John Oliver's Bold Remarks: Criticizing Jeff Bezos’ Cozy Relationship with Donald Trump

In an episode of Last Week Tonight, John Oliver unleashed a scathing attack on Amazon billionaire Jeff Bezos, criticizing his ever-growing connection with former President Donald Trump.

The late-night host didn’t hold back, making a particularly saucy NSFW joke to emphasize his point about the shift in Bezos’s relationship with Trump over the past year.

Oliver devoted his entire Sunday night monologue to defending the press against Trump’s relentless attacks. As the audience waited for the usual political banter, it didn’t take long for Oliver to target one of Trump’s business allies—Bezos.

The long-standing relationship between Trump and Bezos has been under scrutiny ever since Trump’s first term. Notably, Bezos owned The Washington Post, a paper famous for its front-page slogan, “Democracy Dies in Darkness.” This slogan, once synonymous with fearless investigative journalism, is now absent, and so too is the paper’s previous aggression in its coverage of Trump.

Oliver’s observation was sharp: “Even before the election, they seemed noticeably gentler.” He continued to explain how Bezos’s ownership seemed to affect the paper’s editorial stance.

He highlighted the time when Bezos allegedly pushed for The Post to abandon its endorsement of former Vice President Kamala Harris during the 2020 election.

Oliver also mentioned the shift in the paper’s editorial direction in early 2025 when Bezos demanded that the op-ed pages only discuss topics like “personal liberties and free markets,” a move that many critics saw as aligning the paper more with conservative principles rather than its usual independent stance.

But it didn’t stop there. Oliver wasn’t just throwing jabs at the paper’s editorial direction. He also turned his attention to Bezos’s involvement in Trump’s circle, specifically referencing the documentary that Amazon paid a whopping $40 million to license.

The documentary, which focused on Trump’s wife Melania, was the most expensive project of its kind for Amazon. Oliver couldn’t resist pointing out the sheer absurdity of Bezos’s actions, particularly when it seemed like the billionaire was going out of his way to make nice with Trump and his administration.

“C’mon!” Oliver exclaimed, “That’s not just bending the knee. That’s bending both knees, arching your back, and relaxing your holes.”

As the audience erupted in laughter, Oliver’s bold humor cut through the tension surrounding Bezos’s public image. Oliver’s NSFW joke was more than just a punchline—it was a sharp critique of how Bezos, a man known for his tech empire and reputation as a progressive force in the business world, appeared to be getting too cozy with the president who had once been his adversary.

Oliver’s criticism was more than just comedic; it served as a commentary on the state of the media and corporate alliances in the modern era. Bezos, once the fierce competitor and visionary who built Amazon from the ground up, now found himself in bed with the very people he had publicly criticized in the past.

The stakes of this criticism became even more pronounced when Oliver pointed out that Bezos wasn’t the only media mogul making such concessions. He also cited Patrick Soon-Shiong, the billionaire owner of the Los Angeles Times, who reportedly asked his staff to “take a break” from writing about Trump.

This call for a media pause came just as Trump’s re-election campaign gained traction, raising questions about the pressures placed on media outlets owned by the ultra-wealthy.

But back to Bezos. The heart of Oliver’s argument wasn’t just about Bezos’s apparent political shift; it was about the larger implications of this shift in the context of America’s media landscape. Bezos, as the owner of one of the world’s most powerful media outlets, had the ability to influence the public narrative.

When he chose to support Trump, either through financial investments or through editorial changes at The Post, it was clear that Bezos had crossed a line. It wasn’t just about business anymore; it was about aligning himself with power in a way that many saw as compromising his principles.

In fact, Oliver’s dissection of Bezos’s actions went deeper than just his business dealings. The billionaire’s connections to Trump, Oliver argued, symbolized a larger trend of tech moguls and media magnates bending to the will of political power, all while maintaining an image of moral superiority.

Bezos’s supposed moral high ground—embodied in his previous advocacy for issues like climate change and worker’s rights—seemed to crumble when he began to backtrack on those very principles in exchange for political favor.

To some, this wasn’t just a case of Bezos playing both sides of the political aisle. It was evidence of the power structure in America becoming more entrenched in the hands of the ultra-wealthy.

In the eyes of many, Bezos’s behavior was an example of the elite class choosing to protect their interests at the expense of the broader public. His cozy relationship with Trump seemed less like a mere political alliance and more like a deliberate move to secure his position at the top of the corporate ladder.

As Oliver delved into the murky world of corporate politics, his sharp words rang true: the lines between business and politics were increasingly becoming indistinguishable.

The tech world, once a beacon of innovation and disruption, now appeared to be mirroring the same power dynamics that have long dominated traditional industries like oil and finance.

For many watching, it was a sad reality—one where billionaires like Bezos, once seen as disruptors of the status quo, were now working to preserve the very systems they had once claimed to challenge.

Oliver’s words served as both entertainment and a wake-up call. The once untouchable Bezos, who had built Amazon into one of the most powerful companies in the world, was now being held to account for his actions.

The world was beginning to see a new side of Bezos—a side that some found disappointing, even hypocritical.

For Oliver, the billionaire’s cozying up to Trump wasn’t just a matter of personal politics; it was a reflection of the larger issue at play: the way in which wealth, power, and influence were being used to shape the narrative of the country.

But as Oliver joked, “The real question is: how many knees will Bezos bend before he becomes the most powerful man in the world’s most uncomfortable position?” It was a pointed and hilarious jab, but it underscored a deeper truth: when the line between media, business, and politics becomes blurred, the public trust is the first casualty.

In the end, John Oliver’s relentless criticism of Bezos served as a reminder that even the most powerful figures in society are not immune to scrutiny.

The jokes, while laugh-out-loud funny, carried with them a message that resonated beyond the studio audience: in a world where billionaires hold the reins of power, the public must remain vigilant and never allow the line between corporate interest and political influence to disappear entirely.