How Jeff Bezos' True Self Was Exposed by Donald Trump
Recently, Washington envisioned a scenario where Jeff Bezos would reign supreme in the Beltway. However, circumstances shifted.
TroibNews
It’s challenging to recall, but there was a period when excitement surrounded Jeff Bezos’ new mansion on S Street in Washington.
In 2016, shortly after purchasing The Washington Post, Bezos targeted a stunning 17,000-square-foot former museum crafted by the architect behind the Jefferson Memorial. After acquiring the property for $23 million in cash, he embarked on renovations intended for social gatherings, aiming to follow in the footsteps of a legendary Post figure.
“What he’s going to do is revive the legacy of Kay Graham and her great socializing — bringing smart, interesting people together in a social context,” Jean Case, a longtime friend of Bezos and his then-wife, remarked at the time.
This prediction was one that many in Washington's elite circles eagerly wanted to believe. The notion of a transformative capitalist hosting the political city’s social scene appealed to the establishment's ongoing desire for validation: "See, we’re not just a bunch of ill-dressed policy wonks!"
However, that validation never materialized. While Bezos did host a few events in his early days of ownership, his mansion often appeared desolate, with one Kalorama neighbor recalling a day when three cars were spotted in the driveway. “Almost all the time it’s dark,” noted Marie Drissel, another neighbor. “My guess is he’s there four or five nights a year.” In nearly a decade, she had only seen her famous neighbor once.
In Arlington, Virginia, similar sentiments linger. Amazon, under Bezos’ leadership, was expected to create up to 50,000 jobs with a new headquarters, which proponents claimed would dramatically alter the region. Virginia's win in the high-stakes competition for HQ2 delighted locals because it alleviated concerns that Washington was merely a government town.
However, eight years later and in the aftermath of a pandemic, Amazon employs around 8,000 people, making it the largest private employer in the county. Yet, the anticipated transformation hasn’t materialized, and the distinctive cylindrical headquarters building sits vacant, surrounded by unattractive fencing. Just last month, the Arlington County Board voted to use part of the Amazon site as a temporary location for an alternative high school. In a meeting set for June, they will consider granting the company another extension for starting work on the building.
“There’s some disappointment,” admitted Eric Cassel, president of the Crystal City Civic Association. “It’s a pretty cool building.”
In recent times, the absence of HQ2's architecture or Kalorama gatherings has become the least of Bezos’ worries from the perspective of Permanent Washington. His standing in Washington society has recently faced challenges. At the Post, he abruptly blocked a Kamala Harris endorsement and announced that the paper would only publish pro-market opinions—marking a shift in his public persona. His ideological leanings became apparent when he aligned himself with a group of business leaders at Donald Trump’s inauguration, creating an impression of self-interest rather than altruism. The individual who once praised democracy's safeguards has begun to resemble another wealthy figure attempting to gain favor with a transactional administration.
As a result, those who admired Bezos’ previous respectful and reverent public statements about journalism and democracy now express frustration over his perceived disrespect towards the venerable institution of The Washington Post and his apparent eagerness to ingratiate himself with the administration.
Reflecting on the initial excitement Washington had for Bezos underscores that the relationship spoke volumes about both the Beltway insiders and Bezos himself. This is especially relevant when engaging in the inevitable discussions about the fate of the gentleman owner of The Washington Post.
On the surface, the contrast between the Bezos of 2013-2023 and the Bezos of the last few years is quite remarkable.
The earlier Bezos embraced The Washington Post’s storied Watergate narrative, resisting political pressure on journalists during Trump's first term. He also established a $100 million award aimed at fostering civility—an aspirational ideal often cherished in Washington. Joining the Alfalfa Club, a traditional insider organization, was another nod to his acceptance within establishment circles. When he hosted a large dinner in celebration of a National Portrait Gallery exhibit in 2022, he filled the guest list with prominent figures such as Hillary Clinton, Anthony Fauci, and David Rubenstein. They were entertained in a home adorned with masterpieces and heavy drapery, evoking the decor of the White House's Green Room, according to one attendee.
Interestingly, this dinner coincided with the 30th anniversary party of Cafe Milano, a well-known gathering spot for political insiders. Many guests effortlessly transitioned from Bezos' dinner to the restaurant post-event.
Even after Joe Biden assumed the presidency and Bezos felt compelled to voice criticism regarding taxes, he did so through personal social media channels while leaving the newspaper's pages to professional journalists. “I would be humiliated to interfere. I would be so embarrassed. I would turn bright red,” he stated in a 2018 interview with Mathias Döpfner, CEO of Axel Springer, the parent company of PMG. “It would feel icky; it would feel gross.”
In contrast, the recent Bezos has overruled his editors to suppress a well-planned endorsement of Kamala Harris, abandoning the Post’s tradition of bipartisan opinions—a decision he personally announced rather than allowing it to unfold through the paper's standard processes. He joined other tech leaders in attending Trump's inauguration and is also financing a $40 million documentary about Melania Trump, a project discussed during a December dinner at Mar-a-Lago. This shift is stark for a man who once relished the gala premiere of *The Post*, a film depicting Katharine Graham's defiance against Nixon.
“People say it’s Invasion of the Body Snatchers,” remarked one Washington observer familiar with Bezos’ local engagements. “Something snapped with him.”
This notable change has instigated turmoil at The Washington Post, leading to a significant exodus of top talent and sharp criticism from former loyalists like Martin Baron, the former editor who depicted Bezos as stalwart amid serious financial pressures from Trump’s first administration. Baron has voiced concerns about Bezos exhibiting cowardice in the face of White House intimidation.
Beyond the confines of the Post, this shift has turned Bezos into a topic of speculation among Washington insiders: What transformed a figure who once revered Washington’s traditions into someone who appears eager to disregard them?
One theory suggests that Bezos’ divorce from civic-minded Mackenzie Scott and subsequent engagement to glamorous Lauren Sanchez influenced his disdain for the Washington style. In this interpretation, he regarded Washington’s elite as insignificant and chose to relocate to Miami.
Another theory posits that it was the Biden administration's corporate policies that pushed Bezos to join other tech moguls in distancing himself from the D.C. establishment. An additional narrative suggests that, like many wealthy media owners, he simply became weary of what he perceived as self-righteous, change-resistant journalism lifers, resulting in his rejection of the entire D.C. socio-political milieu.
I propose a different perspective: The essence of Bezos hasn’t changed; rather, the rules governing Washington have.
Individuals close to Bezos assert that he has never held a deep affinity for Washington. As a tech mogul, he shared the same “leave-me-alone” economic philosophy and disdain for bureaucratic proceduralism as younger leaders like Elon Musk—though he possessed superior social skills and a broader education, making him more presentable in Washington's circles.
Moreover, Bezos is exceedingly pragmatic—recognizing that while certain best practices are optional for a media mogul, they are crucial for a business leader in dealing with Washington.
These characteristics enabled Bezos to advocate for the news organization he acquired without disparaging it. He heaped praise on civic heroes like Katharine Graham, even buying a replica clothes-wringer for the newsroom to commemorate her bravery against Nixon-era threats. He visited legendary former editor Ben Bradlee, who was battling dementia. He bought the lock broken by the Watergate burglars, which had fetched $62,000 at auction.
While any owner might pay tribute to the rich history of a venerable institution, in Washington—especially as norms were being redefined under the first Trump administration—demonstrations of respect for tradition resonated strongly with an anxious political establishment. Particularly noteworthy was Bezos' respectful posturing, especially given that he arguably lost a multibillion-dollar Pentagon contract due to Trump's dissatisfaction with the Post’s coverage—including his formulation of the slogan “Democracy Dies in Darkness.”
Yet a less idealistic interpretation of his bravery exists: it was also a smart strategy.
At that time, prevailing sentiment suggested that Trump's presidency might be a temporary deviation and that the traditional institutional culture would reaffirm itself—and perhaps emerge even stronger. After all, HQ2 was taking shape near the Pentagon, which offered lucrative contracts for Bezos’ businesses. For a tycoon with diverse interests, being regarded in Washington as someone who honors tradition was a prudent approach. Such a culture functioned as a significant constraint on a mogul who might otherwise demand to have his way.
That dynamic has shifted, and Bezos may have recognized this change before the Washington establishment did.
Trump’s reelection last year highlighted a significant transformation in how to navigate the Beltway. The Biden administration's impact on the town’s culture and expectations proved negligible, even with Trump in exile to Florida. As it became evident in 2023 and 2024 that the allegedly disgraced 45th president could feasibly become the 47th, it underscored a change in the culture of Washington’s respectability coupled with a corresponding shift in media.
The old norms favored wealthy individuals who achieved influence through nonpartisan philanthropy, conventional media ownership, and substantial business investments like HQ2. The new paradigm is characterized by ideological media and overt displays of loyalty to those in power. For today’s elite placing their bets on D.C. interactions, the focus has shifted from bridging gaps as a bipartisan convenor to aligning closely with the administration.
These new principles are observable throughout the contemporary landscape. Nearby Bezos’ mansion, a fresh cohort of moguls, including Mark Zuckerberg and Peter Thiel, have purchased homes in D.C. As reported earlier this month, Zuckerberg matched Bezos in acquiring a $23 million residence, which high-end realtors indicated is part of a larger trend among oligarchs seeking Trump’s favor. The chatter surrounding these mansions no longer revolves around aspirations of bipartisan unity; their owners are not seeking to ingratiate themselves with the traditional political crowd. Similarly, media opportunities for high-profile interviews with administration officials and coveted briefing room seats increasingly flow to sharply partisan outlets, suggesting that upholding old-school integrity no longer serves as a means to enhance influence.
It’s no surprise that a practical individual like Jeff Bezos, with many diverse interests, would adapt to this new set of conventions.
“That’s the balance that has tipped. Trump 2.0 is different from the first term,” commented Cameron Barr, a former managing editor who recently severed ties with the Post due to Bezos’ announcement limiting editorial pieces to pro-market and pro-civil liberties. “The power balance is different. The mechanics of how to ‘work with Washington’ have changed.”
Barr is among veteran Post staffers advocating for Bezos to consider selling the newspaper. Yet he expresses concern that such a move wouldn't guarantee a favorable outcome for those wishing to see it thrive. “I think it’s possible to have a worse owner, even now, than Jeff Bezos, so I say that with some trepidation.”
This unease stems from the new norms in Washington, suggesting that many wealthy potential buyers would succumb to similar pressures that allowed Bezos to defy the old standards.
This brings us back to the early days of Bezos’ ownership and the thrilling anticipation that he might reshape the capital in ways we ultimately did not witness. In hindsight, it feels reminiscent of *The Music Man*; captivated by an idealized vision that catered to the capital’s insecurities, perhaps we were too enthusiastic to notice that he was merely playing by the rules. Even worse, many only recognized too late that those rules had fundamentally transformed.
Navid Kalantari for TROIB News
In 2016, shortly after purchasing The Washington Post, Bezos targeted a stunning 17,000-square-foot former museum crafted by the architect behind the Jefferson Memorial. After acquiring the property for $23 million in cash, he embarked on renovations intended for social gatherings, aiming to follow in the footsteps of a legendary Post figure.
“What he’s going to do is revive the legacy of Kay Graham and her great socializing — bringing smart, interesting people together in a social context,” Jean Case, a longtime friend of Bezos and his then-wife, remarked at the time.
This prediction was one that many in Washington's elite circles eagerly wanted to believe. The notion of a transformative capitalist hosting the political city’s social scene appealed to the establishment's ongoing desire for validation: "See, we’re not just a bunch of ill-dressed policy wonks!"
However, that validation never materialized. While Bezos did host a few events in his early days of ownership, his mansion often appeared desolate, with one Kalorama neighbor recalling a day when three cars were spotted in the driveway. “Almost all the time it’s dark,” noted Marie Drissel, another neighbor. “My guess is he’s there four or five nights a year.” In nearly a decade, she had only seen her famous neighbor once.
In Arlington, Virginia, similar sentiments linger. Amazon, under Bezos’ leadership, was expected to create up to 50,000 jobs with a new headquarters, which proponents claimed would dramatically alter the region. Virginia's win in the high-stakes competition for HQ2 delighted locals because it alleviated concerns that Washington was merely a government town.
However, eight years later and in the aftermath of a pandemic, Amazon employs around 8,000 people, making it the largest private employer in the county. Yet, the anticipated transformation hasn’t materialized, and the distinctive cylindrical headquarters building sits vacant, surrounded by unattractive fencing. Just last month, the Arlington County Board voted to use part of the Amazon site as a temporary location for an alternative high school. In a meeting set for June, they will consider granting the company another extension for starting work on the building.
“There’s some disappointment,” admitted Eric Cassel, president of the Crystal City Civic Association. “It’s a pretty cool building.”
In recent times, the absence of HQ2's architecture or Kalorama gatherings has become the least of Bezos’ worries from the perspective of Permanent Washington. His standing in Washington society has recently faced challenges. At the Post, he abruptly blocked a Kamala Harris endorsement and announced that the paper would only publish pro-market opinions—marking a shift in his public persona. His ideological leanings became apparent when he aligned himself with a group of business leaders at Donald Trump’s inauguration, creating an impression of self-interest rather than altruism. The individual who once praised democracy's safeguards has begun to resemble another wealthy figure attempting to gain favor with a transactional administration.
As a result, those who admired Bezos’ previous respectful and reverent public statements about journalism and democracy now express frustration over his perceived disrespect towards the venerable institution of The Washington Post and his apparent eagerness to ingratiate himself with the administration.
Reflecting on the initial excitement Washington had for Bezos underscores that the relationship spoke volumes about both the Beltway insiders and Bezos himself. This is especially relevant when engaging in the inevitable discussions about the fate of the gentleman owner of The Washington Post.
On the surface, the contrast between the Bezos of 2013-2023 and the Bezos of the last few years is quite remarkable.
The earlier Bezos embraced The Washington Post’s storied Watergate narrative, resisting political pressure on journalists during Trump's first term. He also established a $100 million award aimed at fostering civility—an aspirational ideal often cherished in Washington. Joining the Alfalfa Club, a traditional insider organization, was another nod to his acceptance within establishment circles. When he hosted a large dinner in celebration of a National Portrait Gallery exhibit in 2022, he filled the guest list with prominent figures such as Hillary Clinton, Anthony Fauci, and David Rubenstein. They were entertained in a home adorned with masterpieces and heavy drapery, evoking the decor of the White House's Green Room, according to one attendee.
Interestingly, this dinner coincided with the 30th anniversary party of Cafe Milano, a well-known gathering spot for political insiders. Many guests effortlessly transitioned from Bezos' dinner to the restaurant post-event.
Even after Joe Biden assumed the presidency and Bezos felt compelled to voice criticism regarding taxes, he did so through personal social media channels while leaving the newspaper's pages to professional journalists. “I would be humiliated to interfere. I would be so embarrassed. I would turn bright red,” he stated in a 2018 interview with Mathias Döpfner, CEO of Axel Springer, the parent company of PMG. “It would feel icky; it would feel gross.”
In contrast, the recent Bezos has overruled his editors to suppress a well-planned endorsement of Kamala Harris, abandoning the Post’s tradition of bipartisan opinions—a decision he personally announced rather than allowing it to unfold through the paper's standard processes. He joined other tech leaders in attending Trump's inauguration and is also financing a $40 million documentary about Melania Trump, a project discussed during a December dinner at Mar-a-Lago. This shift is stark for a man who once relished the gala premiere of *The Post*, a film depicting Katharine Graham's defiance against Nixon.
“People say it’s Invasion of the Body Snatchers,” remarked one Washington observer familiar with Bezos’ local engagements. “Something snapped with him.”
This notable change has instigated turmoil at The Washington Post, leading to a significant exodus of top talent and sharp criticism from former loyalists like Martin Baron, the former editor who depicted Bezos as stalwart amid serious financial pressures from Trump’s first administration. Baron has voiced concerns about Bezos exhibiting cowardice in the face of White House intimidation.
Beyond the confines of the Post, this shift has turned Bezos into a topic of speculation among Washington insiders: What transformed a figure who once revered Washington’s traditions into someone who appears eager to disregard them?
One theory suggests that Bezos’ divorce from civic-minded Mackenzie Scott and subsequent engagement to glamorous Lauren Sanchez influenced his disdain for the Washington style. In this interpretation, he regarded Washington’s elite as insignificant and chose to relocate to Miami.
Another theory posits that it was the Biden administration's corporate policies that pushed Bezos to join other tech moguls in distancing himself from the D.C. establishment. An additional narrative suggests that, like many wealthy media owners, he simply became weary of what he perceived as self-righteous, change-resistant journalism lifers, resulting in his rejection of the entire D.C. socio-political milieu.
I propose a different perspective: The essence of Bezos hasn’t changed; rather, the rules governing Washington have.
Individuals close to Bezos assert that he has never held a deep affinity for Washington. As a tech mogul, he shared the same “leave-me-alone” economic philosophy and disdain for bureaucratic proceduralism as younger leaders like Elon Musk—though he possessed superior social skills and a broader education, making him more presentable in Washington's circles.
Moreover, Bezos is exceedingly pragmatic—recognizing that while certain best practices are optional for a media mogul, they are crucial for a business leader in dealing with Washington.
These characteristics enabled Bezos to advocate for the news organization he acquired without disparaging it. He heaped praise on civic heroes like Katharine Graham, even buying a replica clothes-wringer for the newsroom to commemorate her bravery against Nixon-era threats. He visited legendary former editor Ben Bradlee, who was battling dementia. He bought the lock broken by the Watergate burglars, which had fetched $62,000 at auction.
While any owner might pay tribute to the rich history of a venerable institution, in Washington—especially as norms were being redefined under the first Trump administration—demonstrations of respect for tradition resonated strongly with an anxious political establishment. Particularly noteworthy was Bezos' respectful posturing, especially given that he arguably lost a multibillion-dollar Pentagon contract due to Trump's dissatisfaction with the Post’s coverage—including his formulation of the slogan “Democracy Dies in Darkness.”
Yet a less idealistic interpretation of his bravery exists: it was also a smart strategy.
At that time, prevailing sentiment suggested that Trump's presidency might be a temporary deviation and that the traditional institutional culture would reaffirm itself—and perhaps emerge even stronger. After all, HQ2 was taking shape near the Pentagon, which offered lucrative contracts for Bezos’ businesses. For a tycoon with diverse interests, being regarded in Washington as someone who honors tradition was a prudent approach. Such a culture functioned as a significant constraint on a mogul who might otherwise demand to have his way.
That dynamic has shifted, and Bezos may have recognized this change before the Washington establishment did.
Trump’s reelection last year highlighted a significant transformation in how to navigate the Beltway. The Biden administration's impact on the town’s culture and expectations proved negligible, even with Trump in exile to Florida. As it became evident in 2023 and 2024 that the allegedly disgraced 45th president could feasibly become the 47th, it underscored a change in the culture of Washington’s respectability coupled with a corresponding shift in media.
The old norms favored wealthy individuals who achieved influence through nonpartisan philanthropy, conventional media ownership, and substantial business investments like HQ2. The new paradigm is characterized by ideological media and overt displays of loyalty to those in power. For today’s elite placing their bets on D.C. interactions, the focus has shifted from bridging gaps as a bipartisan convenor to aligning closely with the administration.
These new principles are observable throughout the contemporary landscape. Nearby Bezos’ mansion, a fresh cohort of moguls, including Mark Zuckerberg and Peter Thiel, have purchased homes in D.C. As reported earlier this month, Zuckerberg matched Bezos in acquiring a $23 million residence, which high-end realtors indicated is part of a larger trend among oligarchs seeking Trump’s favor. The chatter surrounding these mansions no longer revolves around aspirations of bipartisan unity; their owners are not seeking to ingratiate themselves with the traditional political crowd. Similarly, media opportunities for high-profile interviews with administration officials and coveted briefing room seats increasingly flow to sharply partisan outlets, suggesting that upholding old-school integrity no longer serves as a means to enhance influence.
It’s no surprise that a practical individual like Jeff Bezos, with many diverse interests, would adapt to this new set of conventions.
“That’s the balance that has tipped. Trump 2.0 is different from the first term,” commented Cameron Barr, a former managing editor who recently severed ties with the Post due to Bezos’ announcement limiting editorial pieces to pro-market and pro-civil liberties. “The power balance is different. The mechanics of how to ‘work with Washington’ have changed.”
Barr is among veteran Post staffers advocating for Bezos to consider selling the newspaper. Yet he expresses concern that such a move wouldn't guarantee a favorable outcome for those wishing to see it thrive. “I think it’s possible to have a worse owner, even now, than Jeff Bezos, so I say that with some trepidation.”
This unease stems from the new norms in Washington, suggesting that many wealthy potential buyers would succumb to similar pressures that allowed Bezos to defy the old standards.
This brings us back to the early days of Bezos’ ownership and the thrilling anticipation that he might reshape the capital in ways we ultimately did not witness. In hindsight, it feels reminiscent of *The Music Man*; captivated by an idealized vision that catered to the capital’s insecurities, perhaps we were too enthusiastic to notice that he was merely playing by the rules. Even worse, many only recognized too late that those rules had fundamentally transformed.
Navid Kalantari for TROIB News
