Jeff Bezos Called Washington Post His Worst Investment and Staff He Laid Off "Terrible" People
The Dinner That Changed Everything
It's December 2024. The world's third-richest man sits down for dinner with the incoming President of the United States. The conversation turns to business. And then, Jeff Bezos, the guy who built Amazon from a garage startup into a trillion-dollar empire, makes a stunning confession.
Buying The Washington Post, he says, was his worst investment ever.
Not Pets.com, where he lost $50 million. Not LivingSocial, where Amazon sank $175 million only to watch it collapse. The Washington Post. The newspaper he bought in 2013 for $250 million, the one that broke Watergate, the one that was supposed to be his legacy in journalism.
According to a soon-to-be-released book by New York Times journalists Jonathan Swan and Maggie Haberman, Bezos didn't stop there. He complained that the Post's staff were "terrible." That they "don't listen." That unlike his other companies, the people at the Post simply wouldn't follow his lead.
Two months later, he laid off more than 300 of them.
This is the story of how a billionaire's dream investment turned into a $100 million nightmare, and what happens when the world's richest man decides he's done playing nice.
What Exactly Did Bezos Say to Trump?
Let's start with the words themselves. Because if you're going to call something your worst investment ever, you'd better have a good reason.
"The People There Are Terrible"
According to excerpts from Regime Change: Inside the Imperial Presidency of Donald Trump, which hits shelves June 23, Bezos didn't mince words at that December 2024 dinner.
"The people there are terrible," he reportedly told Trump. "They don't listen. My other companies, they listen."
Think about that for a second. This is a guy who runs Amazon, Blue Origin, and a dozen other ventures. He's used to people doing what he says. But at the Post? Apparently, not so much.
The "Lost Friends" Clarification
Here's where it gets even more interesting. According to Swan and Haberman, Trump later claimed that Bezos told him he'd lost half his friends over the Washington Post investment.
Bezos reportedly pushed back on that characterization. He hadn't lost friends, he said, but people close to him had urged him to sell the newspaper.
Either way, the message is clear: owning the Post has been a social and financial headache for the billionaire.
Why Was Bezos So Frustrated?
The answer goes back to October 2024, just weeks before the dinner. The Post's editorial board had drafted an endorsement of Kamala Harris for president. Bezos personally intervened to kill it.
The backlash was immediate and brutal. More than 250,000 subscribers canceled their subscriptions, about 10% of the paper's digital base.
Bezos defended the decision by arguing that presidential endorsements don't tip elections anyway. But inside the newsroom, it felt like a betrayal. Several senior staff resigned on the spot.
By the time Bezos sat down with Trump, he was already nursing wounds from that firestorm. And he wasn't shy about sharing his frustrations.
The Timeline: From Dinner to Mass Layoffs
Let's trace the sequence of events. Because when you connect the dots, a clear, and troubling, picture emerges.
October 2024 – Killing the Harris Endorsement
- Post editorial board drafts Harris endorsement
- Bezos personally blocks publication
- 250,000+ subscribers cancel
- Multiple senior staff resign
- The Post ends its tradition of presidential endorsements entirely
December 2024 – The Trump Dinner
- Bezos and Trump dine together
- Bezos calls the Post his worst investment
- Complains staff are "terrible" and "don't listen"
- Trump tells Bezos: "This Washington Post is really unfair. You've got to take better care."
January 2025 – First Round of Cuts
- Post eliminates 4% of staff, mostly in advertising
- Focus on the business side
February 2025 – The Mass Layoffs
- More than 300 employees laid off, roughly one-third of the workforce
- Entire sports department eliminated
- All staff photographers let go
- Foreign coverage drastically reduced
- Local/metro coverage gutted
February 2025 – Bezos Announces Opinion Section Overhaul
- Post's opinion pages will now focus exclusively on "personal liberties and free markets"
- Viewpoints opposing those pillars will not be published
The Damage Done
One employee called the situation "an absolute bloodbath." The New York Times described it as "an extremely grim outcome" and "a dark day" for the paper.
And Bezos? He stayed silent.
Why Bezos Called It His Worst Investment
Here's the thing about Jeff Bezos: the guy knows how to make money. Amazon, Whole Foods, Audible, Twitch, the list of winning bets is long. So when he calls something his worst investment, it's worth paying attention.
The Financial Numbers Don't Lie
Let's look at the math:
- 2023: The Post lost $77 million
- 2024: The Post lost roughly $100 million
- 2025: The Post lost more than $100 million, some sources say up to $125 million
That's nearly $300 million in losses over three years.
As one source told The Wall Street Journal, the Post's expenses had outpaced revenues every year between 2022 and 2025, while story counts had fallen by 42% since 2020.
Bezos, speaking at a 2024 summit, had said he was providing resources to the Post, but his patience had worn thin.
The Subscriber Revolt
The 250,000 subscribers who canceled after the Harris endorsement non-decision didn't just cost the Post revenue, they sent a message.
Readers weren't just upset about the endorsement itself. They saw it as Bezos kowtowing to Trump, a man who had spent years attacking the media.
Former Post executive editor Martin Baron called Bezos's decision a "gutless order" that made the paper's problems "infinitely worse."
A Pattern of Failed Bets
Believe it or not, the Washington Post isn't Bezos's first investing stumble. Remember Pets.com? Bezos once compared losing his $50 million stake to "getting a root canal with no anesthesia."
Then there was LivingSocial, the daily deals site Amazon sank $175 million into, only to see it bought for $0 six years later.
Even Blue Origin, his space company, has had its share of spectacular failures.
But the Post is different. It's not just about the money. It's about legacy, influence, and a 150-year-old institution that was supposed to be his gift to journalism.
Instead, it's become a $100 million black hole.
The Human Cost – What the Layoffs Actually Meant
Let's pause for a moment and talk about the people behind the numbers. Because when Bezos called the Post staff "terrible," he wasn't just talking about abstract employees. He was talking about real journalists doing real work.
One-Third of the Workforce Gone
When the layoffs hit in February 2025, they eliminated roughly one-third of the Post's staff, about 300 of the paper's 800 journalists.
Not 4%. Not 10%. One-third.
What Was Cut
The scope of the cuts was devastating:
- Sports department – eliminated entirely
- All staff photographers – let go
- Most of the video team – dismissed
- Foreign coverage – drastically reduced
- Metro/local coverage – sharply cut back
- Books section – eliminated
- Tech, science, and business teams – hit hard
The Reaction
Observers called the cuts "devastating." One employee described the scene as "an absolute bloodbath."
Long-time colleagues were informed of their departures as the newsroom watched in shock.
Columbia University journalism professor Margaret Sullivan called it "sad news for anyone interested in American and world journalism."
And where was Bezos while all this was happening? At the Super Bowl, according to reports, while his publisher Will Lewis was also spotted partying in San Francisco.
The optics couldn't have been worse.
What This Says About Billionaire-Owned Media
This isn't just a story about one billionaire and one newspaper. It's a story about what happens when the ultra-wealthy buy media companies, and what happens when they lose interest.
The Promise vs. The Reality
When Bezos bought the Post in 2013, it felt like a new chapter for journalism. A tech visionary with deep pockets, committed to saving a storied institution.
He told staff at the time that "making money isn't enough. It also has to be growing." Continuing to cut staff, he said, would lead to "extinction, or at best, irrelevance."
Fast forward a decade, and here we are.
When Owners and Newsrooms Clash
The tension between Bezos and the Post's newsroom isn't new. In 2024, he admitted he was "a terrible owner for The Post from the point of view of appearance of conflict."
But the conflict runs deeper than appearances. Bezos wanted a newsroom that listened. The newsroom wanted an owner who didn't interfere.
And when Bezos killed that Harris endorsement, he shattered whatever trust remained.
The Future of The Washington Post
So where does the Post go from here?
Bezos has denied reports that he's looking to sell. But the paper is now a shell of what it once was. No sports section. No staff photographers. Barely any foreign coverage. A newsroom that's lost a third of its people.
One former Post fact-checker told Bezos to either commit to saving the paper or sell it to someone who will.
For now, the Post is trying to reinvent itself. New content and licensing deals with OpenAI, Apple News+, and Alexa+ are bringing in revenue. A new acting publisher, Jeff D'Onofrio, has said he's "going to fight like hell for this institution."
But the question remains: can a newspaper that's been gutted of its best talent and its owner's trust ever recover?
A Cautionary Tale
Jeff Bezos called the Washington Post his worst investment. He told the President of the United States that the staff were "terrible" and "don't listen." Two months later, he laid off more than 300 of them.
This is a story about money, yes, $100 million losses, $250 million purchase prices, and the math that doesn't add up.
But it's also a story about something deeper. It's about what happens when a billionaire buys an institution and discovers he can't control it. It's about the tension between ownership and journalism, between profits and purpose, between what a CEO wants and what a newsroom needs.
And it's a warning: even the world's richest man can't buy his way into making a newspaper do what he wants.
Whether the Washington Post survives this chapter, and whether Bezos ever finds a way to make peace with his "worst investment", remains to be seen.
But one thing's for sure: the next time a billionaire buys a newspaper, they'd better be ready for a fight.
What do you think? Was Bezos right to call the Post his worst investment, or did he set it up to fail? Share your thoughts in the comments below.
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