Wilbur Ross celebrated his greatest professional achievement on Nov. 30, 2016, surrounded by other executives in a noble New York restaurant between Broadway and Park Avenue. The shipping company Navigator Holdings had invited him to the timbered rooms of the Gramercy Tavern, where a private dining chamber awaited him.

At 79, there is little Ross hasn’t achieved as a businessman. He’s a multibillionaire who made his fortune restructuring and reselling ailing companies. He’s a member of New York’s most elite and affluent circles. And on that late November evening in 2016, he would also chalk up his next success. Then president-elect Donald Trump had tapped his old acquaintance to be the next United States secretary of commerce.

Politically, this is significant for several reasons. First, Ross is involved in deals concerning maritime freight, an industry – at least insofar as the U.S. is concerned – he is responsible for regulating as commerce secretary. Second, he is tasked with administering the “America First” trade policies Trump promised to his voters – yet at the same time, he profits from Russian competition on the energy market. And third, Navigator’s business partner Sibur is controlled by multiple oligarchs close to Putin who have Western sanctions in place against themselves or their companies. The connection is also problematic considering that hardly any other issue has dogged Trump’s presidency as much as his alleged contacts to the Russian government, particularly in the run-up to the election. A special counsel is currently investigating whether Moscow illegally supported Trump during his campaign. The first charges have already been filed and the first arrests made, including that of Trump’s former campaign manager, Paul Manafort.

They called him King of Bankruptcy

With such a large number of potential conflicts of interest, the U.S. Congress and the American public might have appreciated being informed that the designated commerce secretary played a role in the Russian gas business. No one seemed to have been aware of this fact when, in early 2017, Ross sailed through his Senate confirmation hearings. Informed by journalists about the revelations, Democratic Sen. Richard Blumenthal called for an investigation after saying Ross had misled Congress.

When contacted for a response last week, a Commerce Department spokesman did not dispute that Ross draws earnings from the Russian gas business, but he ruled out the possibility that this investment could have any influence on the commerce secretary’s mandate. He also confirmed that Ross served on Navigator’s board from 2012 to 2014. He said the decision to lease several ships to Sibur happened before that time and noted Sibur was not under sanctions when the contract was signed and that it is still not under sanctions today. The spokesman said Ross had never met the oligarchs Mikhelson, Timchenko or Shamalov.

To say Ross is a savvy businessman would be a gross understatement. The son of a lawyer and a teacher from New Jersey, Ross initially aspired to be a writer but discovered a passion for making money during an internship on Wall Street. For two decades, he managed Rothschild Inc.’s bankruptcy advisory business before striking out on his own. He bought up foundering companies, many in the steel and coal sectors, which he then restructured and sold. His skills earned him the moniker, the “King of Bankruptcy.”

In the eyes of many workers and even labor unionists, Ross was seen more as a savior who prevented worse things from happening at struggling companies than as a predator. Ross himself likes to boast that he has created or saved as many as 100,000 jobs. “There is virtually no part of the American economy in which he has not created jobs,” Republican Sen. Marco Rubio said at Ross’ Senate confirmation hearing last January. “This includes industries such as airplanes, apparel, auto parts, beer, banking, cards, electric utilities, food service, mortgages, oil and gas, rail manufacturing, shipping, textiles and trucking.”

Ross met Trump in the early 1990s, back when Trump was struggling to keep his Taj Mahal casino in Atlantic City afloat. Ross managed to convince other investors not to throw Trump out, arguing the Trump brand was still “very much an asset.” Since then, Ross and Trump have enjoyed many similarities. For one, they’re both billionaires and they’re practically neighbors in the ritzy beachside town of Palm Beach, Florida. And they both bill themselves as champions of an American working class, whose jobs they claim have been sacrificed through poorly negotiated trade deals. Ross likes to say he is “pro-trade,” but with a caveat: It has to be “sensible trade.”

In terms of his temperament, Ross is the antithesis to Trump’s braggadocio. During his four-hour hearing in the Senate in January, the septuagenarian sat quietly, patiently answering the senators’ questions.

Ross’ potential conflicts of interest were a central point of discussion. He had “some of the most extensive financial holdings of any nominees before this committee,” Democratic Sen. Bill Nelson said before praising Ross for agreeing to divest most of his personal holdings and resign from dozens of boards. “You are committed to doing the job the right way by placing the public’s interest ahead of your own,” Nelson said. Unaware of the revelations in the Paradise Papers at the time, Sen. Blumenthal was similarly effusive, even speaking of the “personal sacrifice” Ross had made.

But difficult questions were also asked. Ross had indicated that he intended to keep his stake in the company Diamond S Shipping, which operates 30 tankers. Democratic Sen. Maria Cantwell reminded Ross of the enormous environmental damage caused by the Exxon Valdez oil spill in 1989. Cantwell, who represents the northwestern coastal state of Washington, expressed doubt that Ross, as a shipping investor, could impartially regulate the maritime industry. “There are many, many, many, many aspects to your new job that will be about the regulation of this industry,” she said. Ross assured Cantwell and the other senators that he would recuse himself “where there’s the slightest scintilla of doubt.”

Ross is also vulnerable over his connections to Russia. For years, Ross was the vice chairman of the board at the Bank of Cyprus, a financial institution often used by Russian oligarchs. After Ross’ hearing in the Senate, five Democratic senators demanded clarification about Ross’ involvement with Cyprus’ largest financial institution. “The United States Senate and the American public deserve to know the full extent of your connections with Russia and your knowledge of any ties between the Trump Administration, Trump Campaign, or Trump Organization and the Bank of Cyprus,” wrote Democratic Sen. Cory Booker. A response from Ross was not forthcoming.

"Why would any officer of the U.S. government have any relationship with a Putin crony?" Dan Fried, expert on Russia

None of the senators present at Ross’ confirmation hearing asked about Navigator. The impression in Washington appeared to be that the incoming commerce secretary had severed his ties to the company. It was well known that Ross had invested in Navigator in 2011 and had soon become a majority stakeholder with a seat on the board of directors. That was also when the business relationship with the Russian gas company Sibur came about. But in 2014, Ross stepped down from Navigator’s board, and by the time he was tapped to lead the Commerce Department in 2016, it seemed like he was going to divest his shares as well.

Having a close relationship with Russia has not always been a problem for American business leaders. For a while, it was even desirable. President Bill Clinton, a Democrat, once nominated Ross to head the U.S. Russia Investment Fund, which promised to facilitate détente after the Cold War while raking in profits, particularly through lucrative joint ventures in the energy sector. Some of Trump’s other cabinet secretaries have also pursued deals with Russia’s oil and gas industry – most notably Rex Tillerson, the former CEO of ExxonMobil and current U.S. secretary of state.

But the illegal annexation of Crimea ordered by Putin in 2014 complicated the situation. The U.S. and the European Union responded with punitive sanctions against Russia. These do not have a direct impact on Russian gas exporter Sibur, but they presumably do affect some of its stakeholders and their other companies. One Sibur shareholder, Timchenko, had sanctions imposed against him by the U.S. shortly after Crimea was annexed because his “activities in the energy sector have been directly linked to Putin,” the Treasury Department (then still under President Obama) wrote at the time. Another shareholder, Mikhelson, may not have been targeted personally by sanctions, but his company, natural gas producer Novatek, was. Meanwhile, Navigator Holdings did not scale back its business ties with Sibur once sanctions were unveiled. On the contrary: From 2014 to 2015, the percentage of Navigator’s total revenues derived from Sibur grew from 5.3 to 9.1 percent, and the share for 2016 was 7.9 percent. That makes the Russian company, along with PDVSA, Venezuela’s state-owned oil company, Navigator’s most important clients.

Sibur is a prime example of “a company with crony connections,” argues Dan Fried, a retired American diplomat and an expert on Russia. "Why would any officer of the U.S. government have any relationship with a Putin crony?" he asked.

During Ross’ confirmation hearing last January, one of the senators confronted him with a hypothetical question: If Trump had business interests, such as a hotel or a golf course, in a certain country, the politician asked, would it give that country undue leverage over the president? Say, if the government in question threatened to close the hotel or golf course? Or, could Trump be enticed with the prospect of commercial favors? Could Trump ever find himself in a situation in which his business interests might cause him to make concessions to a foreign government, for instance, on trade agreements? Ross answered that Trump was not the sort of person who let himself be blackmailed or intimidated.

The new information from the Paradise Papers about Ross’ business ties to Russia also begs another question: How is Ross supposed to make impartial decisions about trade policies, regulations or sanctions if those decisions ultimately affect his own business interests?