One one side is special counsel Robert Mueller, who has subpoenaed Trump Organization documents as part of his wide-ranging investigation into the 2016 campaign. On another is Stormy Daniels, the adult-film actress seeking internal correspondence as part of her effort to be freed from a nondisclosure agreement centering on an alleged affair with Trump.
And in the most direct assault, the District of Columbia and Maryland have sued Trump, alleging that he is improperly accepting gifts, or "emoluments," from foreign or state governments through his businesses, including his hotels. A federal judge ruled Wednesday that the case can proceed, opening the way for the plaintiffs to seek at least a portion of Trump's tax returns, which the president has refused to release.
"I think under pretty much any reading of the judge's order, we can get discovery of his personal financial information in that it relates to payments from foreign and domestic governments," Maryland Attorney General Brian Frosh said. He and D.C. Attorney General Karl Racine also plan to seek other documents related to the president's D.C. hotel.
The inquiries are exposing the risks Trump took on when he made the decision to maintain ownership of the company that bears his name while serving in the White House - a departure from 40 years of presidential tradition and the advice of ethics officials.
Previous presidents have chosen to fully divest their assets. When Trump took office, he instead put his stake in his company into a trust managed by his sons, accessible to him at any time.
Now, what initially seemed like a plum arrangement for Trump - enjoying the fruits of his business while running the country - may come back to harm the Trump Organization if it is forced to reveal the kind of financial information and private correspondence that real estate firms closely guard.
During the campaign, Trump played on his reputation as a successful businessman, boasting of his real estate projects while refusing to disclose financial information that might have corroborated that image. He deflected calls to release his tax returns, a disclosure every president has made since the 1970s.
Since taking over the business, his grown sons, Donald Trump Jr. and Eric Trump, have at times remarked that one of the benefits of running a private company is the ability to avoid the scrutiny and pressure faced by publicly held firms.
"We're not a public company," Eric Trump told The Washington Post shortly after taking over, a fact he has reiterated since. "If we want to add 20 properties to our portfolio in one year we can do that; if we want to add zero to the portfolio in a given year, we can do that."
Company officials argue it would have been impractical to untangle and sell all of Trump's real estate holdings, and that doing so might have created additional conflicts of interest.
No private real estate developer wants its plans, financial information and partnerships thrust into open view, as they amount to proprietary information. But that is exactly what could be at stake for Trump.
Since last year, the company has received subpoenas as well as informal requests from investigators with Mueller's office seeking documents related to Trump's past business activities in Russia, according to several people familiar with document subpoenas and witness interviews.
The requests are broad, according to the sources, including information regarding the company's plans for a Trump-branded property in Moscow and communications with Felix Sater, Trump's partner on Trump SoHo in New York, which has since left the Trump chain.
Alan Futerfas, a New York attorney representing the Trump Organization, said that the subpoenas are "old news" and that the company's "assistance and cooperation with the various investigations remains the same today."
Whether Trump had an extramarital affair with Daniels a decade ago - something she alleges and he denies - her lawsuit is bringing scrutiny to the company as well.
Daniels received $130,000 from Trump's personal attorney, Michael Cohen, as part of an agreement to keep silent about her alleged relationship with Trump more than a decade ago. Cohen used his company email account in negotiations, and on Sunday's "60 Minutes" show, Daniels's lawyer, Michael Avenatti, said the agreement was mailed to Cohen at his Trump Organization address.
Avenatti argues that the Trump Organization has "unmistakable links" to the case. He has sought depositions of Trump and Cohen and made up to 10 requests for documents, though a judge deemed the requests premature.
Other current or former Trump Organization employees, including attorney Jill Martin and former Trump bodyguard Keith Schiller, could come under scrutiny for their alleged roles in facilitating meetings with Daniels or covering them up.
In a statement provided to The Post by Cohen, the company has said it "has had no involvement in the matter."
The attorneys general's suit is potentially the most consequential, with this week's ruling setting the stage for the plaintiffs to possibly seek private documents related to the Trump International Hotel in Washington - a property Trump once used as a backdrop for a campaign event featuring hundreds of hotel staff.
One possible outcome of the case, Racine said, is that Trump could be forced to "divest from any financial interest he has in the hotel."
Some law professors following the case said that significant impediments remain for the plaintiffs. But they have likely cleared their biggest hurdle toward requiring the company to produce records related to the hotel as part of the legal process known as discovery. Some of the records may be made available to the public, some may not.
"We will be able to get broad discovery in regards to the Trump hotel's business and the sources of that business," Racine said.
The Justice Department, which is defending Trump in the case, maintains that the case should be dismissed and has not said whether it will appeal the judge's decision.
The company issued a statement saying that "the court has yet to rule on several additional arguments, which we believe should result in a complete dismissal."
People who have sued the Trump Organization in the past said it has been unusually fierce in fighting document requests. "We got, in five years of litigation, what should have been done in less than a year," said Daniel King. An attorney, he represented clients from a planned Trump development in Mexico who sued after the project failed and their deposits were lost.
In 2006, Trump sued reporter Tim O'Brien for defamation after O'Brien reported that Trump's net worth was far less than the billions he had claimed. As part of the litigation, O'Brien sought internal Trump documents - including the businessman's tax returns - in an effort to establish Trump's actual assets and income.
"The first time that they gave us the tax returns back, it looked like a crossword puzzle, because so much had been redacted," O'Brien said. In one case, he said, "the only line item that was showing was [Trump's wife] Melania's modeling income, which we had no interest in knowing about."
The case was ultimately dismissed, and O'Brien did not get the information he sought.
"Trump's problem from the beginning has been a willingness to mix business with governance, and not to make a sharp distinction between the two," said George Brown, a law professor at Boston College. "Well, it's conceivable that this lawsuit, if it proceeds down a certain path, will force him to rethink that."
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The Post's Frances Stead Sellers, Tom Hamburger and Emma Brown contributed to this report.
(Except for the headline, this story has not been edited by NDTV staff and is published from a syndicated feed.)
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