Trump's businesses have never been under more fire, and they're facing their 'greatest challenge' yet

• President Donald Trump's business is under intense scrutiny unlike any time prior in his presidency.
• The special counsel Robert Mueller subpoenaed the Trump Organization for documents.
• Adult film star Stormy Daniels is seeking documentation from the company related to the $130,000 payment she received from Trump lawyer Michael Cohen.
• Lastly, there is a potentially huge emoluments clause lawsuit that a federal judge said can go forward.

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Never before has President Donald Trump's business come under the kind of fire it has in recent weeks.

Simultaneously, the Trump Organization is faced with three pieces of high-stakes litigation:

• The special counsel Robert Mueller has subpoenaed the company for documents as a part of his investigation into Russian interference in the 2016 presidential election.
• Stormy Daniels, the adult film star whose legal name is Stephanie Clifford, is seeking all internal company documents that have any relation to the $130,000 payment top Trump attorney Michael Cohen sent prior to the 2016 election - so she would stay quiet about an affair she says she had with Trump.
• The attorneys general for Washington, DC, and Maryland filed a lawsuit that claims Trump took "emoluments," or gifts from state and foreign-government officials, in violation of the Constitution. That lawsuit cleared an initial hurdle that no similar prior lawsuit had passed, with a federal judge ruling that the case can move forward.

All three of those cases could open the door to closely guarded Trump Organization documents - perhaps even Trump's own tax returns - becoming public. At the same time, Trump's company is receiving renewed scrutiny for its dealings in India and an episode between the Trump Organization and a Panamanian hotel owner that recently turned into a lengthy standoff.

"The Mueller subpoena of the Trump Organization, and the potential discovery in the Stormy Daniels case and the Maryland and DC emoluments case, do present Trump and his family businesses with the greatest challenge to their efforts to hide their business affairs from public scrutiny during his presidency," Larry Noble, senior director and general counsel of the Campaign Legal Center, told Business Insider.

The stakes are 'much higher' for Trump

Noble said that interest in the president's business and potential conflicts of interest was highest early in his presidency because "the issue was new to many."

"But what we could find out was largely limited to what he was willing to say, which was little, and the press could determine," he said. "Now, Trump is facing demands for information in legal proceedings, which are not as easy to evade, and for which there are penalties for lying. The stakes for him are now much higher and the chances of us learning the truth about his business dealings are greater."

The Washington Post reported this weekend that the series of inquiries "are exposing the risks Trump took on when he made the decision to maintain ownership" of the Trump Organization.

Prior to taking office, Trump opted to pass his stake in the company on to his two sons and a senior executive at the business, rather than fully divest from the assets as past presidents had done and as ethicists implored him to do. The issue garnered much attention in the administration's early days, but soon fell by the wayside as the special counsel's investigation ramped up and as Trump moved to put his mark on the presidency and change the government's course.

As a result, Trump was able to - for the most part - handle his business entanglements on his terms without much blowback. That could now change, especially if the company is legally required to release sought-after documents.

"President Trump's insistence on holding onto his business interests invites scrutiny of his business dealings and partners," Jordan Libowitz, a spokesman for the watchdog group Citizens for Responsibility and Ethics in Washington, told Business Insider. "Scrutiny has continued to grow into the matter, but it was most likely inevitable."

Alex Wong/Getty Images

Robert Mueller.

What is under examination

The Post reported that Mueller's request is "broad" and that the special counsel is likely seeking information on the president's business dealings in Russia - particularly as they relate to the company's plans for a Trump Tower in Moscow. Those plans did not come to fruition and seemed to be ditched amid his presidential campaign.

Meanwhile, Clifford's attorney, Michael Avenatti, insists that the Trump Organization has "unmistakable links" to his client's lawsuit. He has asked the company to preserve all paperwork regarding Clifford. The company itself denies any involvement in the episode, although Cohen used his Trump Organization email as part of his involvement with the payment while another top Trump Organization official was on an email correspondence. The company said that official, attorney Jill Martin, was not representing the company.

The final bit of litigation, which could prove to be especially tricky for Trump and his business, accuses him of violating the emoluments clause of the Constitution by taking payments from state and foreign-government officials via his hotel in Washington, DC. US District Judge Peter J. Messitte ruled last week that the attorneys general have legal standing to sue the president, though his decision is likely to be appealed. If it stands, Maryland's attorney general, Brian Frosh, and DC's attorney general, Karl Racine, may be able to seek Trump Organization documents related to the hotel.

On Monday, New York magazine's liberal pundit Jonathan Chait argued that the conflicts of interest and appearance of "corruption" would be Trump's biggest liability that Democrats can capitalize on in the midterm elections - not the wide-ranging Russia probe.

"Trump represented himself as a rich man feared by the business elite," Chait wrote. "He had spent much of his life buying off politicians and exploiting the system, so he knew how the system worked and could exploit that knowledge on behalf of the people. In fact, his experiences with bribery opened his eyes to what further extortion might be possible. Trump was never looking to blow up the system. He was simply casing the joint."