Obscured by a maze of offshore shell companies, the Twitter investment was backed by VTB, a Russian state-controlled bank often used for politically strategic deals. And a big investor in Mr. Milner’s Facebook deal received financing from Gazprom Investholding, another government-controlled financial institution, according to the documents. We are making money for our limited partners, and we are giving money back to them. While it is unclear precisely when Kanton first received its stake in the DST entity, Kanton received $197 million of the Gazprom Investholding loans three months before Facebook announced its first deal with Mr. Milner, the records show. Mr. Usmanov, he said, “did not borrow from or use state or quasi-state funds to make investments in Facebook.” The Facebook deal was a case study in the way Russia’s oligarchs have mixed public and private roles for their own, and their government’s, benefit: Even as he was investing in Facebook, Mr. Usmanov was general director of Gazprom Investholding. Kroll investigators found that, for some investments, Mr. Usmanov turned to Kanton, the company that would be a part of Mr. Milner’s Facebook investment. On May 7, 2014 — six months after Twitter’s initial public offering, when insiders were first permitted to sell their shares — VTB transferred the bulk of its stake in DST Investments 3 to Kanton. DST also cashed out its Twitter investment. investors. Mr. Milner said he invested $850,000 in Cadre through a trust, which in turn controls DST Global Advisers, DST Global’s investment management firm.
In fall 2010, the Russian billionaire investor Yuri Milner took the stage for a Q. and A. at a technology conference in San Francisco. Mr. Milner, whose holdings have included major stakes in Facebook and Twitter, is known for expounding on everything from the future of social media to the frontiers of space travel. But when someone asked a question that had swirled around his Silicon Valley ascent — who were his investors? — he did not answer, turning repeatedly to the moderator with a look of incomprehension.
Now, leaked documents examined by The New York Times offer a partial answer: Behind Mr. Milner’s investments in Facebook and Twitter were hundreds of millions of dollars from the Kremlin.
Obscured by a maze of offshore shell companies, the Twitter investment was backed by VTB, a Russian state-controlled bank often used for politically strategic deals.
And a big investor in Mr. Milner’s Facebook deal received financing from Gazprom Investholding, another government-controlled financial institution, according to the documents. They include a cache of records from the Bermuda law firm Appleby that were obtained by the German newspaper Süddeutsche Zeitung and reviewed by The Times in collaboration with the International Consortium of Investigative Journalists.
Ultimately, Mr. Milner’s companies came to own more than 8 percent of Facebook and 5 percent of Twitter, helping earn him a place on various lists of the world’s most powerful business people. His companies sold those holdings several years ago, but he retains investments in several other large technology companies and continues to make new deals. Among Mr. Milner’s current investments is a real estate venture founded and partly owned by Jared Kushner, President Trump’s son-in-law and White House adviser.
Facebook, Twitter and other social media sites have become a major focus of federal investigations into Kremlin interference in the 2016 election. Federal prosecutors and congressional investigators are examining how Russians linked to the Kremlin turned the sites into garden hoses of bogus news stories and divisive political ads, and whether they coordinated with the Trump campaign.
No one has suggested that Mr. Milner or his companies had any connection to the propaganda operation. For his part, Mr. Milner said in a pair of recent interviews that the Russian government money was no different from the financing he had received from his many other investors around the world.
Even so, his use of the state-directed apparatus employed by so many Russian oligarchs to enrich themselves shows how the Kremlin has extended its long financial arm not only to his company but to some of America’s technology giants.
“Kremlin-connected institutions make investments with strategic interests in mind — not just commercial interests but state interests as well,” said Michael Carpenter, the National Security Council’s Russia director in the Obama administration, who is now senior director of the Penn Biden Center for Diplomacy and Global Engagement. “They go hand in hand.”
Mr. Carpenter added, “Oligarchs who receive significant amounts of financial support from Russian banks like VTB or Sberbank or Gazprombank have to pass above a political threshold, meaning such support requires the explicit or tacit approval of those at the top of Russia’s crony capitalist system.”
There is nothing illegal about foreign state-owned institutions investing in American companies. VTB and Gazprom said the transactions were both sound investments, not motivated by political considerations.
As Mr. Milner sees it, the story is similarly simple — “nothing more than business,” he said, adding: “We are getting money, and we are putting them in Facebook and Twitter. We are making money for our limited partners, and we are giving money back to them. For me, it’s a commercial arrangement.”
Mr. Milner, 55, studied theoretical physics at Moscow State University before moving to the United States, where he attended the Wharton School at the University of Pennsylvania in the early 1990s and then worked for the World Bank in Washington.
He returned to Russia and in the late 1990s and worked as an executive at Bank Menatep, which was founded by Mikhail B. Khodorkovsky, the oil tycoon who was stripped of his company, prosecuted and imprisoned after a televised confrontation with President Vladimir V. Putin.
Mr. Milner eventually teamed with Alisher Usmanov — an Uzbek-Russian oligarch close to the Russian prime minister, Dmitri A. Medvedev — and a former Goldman Sachs executive to build a significant stake in Mail.ru, a Russian internet company that now trades on the London Stock Exchange.
Mr. Milner’s initial American investments came as he served on an innovation commission set up in 2009 by Mr. Medvedev, who was Russia’s president at the time and is something of a tech enthusiast, famously touring Apple’s headquarters in Cupertino, Calif., with Steve Jobs.
In May 2009, Facebook announced an investment of roughly $200 million by Mr. Milner’s company, Digital Sky Technologies, and said the company planned to spend at least $100 million buying additional stock. Eventually, Mr. Milner’s new venture capital firm, DST Global, also amassed a significant stake in Facebook.
“A number of firms approached us, but DST stood out because of the global perspective they bring,” Mark Zuckerberg, Facebook’s chief executive, said at the time.
The documents reviewed by The Times reveal that DST brought something else as well: a connection — through a succession of shell companies — to the Kremlin.
In those years, as part of its diplomatic “reset” with Moscow, the Obama administration was encouraging Russia to learn from the American technology industry. Importing tech knowledge, the theory went, would ease Russia’s dependence on exporting oil and gas.
For the Facebook deal, it was Gazprom, the state-controlled natural-gas giant, that became the bridge. The company, a vital component of the Putin government has employed its financial subsidiary, Gazprom Investholding, to reclaim assets privatized during the 1990s.
Gazprom Investholding is “used for politically important and strategically important deals for the Kremlin,” said Ilya Zaslavskiy, a contributor to the Kleptocracy Initiative, a project of the Hudson Institute, a conservative think tank in Washington. Both VTB and Gazprom Investholding’s parent, Gazprom, are under United States sanctions stemming from Russia’s support of separatists in eastern Ukraine in 2014.
Over several years, Gazprom Investholding and a subsidiary made hundreds of millions of dollars in loans to a company called Kanton Services, according to records from the Panama Papers, the trove of leaked documents from the law firm Mossack Fonseca. Kanton, in turn, owned one of the DST investment vehicles used to buy shares of Facebook. While it is unclear precisely when Kanton first received its stake in the DST entity, Kanton received $197 million of the Gazprom Investholding loans three months before Facebook announced its first deal with…