Mikhail Prokhorov’s wealth is estimated at $10.2 billion, but a tiny portion of his assets — a media company with a market cap of just $32 million — is putting the rest of his Russian business at risk. President Vladimir Putin is willing to tolerate relatively independent media companies, as long as they’re small and don’t get too close to subjects that are uncomfortable for him. Prokhorov owns a popular media operation that has been too unafraid to show its teeth.

Prokhorov is something of a rarity among Russian billionaires. Cash and market investments make up almost half of his fortune, and the most expensive asset he controls is in the United States, not Russia — the Brooklyn Nets and the NBA team’s arena. Yet he has significant Russian assets, too, such as large stakes in Uralkali, the world’s biggest potash company, and Rusal, Russia’s No. 1 aluminum producer. That makes him hostage to Putin, who considers Russia’s billionaires — formerly known as oligarchs — merely as temporary holders of state property.

In 2012, Prokhorov ran for president against Putin and performed moderately well in Moscow. The degree of independence of his run was unclear, but his political ambitions were genuine. They have since been stymied by new regulations that banned politicians from owning any foreign assets. Yet, to the billionaire’s credit, he never used RBC, his media company, to further his political agenda. He has been an arms-length, almost disinterested owner since he acquired the company in 2010 for $80 million and restructured its $220 million in debt. His role largely has been limited to approving the hiring of experienced media managers and waiting for them to show results.

One of them was Derk Sauer, a citizen of the Netherlands who founded Russia’s first Western-style glossy magazines and business periodicals. Another was Elizaveta Osetinskaya, who had spent most of her professional life working for a Sauer-owned newspaper. (Disclosure: I worked for Sauer and with Osetinskaya in the 1990s and 2000s). Sauer, hired in 2012, began trimming expenses and fixing the business model at RBC. Osetinskaya, who joined in 2014 as editor in chief of all RBC properties — a news agency, a newspaper, a monthly magazine and a business-oriented TV station — led a leap in reporting quality and a monthly audience increase. The main site’s viewership increased to 12.9 million at the end of 2015 from 11.3 million in 2013. The company has been losing money but gradually paring the losses and outperforming the shrinking Russian media market.

Russia, however, is not the best place to be in the news business. Sauer had to step aside as president of RBC and move to Prokhorov’s holding company, Onexim Group, after some nationalist legislators assailed him for being a citizen of a hostile country. As of this year, foreigners are not allowed to own more than 20 percent of a media business, and international publishers, including Germany’s Axel Springer, Sweden’s Bonnier, the U.K.’s Pearson and U.S.-based Dow Jones, have sold their Russian properties cheaply because they were forced to get out.

Osetinskaya’s editorship turned out to be problematic for a different reason. Last year, RBC’s daily newspaper and website published an investigation into a huge real estate project involving Moscow State University. The publication traced the development to Katerina Tikhonova, who is widely reported to be Putin’s daughter, though the Kremlin hasn’t confirmed those reports. Another piece by RBC last year dealt with the career, and the story of remarkable enrichment, of Kirill Shamalov, who reportedly is Tikhonova’s husband. Shamalov allegedly received a loan from a bank controlled by a Putin crony to buy a large stake in the petrochemical holding Sibur, which made him a billionaire. And lately, RBC has been covering the Russia-related revelations from the Panama Papers, a huge leak of offshore accounts that shed light on some questionable dealings by Putin’s friends.

Putin likes to protect his private life, and above all the lives of his two daughters. In 2008, a Moscow newspaper was forced to cease operation days after publishing a story about Putin’s alleged relationship with the former rhythmic gymnastics champion Alina Kabaeva — which had been widely reported in Western tabloids. People familiar with the situation told me that the three stories, widely cited in Russia — RBC is the country’s 12th most-visited website — have angered Putin.

As the Russian president took questions from voters on April 14, operatives from the FSB secret police raided the offices of the Onexim Group and four of its subsidiaries, not including RBC. The raid took Prokhorov by surprise, but soon reports started surfacing in Russian media that Putin was taking a special interest in the billionaire’s assets after the RBC stories. An Onexim executive told me that he was “90 percent certain” the raid had been retribution for the investigations.

Suddenly, Prokhorov was under attack in pro-Kremlin media: His power-generating company, Kvadra, was accused of overcharging, and he was blasted for keeping much of his money offshore. There is a strong likelihood that after the raid, charges of tax improprieties will surface.

On Monday, the pro-Putin news site Gazeta.ru ran a story about Prokhorov preparing RBC and Kvadra for sale. The story said orders to sell had come from “on high.” Onexim has denied such plans and the Kremlin has denied that any such orders were given. “The Kremlin never interferes with editorial policy, much less property rights,” Putin’s spokesman Dmitri Peskov said, elicitng derision on the social networks.

Despite the denials, insiders at Prokhorov’s company feel that they are being warned — not necessarily to sell the media assets but perhaps to censor them to avoid angering Putin again. That would be consistent with the pattern of previous attacks on business leaders who defied Putin, such as the media tycoon Vladimir Gusinsky, the oil man Mikhail Khodorkovsky, the telecom billionaire Vladimir Yevtushenkov and the airport owner Dmitri Kamenshchik. For Khodorkovsky, it ended in imprionsment. Gusinsky suffered asset loss and was forced to emigrate.

Prokhorov is not going to be publicly ornery, as Gusinsky and Khodorkovsky were. Russian billionaires have learned their lesson. Osetinskaya, who was planning to leave for a year’s sabbatical at Stanford University, was pushed out on long-term leave at least a month earlier than intended. This sends a clear message to the staff: Even if the company is not sold, investigating Putin’s family and friends can be bad for the owner’s other, much more valuable businesses.

Putin now controls almost every wide-reaching news outlet in Russia through state ownership, his friends who have bought companies with the Kremlin’s backing or owners worried about their prospects in Russia. All he needs to do is jerk the leash from time to time.

Based in Berlin, Russian writer Leonid Bershidsky is a Bloomberg columnist.

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