Larry Ellison is on a buying spree, snapping up Paramount and CBS and eyeing CNN, HBO, and TikTok.

How did Ellison make his fortune? 
Through Oracle, the database, software, and cloud computing company he co-founded in 1977. Under Ellison, 81, the firm has grown into a nearly $900 billion tech colossus by devouring its rivals and trying to destroy those it couldn’t buy out. During a brutal competition with Microsoft in the 1990s for control of the database and enterprise software markets, Oracle hired private investigators to dig through the trash of a pro-Microsoft trade group. “It’s not enough that we win; all others must lose,” Ellison has said, paraphrasing Genghis Khan. Ellison, who grew up poor on the South Side of Chicago and is now the world’s second-wealthiest person, has used his $350 billion fortune to pursue a string of passion projects. The six-times-married Oracle chairman has bought up 98% of the Hawaiian island of Lanai; spent more than $750 million competing in the America’s Cup yacht race, which he’s won twice; donated more than $350 million to research on aging and age-related diseases; and staged mock dogfights over the Pacific Ocean in military-style jets with his son, David. Business writer and former Wall Street banker William D. Cohan said Ellison is now focused on a different passion project, becoming “one of the most powerful media and entertainment moguls America has ever seen.” 

How is he trying to do that? 
It started with this summer’s $8 billion merger between David’s production company, Skydance, and Paramount, owner of CBS, Showtime, and movie studio Paramount Pictures. That deal was largely bankrolled by Ellison. Then in September, Trump signed an executive order that would transfer ownership of TikTok’s U.S. operations—and access to the social media app’s 170 million American users—from Chinese parent company ByteDance to a group of American investors, including Oracle. That deal, valued at about $14 billion, is awaiting approval from Beijing. Paramount Skydance has also bought center-right news startup The Free Press, which has railed against the “wokeism” of the mainstream media, for $150 million. And the Ellisons are now reportedly preparing a bid of up to $80 billion for Warner Bros. Discovery, home of CNN, HBO Max, and the Warner Bros. movie studio. Collectively, those deals could give the Ellisons even more influence than the Murdoch family. Many critics are worried about how the Ellisons will wield that power. 

Why are they concerned? 
Because of the closeness between Ellison and Trump. Once a major backer of President Bill Clinton, Ellison shifted to the right under President Barack Obama, viewing the Democrat as hostile to Israel. (Ellison is Jewish.) The tech billionaire hosted a fundraiser for Trump’s re-election campaign at his Rancho Mirage, Calif., estate in February 2020, and that year Trump supported Oracle’s attempt to buy TikTok’s American operations with Walmart, a deal that ultimately fell through. In November 2020, Ellison joined a phone call where Trump staffers and supporters discussed strategies to challenge the president’s defeat at the ballot box; David Ellison later said his father believed Joe Biden won the election. A day after Trump’s second inauguration, Ellison appeared at the White House with OpenAI CEO Sam Altman to announce a $500 billion AI data center venture known as Stargate. Trump described Ellison at the event as “sort of CEO of everything,” and since then the pair have held multiple private meetings. Given Ellison’s closeness to “the Trump regime,” said media watch group FAIR, the possibility of him owning CBS, CNN, and a major stake in TikTok “would be dangerous for democracy.” 

Has he pushed his media firms toward Trump? 
Signs of a move to the right can be seen at CBS News. David Ellison, 42, who describes himself as a “socially liberal person” and who donated nearly $1 million to President Joe Biden’s re-election campaign, has hired Free Press founder Bari Weiss as editor-in-chief of CBS News. It’s an unusual hire because Weiss is an opinion journalist with no TV news experience. To win approval for the Paramount-Skydance merger from FCC chair and staunch Trump ally Brendan Carr, David installed the former head of a conservative think tank as an ombudsman at CBS News to evaluate complaints of “bias” at the network. Trump said last week that he believes CBS News will become “fairer” under its new management. Following Carr and Trump’s attempt to get late-night host Jimmy Kimmel fired by Disney, some in Hollywood worry that the Paramount takeover could lead to movie and TV writers being ordered to avoid subjects that might anger Trump and the MAGA right. “What kind of chilling effect could the Trump administration’s demand for a conservative viewpoint have on entertainment?” an unnamed screenwriter told Vanity Fair. “It’s a four-alarm fire, and we ignore it at our peril.” 

Are those fears justified? 
It’s not yet clear. David Ellison has said that he does “not want to politicize our company in any way, shape, or form,” and his main interest appears to be Paramount’s entertainment wing, not its news business. And some industry observers note that the Ellisons may be trying to appease Trump not out of ideological fealty but because they see a one-off opportunity to build a media colossus that would typically be blocked on antitrust grounds. “Who knows how long they will have the administration’s ear?” said Paul Hardart, a media expert at New York University’s Stern School of Business. By combining TikTok’s algorithmic approach to entertainment with Paramount’s massive audience and media franchises, the family could create an entirely new kind of media business. “You have a son who is going into media, a father who is close to Trump and acquiring the most addictive social platform we’ve ever seen,” said Anthony Palomba, a communications and business specialist at the University of Virginia. “These are very smart people, and none of this is accidental.”

Like father, like son? 
David Ellison’s Hollywood adventure began with a flop. An aspiring actor and a skilled stunt pilot, he made his movie debut in the 2006 World War I drama Flyboys—which he also co-produced. Flyboys crashed, grossing less than $18 million at the box office and never recouping its $65 million budget, which was funded largely by his father. Ellison had more success after moving off-screen. Skydance scored its first hit in 2010 with the Oscar-winning Western True Grit, and David has since helped engineer numerous box office smashes, including 2022’s Top Gun: Maverick. Those close to him say David’s passion for movies is real, and many in Hollywood hope that by acquiring Paramount he can help lure back viewers captured by YouTube and other tech interlopers. But perhaps his greatest asset is his father’s vast fortune. “Our largest shareholder is the second-richest person in the world,” said Paramount president Jeff Shell. “That seems like a good thing.”

Even for a jaded old political warrior like me, said William Kristol in The Bulwark, last weekend’s nationwide “No Kings” protests were deeply moving. In what was likely the largest single protest in the nation’s history, some 7 million people “assembled peacefully and patriotically” in major cities and rural towns like Macon, Ga., and Plano, Texas, “to protest Donald Trump and reaffirm their allegiance to the American idea.” The rallies had an inspiring mood of both “joy and sobriety,” and were an emphatic rejection of Trump’s assault on the rule of law and the Constitution. Republicans had ludicrously predicted that No Kings would be violent gatherings of antifa radicals who “hate America,” but the rally’s “obvious success” triggered Trump. He posted a childish video of a jet emblazoned with “KING TRUMP” dumping torrents of excrement on the protesters. In interviews, he ominously warned that he could invoke the Insurrection Act in response to large protests—an indication he finds dissent intolerable. 

Trump has good reason to be threatened by No Kings, said Jamelle Bouie in The New York Times. His growing authoritarian control of the nation depends heavily on the perception that he’s “the authentic tribune of the people.” The images of millions of outraged Americans filling the streets presents “a direct rebuke” to that narrative, revealing he’s “far from as popular as he says he is.” To diminish the protests, Republicans also tried laughing them off as “middle-aged-women coded,” said Quinta Jurecic in The Atlantic. All those “wine moms” and gray-haired people with punny anti-Trump signs reminding America of our democratic ideals, the Right claimed, were earnest, uncool, “cringe”—in contrast to the cynical, macho MAGA ethos. But as idealistic as it was, the massive show of defiance struck an important blow against fatalism, and could help rally disheartened voters to organize to defeat Trump and his allies. 

No Kings was a good start, said Ronald Brownstein in Bloomberg, but “to convey the urgency of the moment,” the loyal opposition needs “an edgier tool”: a general strike. Millions of workers across multiple sectors of the economy could withdraw their labor for days. General strikes can create attention, urgency, and solidarity, and were effectively used to defeat autocracy in Poland and Brazil. Discussion of this strategy among Trump’s opponents “is intensifying—as a supplement, not a substitute, to mass public protest.”

Jennifer Aniston’s reproductive choices have been a media obsession for decades, said Frances Hedges in Harper’s Bazaar. Through the 2000s, tabloids ran seemingly endless stories on whether the Friends star was or was not pregnant. And when Aniston and Brad Pitt announced their divorce in 2005, rumors quickly circulated that the split was the result of Aniston prioritizing her career over starting a family. In fact, she’d been going through IVF—unsuccessfully—but stayed quiet because she didn’t want to give gossip columnists more material. 

Then in 2016, she decided to speak out in a Huffington Post op-ed slamming the media’s “lies” and “dehumanizing” views of women. “They didn’t know what I’d been going through over the past 20 years to try to pursue a family, because I don’t go out there and tell them my medical woes,” says Aniston, 56. “That’s not anybody’s business. But there comes a point when you can’t not hear it: how I won’t have a baby, won’t have a family, because I’m selfish, a workaholic. It does affect me—I’m just a human being.” Aniston is happy that the tabloid press has lost much of its power, but thinks the cruelty that once lived on the printed page has simply moved to social media. “I’m sure the guys who came up with it thought it was a great idea, and yeah, congratulations on your billions, but it has taken down a huge portion of humanity.”