Twitter is a critical source of information—not just for ordinary users, but for activists and media professionals as well. In announcing his intent to buy the social media platform earlier this month, the Tesla CEO said he wanted to make Twitter a “platform for free speech around the globe.”

But in recent years, the number of people left in control of free speech appears to have dwindled as billionaires scoop up legacy media properties in multimillion deals—all now dwarfed by Elon Musk’s massive investment in Twitter. (Other social media giants like Meta and Alphabet are, at least, still public companies.)

Here are how some of those billionaire acquisitions have played out.

Billionaires buying newspapers

Amazon founder Jeff Bezos’s $250 million purchase of the Washington Post from the Graham family in 2013 arguably sparked the most recent wave of media acquisitions. Bezos’s purchase has been credited with revitalizing the paper, which tripled its web traffic and returned to profitability within three years.

Two years after Bezos moved on the Washington Post, China’s Alibaba Group, founded by Jack Ma, announced plans to purchase Hong Kong’s century-old South China Morning Post for $226 million, taking ownership from Kerry Media, run by the Malaysian Kuok family. 

Ma said his goal in buying the SCMP was to leverage Alibaba to “help the paper report on Asia and China more accurately compared with other media who have no such access”—a view that has led some outside observers to criticize the paper for being too soft on China since the purchase.

Like Bezos did with the Post, the SCMP’s new owners tried to revitalize the paper’s digital strategy, bringing in former Digg CEO Gary Liu to run the paper. Liu recently announced he was transitioning to run a new company spun off from the SCMP’s efforts to develop NFTs.

Billionaires have also purchased their “local” newspapers. In 2013, John Henry, owner of the Boston Red Sox (among several other sports teams) bought the Boston Globe from the New York Times Company for $90 million. Then, in 2018, Los Angeles–based biotech entrepreneur Patrick Soon-Shiong bought the Los Angeles Times and other Southern California newspapers from Tribune Publishing for $500 million in 2018.

But not every billionaire’s bid to buy a newspaper has panned out. In 2021, Maryland-based magnate Stewart Bainum offered to purchase Tribune Publishing to save it from the clutches of hedge fund Alden Global Capital. Observers had hoped that Bainum would be a better steward of Tribune’s newspapers than Alden, which has a reputation for aggressive cost cutting. However, Bainum’s offer fell apart after a major backer pulled out, and Tribune was sold to Alden in May 2021.

Magazine racks

Some billionaires appear to prefer glossy mags over stiff broadsheets.

In 2017, Laurene Powell Jobs, widow of Apple cofounder Steve Jobs, bought The Atlantic from the National Journal Company in 2017 for an undisclosed stake. Jobs made the investment through the Emerson Collective, a private company she founded to support social entrepreneurs and organizations.

The unwinding of Time Inc. in 2018 also presented an opportunity for billionaires to pick up some of the U.S.’s oldest magazines including Time, which was bought by Salesforce cofounder Marc Benioff for $190 million in September 2018, and Fortune, which was acquired by Thai billionaire Chatchaval Jiaravanon for $150 million a month later.

Media empires

Then there are all the businesspeople who made their fortunes from media, rather than entering the industry after finding success elsewhere.

Prime among them is Rupert Murdoch, with a net worth of $20 billion, according to Forbes. Murdoch made his wealth from News Corporation, the publishing and media behemoth that owns properties like the Wall Street Journal, Fox News, and publisher HarperCollins. 

The Springer family also made their fortunes from media. The family owes their wealth to the German media conglomerate Axel Springer, which owns German publications like Die Welt and Bild as well as global properties like Politico and Insider.

But perhaps the wealthiest billionaire to make his fortune, at least in part, from media is Michael Bloomberg, founder of Bloomberg LP, with a net worth of $82 billion, according to Forbes. Bloomberg’s eponymous company began as a financial information service in 1982 but launched a news division in 1990 to deliver financial stories to Bloomberg Terminal subscribers. Now Bloomberg is one of the primary sources of news for readers worldwide.