A U.S. official with direct knowledge of Russian counterintelligence investigations noted that while other oligarchs had ties to Russian organized crime or sought to connect with elements of it for business purposes, the U.S. had no evidence Vekselberg ever engaged with the Russian mob.

Vekselberg is now one of the world’s 100 richest men, with a current net worth of $15.5 billion, according to the Bloomberg Billionaires Index. He has consolidated his businesses under the Renova Group umbrella, with oil, metals and telecommunications components.

He has won plaudits for his art collection, which includes Faberge eggs, designed for the czars as Easter gifts. As a patriotic gesture, he bought them and repatriated them to Russia. The Imperial Easter eggs were purchased at a reported cost of $100 million.

Michael McFaul, a former U.S. ambassador to Russia, said of Vekselberg: “I would never describe him as being in the inner circle. He didn’t make his money under Putin. He made his money in the 1990s. But everyone has to make compromises. In fact, he has a complicated relationship with the Kremlin.”

One of the purloined U.S. diplomatic cables released by WikiLeaks in 2010 says that Vekselberg was critical of the Putin regime’s response to Russia’s economic woes during a 2006 meeting with one of McFaul’s predecessors as U.S. ambassador. “Prefacing his comments by saying, ‘I have great respect for our leaders, but …’ Vekselberg criticized the GOR’s response to the crisis,” said the cable, using an acronym for the government of Russia.

After the meeting, the U.S. ambassador wrote that Vekselberg “dismissed Russia’s hopes to become a major financial center as ‘not possible,’ and laughed off the idea, floated by Putin, of the ruble as a reserve currency.”

That’s not a surprise to McFaul, who said that Vekselberg was always more in tune with the less aggressive initiatives of Dmitri Medvedev, Putin’s prime minister, than the bombast of Putin. Medvedev and Vekselberg had worked together to build the Skolkovo Foundation, a technology and innovation center meant to help grow Russia’s cyber industry that Vekselberg now cochairs.

Yet Vekselberg has still supported Putin in very public ways. At a now infamous December 2015 dinner in Moscow honoring the 10th anniversary of RT, the Kremlin’s English language TV channel, he sat at the table next to Putin’s, a few feet away from the Russian president, future Trump national security adviser Mike Flynn and U.S. Green Party presidential candidate Jill Stein.

According to oligarch expert Seva Gunitsky of the University of Toronto, however, many observers were surprised he was sanctioned by the U.S. “He’s certainly not in Putin’s inner circle,” said Gunitsky, author of “Aftershocks: Great Powers and Domestic Reforms in the Twentieth Century.” “People call him Putin-connected and he’s connected to Putin like all the oligarchs are, he knows to throw money at Putin, but he’s not ‘connected’ like other oligarchs are connected.”

He also began to engage U.S. politicians. He gave the Clinton Foundation somewhere between $50,000 and $100,000, while his cousin Andrew Intrater, a U.S. citizen who is the CEO of Columbus Nova, contributed to the GOP and the Trump inaugural. Records show Intrater donated $29,600 to the Republican National Committee and $35,000 to the Trump Victory PAC in June 2017, and then $250,000 to the Trump Inauguration Fund.

Gunitsky believes Vekselberg is merely following the model that he and other oligarchs have used to survive in Putin’s Russia.

“He learned from what he saw happen in Russia,” said Gunitsky. “The best way to deal with politicians is give the government what it wants. He was applying his lessons of dealing with Putin in his dealings with Trump.”