How Jeff Bezos Went to Hollywood and Lost Control

Jeff Bezos amassed the world’s greatest fortune by relying on what he has called a “regret minimization framework.” He built an $800 billion company with 14 codified principles and a brutally exacting culture. His annual salary of $81,840 has not budged since 1998.

But then Mr. Bezos went to Hollywood.

In the weeks since the Amazon founder tweeted that he and his wife of 25 years were divorcing, he has gone to war with a grocery store tabloid and escalated a conflict with the president of the United States. And he has essentially ceded control of his own narrative to two rogue characters: a swashbuckling A-list security consultant, Gavin de Becker, and his girlfriend’s fame-hungry brother-manager, Michael Sanchez. Locked in a feud, the two are prolonging the scandal’s news value almost daily.

Mr. Bezos is at the center of an honest-to-God melodrama, full of salacious revelations, family betrayals and international intrigue. In Seattle, Amazon’s senior vice president for global corporate affairs, the former White House press secretary Jay Carney, has recently tried to get the story back under control. But in Hollywood, the swirl around Mr. Bezos’s love life refuses to be contained, churning through an ecosystem of gossip and favors, where dish on the rich and powerful is currency.

Amazon executives were blindsided by a sequence of events that began in early January: the announcement by Jeff and MacKenzie Bezos of their divorce; the 11-page National Enquirer exposé that Mr. Bezos was romantically involved with Lauren Sanchez, a former Los Angeles TV anchor; a sensational blog post by Mr. Bezos accusing the head of the tabloid, an ally of President Trump, of attempting to extort him over a “below-the-belt selfie” and other sexts.

It has not helped matters that the intimate details of Mr. Bezos’s personal life emerged around the same time that the company abruptly canceled its plans to build a new headquarters in New York, after fighting with lawmakers and activists. People who have worked closely with Mr. Bezos have watched dumbfounded that a man famous for being a vault of discretion could end up, as one of them put it, in the middle of such a “clown show.”

For advice on the crisis, Mr. Bezos has relied almost entirely on Mr. de Becker, who in addition to providing security to stars is something of a celebrity himself. He once protected Cher, and he delivered a eulogy at the memorial of his friend Carrie Fisher. His book, “The Gift of Fear,” was a megahit — Oprah Winfrey backed it — and reads like a TED Talk for the rich and afraid.

Mr. de Becker is employed by Mr. Bezos, not Amazon, and appears to be hardly in touch with strategists at the company. Adding to the cast, Mr. de Becker has enlisted the famed law firm Boies Schiller Flexner, as well as Marty Singer, a notorious Los Angeles litigator who has represented John Travolta and Sharon Stone, to work the media.

Ms. Sanchez has consulted the Los Angeles divorce maestro Laura Wasser, who has counted Kim Kardashian West and Angelina Jolie as clients. Also in the mix is Ms. Sanchez’s estranged husband, Patrick Whitesell, who as the executive chairman of Endeavor is one of the most powerful figures in Hollywood. His business partner at the agency is the operatically colorful macher Ari Emanuel, and they know more than almost anyone about how to use tabloid ink to boost a client or break a competitor.

After the affair broke into the open, it didn’t take long for Mr. Whitesell to be spotted by TMZ leaving a nightclub with a 20-something model. Her surname? Alexa.

An expanding cast of only-in-L.A. characters

The loosest cannon of them all may be Michael Sanchez. Ms. Sanchez’s brother is a scrappy agent to a roster of reality TV personalities and an incorrigible gossip even in a town full of them. He is also a supporter of Mr. Trump, and has relationships with some of his operatives, including Roger Stone and Carter Page. Mr. Sanchez is in regular touch with an expanding list of reporters around the country, and is constantly supplying them with fresh innuendo on the Bezos drama.

Mr. Sanchez alleges that Mr. de Becker is trying to keep his sister away from Mr. Bezos, in hopes of keeping the Bezos marriage intact. “Gavin has brilliantly set you and I up with the clear goal of destroying your love for my sister,” Mr. Sanchez wrote in an email to Mr. Bezos on Valentine’s Day, a copy of which was reviewed by The New York Times. “I know the truth about your love for Lauren and her love for you.”

Four people with direct knowledge of the siblings’ relationship said that Ms. Sanchez is no longer speaking to her brother. Mr. Sanchez disputed this, and Ms. Sanchez declined to comment.

In February, The Daily Beast reported that Mr. de Becker had completed an investigation into who initially leaked the texts, and that Mr. Sanchez provided The Enquirer with its exclusive on Mr. Bezos’s affair. In an interview, Mr. Sanchez told me he did talk to the tabloid about his sister’s relationship (in an effort to help her), but denied sending it Mr. Bezos’s sexts, which he said he didn’t have access to. He theorized that The Enquirer had obtained the images via a Beverly Hills socialite who had gotten them directly from his sister.

I explained to two people with direct knowledge of The Enquirer’s reporting what Mr. Sanchez told me: that he’d provided some details of the affair to the tabloid, but not the sexts. These people, who would talk only about private conversations without attribution, emphasized that everything The Enquirer received on the Bezos affair, including the “below-the-belt selfie,” came from a single source.

These people added that the source was compensated by The Enquirer. How much? An amount well above the $150,000 that the tabloid paid the former Playboy model Karen McDougal to keep quiet about her alleged affair with Mr. Trump ahead of the 2016 election, they said.

Mr. Bezos changes Hollywood — and vice versa

For years, Mr. Bezos did not seem like the kind of chief executive who craved rock-star status. He didn’t employ a personal publicist to help bolster the Bezos myth, because he didn’t need to. The sheer reach of his company did the mythmaking for him: Amazon has transformed the way we read, shop and watch TV, and through its cloud services division runs an astonishingly large portion of the internet. Even as the company’s power grew, Mr. Bezos made a point of directing focus to the customer, who he said occupied “the empty chair” in every meeting.

Mr. Bezos bought a home in Beverly Hills in 2007, as Amazon was beginning to expand into entertainment. The company does not break out the financials of its Hollywood business, but it has been spending furiously to build a TV and film portfolio that enriches its Prime offering. Subscription services brought in more than $14 billion last year. To Hollywood insiders, the gusher of cash turned Mr. Bezos into the object of fascination and fear.

As Amazon bulldozed its way into the industry, Mr. Bezos transformed from a low-key, geeky Seattle dad to a chiseled presence on the red carpet. He has never seemed to be enthralled with the filmmaking process — he leaves day-to-day management to the Amazon Studios chief Jennifer Salke — but like Howard Hughes and other outsider tycoons before him, Mr. Bezos has unmistakably embraced the industry’s trappings.

His true Hollywood coming out was in 2016, when he gave a party — lavish even in the context of awards season — to celebrate the Oscar favorite “Manchester by the Sea,” an Amazon Studios production. Matt Damon was the co-host. It was held in a temporary edifice (only in Beverly Hills could it be called a “tent”) perched at the end of the long, pebbled driveway at Mr. Bezos’s mansion, high above Sunset Boulevard. The evening appears to be the first time that he and Ms. Sanchez were publicly photographed together.

They had met the previous year. As Amazon pushed into entertainment, it often worked with Endeavor, and Mr. Whitesell and Ms. Sanchez started socializing with the Bezoses. Their children played together at the Bezos family’s 29,000-square-foot compound outside Seattle, sprinting around a room decorated with NASA memorabilia and a chair in which J.K. Rowling wrote parts of the “Harry Potter” books. (It sold at auction for $394,000.)

Ms. Sanchez, an aviation enthusiast with a helicopter license, talked shop with Mr. Bezos, who spends much of his time building Blue Origin, his space exploration company. The two went flying together — encouraged by Mr. Whitesell, who saw the socializing as good for his wife’s aerial film and production company, Black Ops Aviation.

By last year, they were having an affair. Three people in Ms. Sanchez’s extended social circle said she was giddy and in love, showing amorous texts to a number of Brentwood and Beverly Hills moms.

‘Intensely focused’

At Amazon, Mr. Bezos has long implemented an idiosyncratic meeting structure. Executives sit in silence, reading a six-page memo on the topic at hand. Bullet points are frowned upon; the document must be a cogent narrative. Only once everyone has digested the “six-pager” do discussions begin.

That process may have been what Mr. Bezos was channeling when — without consulting Amazon brass — he published an explosive Medium essay on Feb. 7 accusing The Enquirer of extortion and blackmail. The tabloid was threatening to publish photos it had obtained, including one of Mr. Bezos’s “semi-erect manhood,” unless he met their conditions.

Mr. Bezos called out David Pecker, the chief executive of The Enquirer’s parent company, American Media, who has been known to wield his influence to benefit Mr. Trump. (Last year, federal prosecutors determined that American Media had made illegal payments to silence women who said they had had affairs with Mr. Trump.)

Mr. Bezos added that he had asked Mr. de Becker to conduct an investigation into how the tabloid had gotten his texts and photos. He implied that Mr. Trump and the Saudi royal family’s displeasure with The Washington Post, which he owns, were behind The Enquirer’s actions.

When Mr. Bezos published his essay, commentators were nearly unanimous in hailing it as a public relations masterstroke: Somehow, the world’s richest man, caught cheating on his wife, was now a victim.

But since then, more than three weeks have elapsed, and while Mr. de Becker has told The Washington Post that the Enquirer piece was “politically motivated,” direct proof of the Trump or Saudi links has not yet emerged. Asked repeatedly for such evidence, Mr. de Becker, who was traveling in Fiji, declined to comment on the record.

A person in Mr. Bezos’s camp, who was not authorized to speak on the record, said the investigation into the Enquirer story had moved beyond Mr. Sanchez, and to some extent was out of Mr. de Becker’s hands, now that evidence was with law enforcement.

Mr. Bezos and Ms. Sanchez remain together. On Feb. 19, Mr. Bezos spoke at the Yale Club in New York about his plan to populate the solar system with one trillion people through Blue Origin. “I try to organize my personal time so that I live mostly about two to three years out,” Mr. Bezos said, according to a transcript published on Business Insider. The New York Post elected to ignore the space-travel angle, reporting instead that he and Ms. Sanchez had been holed up in a Park Avenue “luxe love nest.”

So far, investors haven’t minded the messiness of Mr. Bezos’s personal life and his pull toward Hollywood. Amazon’s share price is up since the start of the year, and the company said that Mr. Bezos had not been distracted by the scandal. “Jeff remains as intensely focused on Amazon’s various businesses as ever, running daylong meetings of the S-Team (our leadership team) and daily forwarding emails he receives from customers to business leaders,” Mr. Carney wrote in an email.

Still, the incidents have left many adherents to the Bezos Way — who are legion — confused about what the events of the past several weeks say about Mr. Bezos’s judgment.

One former Amazon executive, who signed a nondisclosure agreement and could only discuss the company anonymously, wondered how Mr. Bezos’s behavior squared with a recent letter he sent to shareholders, in which he talked about irrevocable decisions, or what he called “one-way doors.”

“These decisions must be made methodically, carefully, slowly and with great deliberation and consultation,” Mr. Bezos said. “If you walk through and don’t like what you see on the other side, you can’t get back to where you were before.”