At 5:30 a.m., a line is already forming outside one of the most exclusive addresses in America. Old pickup trucks and compact cars wait in the palm-lined driveway, windows down, cards ready. A quick glance at security and the gate opens - gardeners, housekeepers and dog walkers cross a Venetian-like bridge and enter the private island of Indian Creek.
There is almost no traffic in the opposite direction, except for the occasional convoy of black SUVs driving billionaires towards Miami Beach, Florida.
There are only 40 villas on the island, worth about $100 million. Among the 80 or so residents are Tom Brady, David Guetta, Mark Zuckerberg, Jared Kushner. And Jeff Bezos.
With a fortune of $225 billion, Bezos “plays in a different league even on Indian Creek,” says Dina Goldenteyer, who has managed his real estate business on the island for years. The world’s fourth-richest man owns three villas on Biscayne Bay there, two of which are next to each other. He is currently demolishing them to build a “mega mansion” in their place. Until then, he is living in a third house, nearby, because one has to sleep somewhere, Goldenteyer adds.
Indian Creek is a separate municipality, with a mayor, a prosecutor, and a police force that quickly turns away curious visitors. As pompous as Donald Trump imagines America to be, but also uglier as it becomes.
It's hard to imagine a greater degree of seclusion. That's what, Goldentheyer says at a meeting in Miami Beach, makes the island perfect: "Complete exclusivity. That's what people like Bezos are looking for." And he can afford it.
In less than 30 years, the 62-year-old Amazon founder has built an empire. His company sold about 250 products per second last year. Space firm Blue Origin has taken nearly 100 tourists into space since 2021, while AWS powers factories, trains and websites around the world.
Bezos has robotaxis in San Francisco and satellites in low Earth orbit. He is currently trying to raise $100 billion to digitize heavy industry through AI startup Prometheus. Since 2013, he has also owned the famous “Washington Post”.
He's a legend. And he was long considered boring. The headlines were filled with criticism of the unfavorable working conditions at Amazon, not his personal image.
Little is known about Bezos's outbursts. The eldest of three children, he was raised by a single mother for a long time. He was not a "rich kid," without an overblown ego and a need for attention. A numbers man. Ruthlessly rational. With an unerring business instinct and a clear political compass. For years, a Democrat and critic of Donald Trump - who once called him "Jeff Bozo." At the time, Bezos retorted that such a president should be sent into space - "I would reserve him a seat on a Blue Origin rocket."
That was the Bezos the world knew. The one the startup scene admired and emulated. Knew. Admired. Emulated. Past tense. History.
Since Trump's return to power, Bezos has acted like a different person - in the role of a vulgar playboy. He has become one of his closest allies, a kind of alter ego - as rich as Elon Musk, but unlike him, he looks better in a tuxedo and is more predictable.
Bezos has been in a relationship with TV personality Lauren Sanchez since 2019, following his divorce from writer Mackenzie Scott. Last year, they held a lavish wedding in Venice with more than 200 guests arriving on 90 private jets - including Kim Kardashian, Queen Rania of Jordan and Ivanka Trump. His new company and extravagances that the old Bezos would hardly have allowed himself.
Instead of boring Seattle, he now lives in Indian Creek. He throws parties on a yacht, shows off his sculpted body, and appears at the Oscars with a gray beard - like he's in a commercial for a flashy men's perfume. It's not just his image that has changed.
Bezos congratulated the president on his “remarkable political comeback” and praised his “great composure and courage under literal fire.” He is now a regular at Trump’s MAGA rallies and was in close proximity to the president at the inauguration. Amazon also donated millions to the inaugural ball and the new White House ballroom.
Shortly after the lunch at Trump's Mar-a-Lago, Bezos' MGM paid the president's family nearly $30 million for a documentary about Melania. His company also acquired the rights to "The Apprentice," the reality show that made Trump famous, with a good portion of the proceeds going directly to the president.
Trump is happy to exploit new alliances: when Amazon considered including its share of tariffs in its prices last spring, all it took was one call from the White House to Bezos and the idea was immediately rejected.
To Trump's delight and the horror of liberal America, Bezos is dismantling his most valuable political asset - The Washington Post. He has taken control of the editorial policy of the once Democratic-leaning paper and steered it towards the MAGA line: the comments section will henceforth defend "personal freedoms and the free market."
And with a drastically reduced editorial staff. He fired a third of journalists and shut down the sports and most foreign bureaus - supposedly for the sake of modernization and efficiency. Or to please Trump?
The president welcomes the turnaround and says Bezos is “very nice,” “great,” and a “good man.”
His former admirers are now more skeptical. “Now they call him a doormat, a coward, an opportunist. And I understand that,” says a person who has been close to him for years. His behavior, he adds, seems spineless and unprincipled. Others argue that he is actually opposed to Trump and is only trying to mitigate the damage - which would, paradoxically, bring him even closer to the “clown” that Trump has always seen him as.
To Trump's delight and the dismay of liberal America, Bezos is dismantling his most valuable political asset - The Washington Post. He has taken control of the editorial policy of the once Democratic-leaning paper and steered it toward the MAGA line.
Between these two poles lies perhaps the most extraordinary transformation of an American tech billionaire. Even close friends have difficulty reconciling the “two Bezos” – before and after the fall of 2024. “It’s like they’re two completely different personalities,” says one of them. He seems, he adds, to be going through a “serious midlife crisis.”
Is that the whole explanation?
Bezos often talks about his grandfather, Lawrence Giesi, whose Texas ranch he spent almost every summer from the ages of four to sixteen. There he learned to fix windmills, vaccinate cattle, and do other chores—a life of independence in which he had to solve problems on his own. He later called the experience crucial to his development. As a boy, on a trip with his grandparents, he calculated how much smoking shortens her life and told her she had “lost” nine years. Instead of being proud of his insight, his grandmother burst into tears. His grandfather stopped the car, took him outside, and calmly said to him:
"Jeff, one day you'll realize that it's harder to be good than smart."
That sentence became one of his life's guiding principles. Intelligence is a gift, he would later say, but goodness is a choice. His true test of character came much later - and he failed.
His career progressed rapidly. After studying at the elite Princeton University, he rejected Silicon Valley and chose the safer path - Wall Street. At the age of 30, he became a vice president at the hedge fund DE Shaw, which used mathematical models to find and exploit market anomalies.
He and his wife, Mackenzie Scott, stayed in New York for eight years, only to stumble upon his own business “anomaly” in the mid-1990s: the mathematical genius realized that the number of Internet users was growing 100 percent annually. He concluded that books were an ideal product for online sales – there were about three million of them, while even the largest bookstores only offered a fraction of that. The difference, he realized, was the business opportunity: a “universal offering,” selling “every book in the world.”
When he told his wife that he wanted to leave his secure job and move across the country to start an online bookstore, she supported him, although, as Bezos recounts, she first asked: “What is the Internet?”
Bezos believed in the idea, but not in Silicon Valley, where dot-com entrepreneurs of the time were more interested in partying than in business. In Seattle, he estimated, labor and warehouses were cheaper.
The couple lived a secluded life, far from glamour. They had four children, and this lifestyle, as Scott later said, more reflected her character: “Jeff is my opposite - he is sociable and loves people.”
In 2013, Bezos received a call from investment bank Allen & Co. The Grahams, one of the oldest publishing families in the United States, were considering selling The Washington Post. At the time, Bezos had no idea how a newspaper was run, nor did he plan to buy it—especially not such an institution of American democracy. Yet, just a few weeks after meeting Don Graham at a conference in Sun Valley, known as “summer camp for billionaires,” the deal was done: Bezos paid $250 million for The Post.
For the billionaire, the sum was insignificant, as his yacht cost twice as much. According to Graham, Bezos didn't even negotiate: "I just named the price, and Jeff agreed."
From today's perspective, the purchase seems like a step from the shadows to the top of society. In 2016, he bought one of the most expensive properties in Washington for $ 23 million - a building designed by the architect of the famous Jefferson Memorial. He invested another $ 12 million in renovating the 11-bedroom mansion and furnishing it with art. The Bezos family, however, hardly ever stayed there, neighbors told reporters.
The purpose of the residence was different: Barack Obama and Ivanka Trump became his neighbors. Distinguished guests were happy to drop by, and the billionaire began throwing parties that Katharine Graham was once known for. Bezos respected the legendary publisher of the Post and wanted, as his longtime friend Jean Case puts it, to “revive her legacy and social life.”
Did he want to become someone else? And was he even able to?
Bezos met his future wife, Lauren Sanchez, at a movie premiere in 2016. A political shock soon followed: Donald Trump, an outspoken opponent of the media who had increasingly attacked the Washington Post, was elected president. Bezos then faced serious pressure in the publishing business for the first time. In 2019, Amazon lost an almost certain $10 billion government contract for the JEDI project, which went to Microsoft. Trump spent months attacking Bezos, ridiculing him and criticizing the Post, and then stepped up the pressure - accusing him of tax evasion and threatening to drastically increase the price of Amazon's postal services.
Trump wanted the billionaire to feel his wrath on his business results.
Bezos was deeply shaken, his friends said at the time. He felt he was being treated unfairly and saw himself as a victim of Trump, whom he saw as a tyrant who was undermining American democracy. Eventually, he fought back: Amazon sued the Pentagon and even Trump himself, accusing him of “unlawful interference” in the JEDI contract.
In the Post, he took a firm stance - Trump should be resolutely opposed. "Stewardship of the Post and support for its mission, which will remain unwavering, will be something I will be most proud of when I am 90 and look back on my life," he wrote.
The editorial staff joked that the Post cost Bezos not just $250 million, but $10 billion plus $250 million. “That was extraordinary,” says then-editor-in-chief Martin Baron of Bezos’s support for the paper. He ran the paper under his ownership for eight years. “Every government must have oversight,” was one of Bezos’ favorite messages at editorial meetings—and during Trump’s first term, he showed how seriously he took it. Baron says he respected him for that: How many owners would be willing to defend such a media outlet if they were risking a $10 billion contract?
Brave, steadfast, combative - despite the pressures and the huge financial consequences for his companies. That's how Bezos is remembered by Baron: as an unwavering fighter for what he believes is right.
Before joining the Post in 2012, Baron was editor-in-chief of the Boston Globe and the Miami Herald. Wherever he worked, investigative journalism was gaining momentum - readers kept coming back, new ones were coming. Most notably at the Post: with Bezos's investment, the editorial office was digitized, expanded, and reporting from the White House was intensified. More than 1.000 journalists wrote for the paper, which had over three million digital subscribers. The "Trump effect" played a key role - the constant scandals from the White House provided a constant flow of new stories.
While the Post’s main rival, the New York Times, began preparing for the end of Trump’s chaotic tenure in the early 2020s, expanding its business model through recipes, games, and acquisitions like the Wirecutter platform, Bezos, as Baron says, “didn’t pay attention.” Baron claims that he was repeatedly invited to come to Washington and define a strategy for the post-Trump period. Bezos, however, did not come - nor did he give any guidance. He was only told to monitor potential acquisitions, but, as he says, he was too overwhelmed with the day-to-day running of the editorial office to deal with that any further.
Bezos also radically changed his life during this period. He divorced his longtime wife in 2019, and the very next day his relationship with Fox News journalist Lauren Sanchez, a person who enjoys the public eye, became public.
Amazon acquired the MGM film studio in 2021, and Bezos soon stepped down as CEO and moved to the supervisory board.
As Trump left the White House and America entered a calmer political rhythm, Bezos began a new life - between a yacht and a private plane, between Hollywood and Miami Beach.
Suddenly, all his political fighting spirit was gone. Bezos seemed to have lost interest in journalism. After Barron’s departure in 2021, he focused on other projects — most notably Blue Origin and artificial intelligence. The Post began to falter, losing readers and award-winning journalists, changing editors, and once again losing money — nearly $100 million by 2024, the year Trump returned.
That same year, Bezos began to consider breaking with its long tradition of supporting presidential candidates. In late October 2024, 11 days before the election, the newspaper officially announced, at his behest, that it would not endorse any candidate.
Addressing readers in the Post, Bezos wrote: “You can see my wealth and business interests as a hedge against intimidation, but also as a web of conflicting interests. Only my principles can weigh one way or the other.”
Just hours earlier, the head of his space company Blue Origin, David Limp, met with Trump, who planned to pour billions into NASA to return to the Moon and go to Mars. Bezos has claimed that the two events are unrelated, but at least $3,5 billion from that program ended up in his companies.
Bezos re-engaged in the Post in early 2025, steering it in a more pro-Trump direction. Personal freedoms and free markets were prioritized, rather than the paper’s earlier role of holding the powerful accountable. This was seen as a capitulation by the editorial staff. “In our experience since the 1960s, morale at the Post has never been lower,” former editors Leonard Downey Jr. and Robert Kaiser wrote in an email to Bezos.
The motto “Democracy Dies in the Dark,” which Bezos himself once chose, sounds different today. Baron believes that Bezos is dealing a “death blow” to the newspaper. In early 2026, more than 300 editors were fired - “one of the darkest days in the history of the media,” Baron said, accusing the owner of destroying the reputation and position of the “Post”.
The paper has lost half a million readers in recent years, as well as many of its best journalists. Such damage, Baron believes, is not easy to repair. The relationship between reader and newspaper is not a mere transaction - but one of trust and loyalty. "It's like a marriage," he says. And Bezos, he adds, "has filed for divorce - and an ugly divorce."
Is Bezos afraid of Trump's retaliation? Or is it about business - a safer path for Amazon, government contracts for Blue Origin, and lighter regulation for his AI projects?
The paradox is that, despite his efforts to get closer to Trump, Bezos cannot feel safe - the president still holds all the strings. The investigation into Amazon's alleged monopoly has not been suspended, on the contrary, hearings are set to begin in October. His core business faces possible disruption, while Blue Origin's contracts with NASA are not permanent either.
Bezos, however, insists he remains committed to the Post and that selling is not an option. The cuts, he says, are part of an attempt to stabilize the company, and the layoffs and editorial decisions have nothing to do with his other business interests.
Baron, a former editor-in-chief, doesn't believe in conspiracy theories - he sees it more as an attempt to repair the damage. Bezos can handle losses, he says, but he doesn't want to lose $100 million or more for years. That's why the business is being radically reduced. According to him, Bezos believes that the old model no longer works and that everything needs to be torn down and started over.
When? Maybe after Trump. If anything remains by then - of the newspaper. And of Bezos' credibility.
The paradox is that, despite his efforts to get closer to Trump, Bezos cannot feel secure - the president still holds all the strings.
Baron sees a way out - a foundation with a billion dollars, enough to finance the Post for the next ten years. An independent board of directors would maintain political neutrality, and then the paper would have to stand on its own two feet. That, he says, would guarantee full independence, while Bezos could also take advantage of tax breaks.
Hollywood's end - maybe too good to be true.
As things stand now, the questions Bezos posed to Princeton graduates in 2010 still hang over him today:
"Will you bow to criticism or follow your convictions?"
“Will you excuse yourself when you are wrong or will you apologize?”
“Will you protect your heart from rejection or will you act when you fall in love?”
Bezos ended the speech with a powerful message: "When you are 80 years old and quietly look back on your life, the most important story will be the one about the choices you made."
Baron says he feels "betrayed" - as if his life's work and part of American history have been taken away.
It's possible that this is the story that Jeff Bezos will eventually leave behind.
Prepared by: A. Š.
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