Commerce Secretary Wilbur Ross has business ties to members of Russian President Vladimir Putin’s inner circle — but he didn’t properly reveal that information to the government.

It turns out that Ross’s investment firm has a 31.5 percent stake in Navigator, a British company that charters ships to help energy companies move their materials around the world. One of Navigator’s top clients is the Russian energy giant Sibur, whose owners include Gennady Timchenko — Putin’s friend and judo partner who is sanctioned by the United States — and Putin’s son-in-law Kirill Shamalov.

This is a big deal because it’s the first time a member of President Donald Trump’s Cabinet has been directly linked through business to Putin’s family or confidants. The revelation came to light after the German newspaper Süddeutsche Zeitung received documents and other data in the second-largest data leak in history, known as the “Paradise Papers,” that shows how around 120 global politicians and leaders keep their money in offshore tax havens. The data was then shared with the International Consortium of Investigative Journalists and global outlets.

Among the 13.4 million files are about 7 million from Appleby, a top offshore law firm. Some of those documents lay out how Appleby helped Ross secure his money in the Cayman Islands and administered his assets in more than 50 companies and partnerships.

Ross denies any wrongdoing, and a statement from the Commerce Department says he “was not involved with Navigator’s negotiations to engage in business with Sibur.” It also says he disclosed his Navigator holdings, which can be found online.

But the news will raise even more eyebrows in Washington just a week after special counsel Robert Mueller’s probe into possible Trump-Russia collusion during the 2016 election charged three of Trump’s campaign staffers. And while it doesn’t appear Ross broke any laws, the connection with Russia isn’t a good look for an administration battling its own Russia problems.

“When you start doing business with Russian energy companies like Gazprom and Sibur, you’re not just getting into bed with the company,” Amos Hochstein, a top energy diplomat in the Obama administration, told the New York Times. “You’re getting into bed with the Russian state.”

“A company with crony connections”

In November 2011, Ross’s company WL Ross & Co. invested in two shipping companies: Diamond S Shipping and Navigator Holdings. (Ross was on Navigator’s board at least until March 2012, and the company acquired a majority stake in Navigator in August 2012.) Ross hoped both Navigator and Diamond S would soon pursue opportunities in Russia and China, the New York Times reports. In early 2012, Navigator began chartering ships for a Russian energy company called Sibur.

Sibur was once a state-run company, but in 2010 the government sold it to Putin’s friend Timchenko and Leonid Mikhelson, who is also Kremlin-connected. They were both placed on the US Treasury’s sanctions list in 2014 because of Russia’s annexation of Crimea and their ties to Putin. Despite its technical independence, Sibur still needs help from Moscow and is therefore both loyal and friendly to the Putin regime.

Shamalov, who married Putin’s youngest daughter Katerina in 2013, also bought part of the company. With the help of a $1.3 billion loan from Moscow-controlled Gazprombank, Shamalov invested enough in September 2014 to own 20 percent of Sibur.

Having Timchenko and Shamalov leading the organization made it “a company with crony connections,” Daniel Fried, a Russia and sanctions expert and former top US diplomat, told the New York Times.

The Navigator-Sibur relationship really took off in 2014, despite the sanctions. Their business relationship proved quite lucrative for Navigator, which collected around $68 million in revenue from Sibur since 2014.

But the sanctions pressure eventually weighed on Timchenko, who subsequently sold a 17 percent stake in the company to a junior shareholder. Shamalov also reduced his share and now owns around 3.9 percent after selling part of his stakes in April. Much of these financial moves happened in Cypriot banks, where Timchenko and Mikhelson held Sibur investments.

Interestingly, Ross became the vice chair of the Bank of Cyprus in the summer of 2014 — a bank with known money laundering issues and connections to Russian oligarchs. The Commerce Department says Ross has never met Timchenko, Mikhelson, or Shamalov, and there is currently no indication that they interacted while Ross held his position at the bank.

Ross resigned his vice chairmanship with the Bank of Cyprus on March 1 after he became the secretary of commerce.

“The American people were misled”

Ross has had connections to Russian businesses for a long time. In the 1990s, then-President Bill Clinton named Ross to the board of the US Russia Investment Fund, which was meant to help improve US business ties in Russia.

So it’s no surprise that Ross would have business relationships with Russia. The problem is he wasn’t very forthcoming with the government about his Navigator relationship. As part of his confirmation process, he filed an ethics agreement on January 15 to the Commerce Department that listed the companies he intended to hold on to, which he valued between $2.05 million and $10.1 million. That step helped Ross persuade members of Congress to confirm him, because they worried he might face many conflicts of interests since he had stakes in hundreds of companies and sectors.

Vitally, he didn’t disclose all the investments that were included in those companies. Navigator, and the 17.5 million shares Ross had in it, was one of those undisclosed investments. Ross did mention Navigator in another document that outlined his holdings up to December 2016, but it didn’t reference the company’s ties to Sibur.

However, disclosure rules don’t say he had to declare his interest in Navigator. The Office of Government Ethics ultimately approved Ross’s disclosures. Today, Ross recuses himself from anything regarding transoceanic shipping, a Commerce Department spokesperson said in a statement.

But some members of Congress feel they didn’t get the full picture of Ross’s ties to Russia during the debate over his confirmation. “I am astonished and appalled because I feel misled,” Sen. Richard Blumenthal (D-CT), a member of the Commerce Committee, told NBC News. “Our committee was misled, the American people were misled by the concealment of those companies.” Blumenthal has now called for an investigation into the matter.

Government ethics experts also feel Ross didn’t disclose enough. “The information that he provided on that form is just a start. It is incomplete,” Kathleen Clark, an expert on government ethics, told NBC News. “I have no reason to believe that he violated the law of disclosure, but in order … for the Commerce Department to understand, you’d have to have more information than what is listed on that form.”

It’s still unclear exactly why Ross omitted the information. But what seems clear is that the Trump administration’s ties to Russia are far stronger than originally thought.