEO Rex Tillerson, who has a far more clear path toward untangling himself from his estate. Tillerson’s fortune is tied up in shares of stock, assets that can be sold to thousands of anonymous buyers at a price set by the stock exchange.

“You can sell stock anonymously at a price that will be the market price,” Baran said. “When you own a piece of real estate, you don’t sell that anonymously — you’ve got to find a buyer, and then you have to negotiate a price.”

Rising interest rates and a shifting real estate market would add to Trump’s financial woes if he were to sell everything. Of 28 Trump assets Forbes examined last year, 18 had lost value, including Trump Tower on Fifth Avenue in Manhattan.

Then comes the cost of the legal unwinding. Commercial projects typically have multiple partners with contracts designed to bind them together, and Trump’s are no exception. In San Francisco, Trump owns only 30 percent of the 555 California St. tower. And the building housing the Trump International Hotel in downtown Washington, D.C., is owned by U.S. taxpayers — as the General Services Administration leases it to Trump.

Unwinding such partnerships is costly by design, especially for a minority owner like Trump. Contracts might limit who a partner can sell his or her interests to, for example, or prohibit smaller shareholders from selling at all without a majority partner’s say.

Even when the divorce is cordial, Trump’s partners have a duty to their own stakeholders to get the best deal they can, and that means squeezing all the cash they can from the president-elect.

“Now I have a building worth a dollar and I’m selling it to my buddy for 70 cents. That’s no fun,” said Burl East, chief executive officer of American Assets Capital Advisors, a San Diego-based investment firm. “Take this little story and multiply it by 30 or 40 times. You have a quagmire of complex negotiations that probably would take a couple years.”

In some cases — such as with the Trump Parc Stamford condo project and a planned Trump Tower in Mumbai — all Trump owns of a building is his name above the door. In contract legalese, he’s a “key man,” the individual who delivers value to the property.

Getting out of a trademark deal could be tough, because the minute his name disappears, the building is worth less. Building owners and property managers would have to be compensated for that loss of value.

Even without Trump the name, Trump the person brings cache — and value — to properties such as Mar-a-Lago, which stand to lose value when Trump leaves. That’s when the lawsuits start.

“People aren’t paying for waterfront views. They’re paying for the fact that Christmas at Mar-a-Lago brings Donald Trump,” said David Bach, senior associate dean at the Yale School of Management. “They might feel their membership is worth less if the club is owned by someone else.”

Finally, the tax man would add to Trump’s misery. Real estate investors commonly defer capital gains taxes by flipping the profit from a building’s sale into another building, in what the IRS calls a 1031 exchange. As long as the profit is locked up in another property, no taxes are due. But once an investor cashes out, the tax bill can be enormous.

“It’d be hard to disentangle himself from this. It would take time. It would take lots of lawyers,” Bach said. At the end of the day, "there wouldn’t be a Trump empire anymore.”

Ethics laws allow for a tax-free trade of assets for people selling off holdings in order to comply with conflict-of-interest rules upon entering government. As long as the money goes into a diversified fund or Treasury bonds, the official can defer capital gains tax on the sale of their original holdings. Because the president and vice president are exempt from the ethics law requiring divestiture of other officials, though, it’s not a given that Trump would qualify for the tax break.

The part of the code providing the break, Section 1043, does not explicitly exclude the president and vice president, though tax lawyers said Trump would probably be able to get a certificate of divestiture allowing him to defer gains tax.

Simply turning his business over to his children, meanwhile, would trigger the gift tax.

“There is a little legal uncertainty, but if he’s going to get out for ethical reasons, he shouldn’t be penalized. He should be able to take advantage of what the statute provides for everybody else,” said C. Boyden Gray, White House counsel under George H.W. Bush.

If Trump does choose to sell it all, he’ll likely appoint a trustee to do the work and avoid sticky situations, lawyers said.

“Sign all ownership and management interests over to a trustee, and let him or her worry about it,” said Norm Eisen, President Obama’s former ethics czar. “It’s harder for the trustee, but I and most others would be patient while he worked it out, and that would be his only job.”

That gets to the real reason ethicists don’t expect Trump to divest: it would be hard for him personally.

“The self-made people, they put their heart and soul into creating it, and they’re not going to be cavalier about parting with it, nor should they be,” said Meredith McGehee, policy chief at Issue One and strategic adviser at the Campaign Legal Center.

“But it was his choice to run for president,” she said. “If you don’t want to go through the hassle, then don’t choose to run for high office.”