After becoming commerce secretary, Wilbur Ross Jr. retained investments in a shipping firm he once controlled that has significant business ties to a Russian oligarch, according to newly disclosed documents.

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After becoming commerce secretary, Wilbur Ross Jr. retained investments in a shipping firm he once controlled that has significant business ties to a Russian oligarch subject to U.S. sanctions and President Vladimir Putin’s son-in-law, according to newly disclosed documents.

The shipper, Navigator Holdings, earns millions of dollars a year transporting gas for one of its top clients, a giant Russian energy company called Sibur, whose owners include the oligarch and Putin’s family member. Despite selling off numerous other holdings to join the Trump administration and spearhead its “America first” trade policy, Ross kept an investment in Navigator, which increased its business dealings with Sibur even as the West sought to punish Russia’s energy sector over Putin’s incursions into Ukraine.

Partnerships used by Ross, whose private equity firm has long been the biggest shareholder in Navigator, have a 31 percent stake in the company. Though his personal share of that stake was reduced as he took office in February, he retained an investment in the partnerships valued between $2 million and $10 million, and stood to earn a higher share of profits as general partner, according to his government ethics disclosure and securities filings.

Ross’ stake in Navigator has been held by a chain of companies in the Cayman Islands, one of several tax havens where much of his wealth, estimated at more than $2 billion, has been tied to similar investment vehicles. Details of these arrangements surfaced in a cache of leaked files from Appleby, one of the world’s largest offshore law firms, which administered some 50 companies and partnerships in the Caymans and elsewhere connected to Ross.

The Appleby documents, obtained by the German newspaper Suddeutsche Zeitung, were shared with the International Consortium of Investigative Journalists and other media organizations, including The New York Times. They show how the Bermuda-based Appleby worked to help the wealthy elite, from Russian oligarchs to Middle Eastern princes, as well as multinational corporations like Apple and Nike, avoid billions of dollars in taxes.

In addition to Ross, the files contain references to other members of the Trump administration, including Gary D. Cohn, the chief economic adviser who was associated with 22 Bermuda entities while an executive at Goldman Sachs, and Secretary of State Rex Tillerson, who was a director of a Bermuda-based joint venture with the government of Yemen when he ran Exxon Mobil’s operations there. There is no evidence of illegality in any of their dealings.

Ross emerges as a particularly valued client for the offshore law firm, whose records provide more insight into his financial holdings beyond the public ethics disclosures he made upon joining the Trump administration. His ethics agreement filed in January listed the partnerships he intended to keep, but not the investments they held. Previously, Navigator had been mentioned in a separate, 57-page description of his holdings for the year that ended in December 2016, but with no hint of its ties to Sibur.

Sibur’s top ownership — including Gennady Timchenko, who is Putin’s friend and judo partner and is subject to U.S. sanctions, and Kirill Shamalov, who is married to the Russian president’s youngest daughter — makes it “a company with crony connections” in Moscow, said Daniel Fried, a Russia expert who served in senior State Department posts in Republican and Democratic administrations.

Another of Navigator’s major customers is PDVSA, the Venezuelan state oil company, controlled by the authoritarian regime of Nicols Maduro. The Trump administration imposed sanctions on PDVSA this summer.

In a written response to questions by the Times, James Rockas, a spokesman for Ross, said that Navigator’s relationship with Sibur began before Ross joined the board in March 2012, and that he had never met the Russian oligarchs who are Sibur’s major shareholders. Public records show that Ross’ firm became a major investor in Navigator in November 2011, three months before the company chartered its first ships to Sibur.

“Sibur was not under sanctions at the time the contract was signed and is still not subject to sanctions,” Rockas said.

More broadly, he said that Ross “recuses himself from any matters focused on transoceanic shipping vessels, but has been generally supportive of the administration’s sanctions of Russian and Venezuelan entities.”

“Secretary Ross has never had to seek, nor received, any ethics exemption,” Rockas said, “and he works closely with Commerce Department ethics officials to ensure the highest ethical standards.”

It is perhaps unsurprising that Navigator would have a relationship with a major Russian company during Ross’ tenure. Much like President Donald Trump, whose company sought approval for a hotel project in Moscow as recently as last year, Ross has long shown an appreciation for the untapped potential of Russian markets when seeking investment opportunities. His involvement there dates at least to the 1990s, when he was appointed by President Bill Clinton to the board of the U.S. Russia Investment Fund, established to promote U.S. business interests in Russia.

Since then, in addition to Navigator, his firm acquired a German rail-car company, VTG, which pursued an expansion strategy in Russia before Ross sold his stake in 2016. And Ross led a private bailout of the Bank of Cyprus, long regarded as a favorite financial haven of wealthy Russians, after the worldwide economic crisis crippled the Cypriot banking system.

In the wake of reports of Russian interference in the U.S. presidential election, multiple investigations have explored potential business ties between Russia and members of the Trump administration. While several Trump campaign and business associates have come under scrutiny, until now no business connections have been reported between senior administration officials and members of Putin’s family or inner circle.

During Ross’ confirmation process, he was asked repeatedly about his business ties to Russia, mostly related to his former role as vice chairman of the Bank of Cyprus, where he dealt with Russian investors but also forced some of them out of the bank. He was also asked about his investment in another shipping company, Diamond S, and whether its dealings with China could pose a conflict with his government duties. But he faced no questions about Navigator and its significant financial relationship with Sibur.

Rockas did not respond to questions about the current status of Ross’ investment. If Ross stands to benefit, albeit indirectly, from a Russian firm controlled by members of Putin’s inner circle, it poses a potential conflict with his role as the lead Cabinet member on trade policy, ethics experts said. Richard Painter, who served as chief ethics lawyer in the George W. Bush White House and has emerged as a frequent critic of the Trump administration, said that while Ross’ continued investment in Navigator would not violate any laws, it created other ethical concerns.

“Apart from those legal issues,” Painter said, “I’d be very concerned that someone in the U.S. government was making money from dealing with the Russians.”

As for Navigator, its leadership sees blue skies ahead with one of its key investors now at the helm of U.S. trade policy.

On Nov. 30 of last year, hours after being nominated as commerce secretary, Ross celebrated at Gramercy Tavern, an upscale Manhattan restaurant, at an event hosted by Navigator. He and David J. Butters, Navigator’s chief executive, arrived early to a private room and had a chat.

“Your interest is aligned to mine,” Butters recalls Ross saying, according to Bloomberg Businessweek. “The U.S. economy will grow, and Navigator will be a beneficiary.”