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Peter Thiel: The Silicon Valley billionaire made big—and early—bets on Trump and J.D. Vance. What did he see that so many didn’t?

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News release from The Free Press

Triumph of the Counter-Elites

Bari Weiss and entrepreneur Peter Thiel talked this week in Washington, D.C.

On Tuesday night, Donald Trump announced that the richest man in the world, Elon Musk, along with the entrepreneur Vivek Ramaswamy, will head a new initiative in the Trump administration: the Department of Government Efficiency, or “DOGE.”

Internet meme culture has now landed in the White House. Dogecoin is a memecoin—and if you don’t understand that sentence, fear not—I am sure Nellie will cover it in TGIF tomorrow.

But what the announcement solidifies—if Trump’s win hadn’t already—is the triumph of the counter-elite.

A bunch of oddball outsiders ran against an insular band of out-of-touch elites supported by every celebrity in Hollywood—and they won. They are about to reshape not just the government, but also the culture in ways we can’t imagine.

How they did that—and why—is a question that I’ve been thinking about nonstop since Tuesday.

And there was one person, more than any other, who I wanted to discuss it with. He is the vanguard of those antiestablishment counter-elites: Peter Thiel.

If you listened to my last conversation with the billionaire venture capitalist a year and a half ago on Honestly, you’ll remember that Peter was the first person in Silicon Valley to publicly embrace Trump in 2016. That year, he gave a memorable speech at the Republican National Convention that many in his orbit thought was simply a step too far.

He lost business at Y Combinator, the start-up incubator where he was a partner. Many prominent tech leaders criticized him publicly, like VC and Twitter investor Chris Sacca, who called Thiel’s endorsement of Trump “one of the most dangerous things” he had ever seen.

A lot has changed since then.

For one, Thiel has taken a step back from politics—at least publicly. He didn’t donate to Trump’s campaign. There was no big RNC speech this time around.

But the bigger change is a cultural one: He’s no longer the pariah of Silicon Valley for supporting Trump. There’s Bill Ackman, Marc Andreessen, David Sacks, Shaun Maguire, and Elon Musk, among many other tech titans who have joined the Trump train.

On the surface, Thiel seems full of contradictions. He is a libertarian who has found common cause with nationalists and populists. He invests in companies that have the ability to become monopolies, and yet Trump’s White House wants to break up Big Tech. He is a gay American immigrant, but he hates identity politics and the culture wars. He pays people to drop out of college, but still seems to venerate the Ivy League.

But perhaps that’s the secret to his success. He’s beholden to no tribe but himself, no ideology but his own.

And why wouldn’t you be when you make so many winning bets? From co-founding PayPal and the data analytics firm Palantir (which was used to find Osama bin Laden) to being the first outside investor in Facebook—Thiel’s investments in companies like LinkedIn, Palantir, and SpaceX have paid off, to say the least.

His most recent bet—helping his mentee J.D. Vance get elected senator and then on the Trump ticket—seems also to have paid off. The next four years will determine just how high Thiel’s profit margin will be.

On Honestly, Thiel explains why so many of his peers have finally come around to Trump; why he thinks Kamala—and liberalism more broadly—lost the election; why the Trump 2.0 team, with antiestablishment figures willing to rethink the system, will be better than last time. We talk about the rise of historical revisionism, the blurry line between skepticism and conspiracy, and his contrarian ideas about what we might face in a dreaded World War III.

Click below to watch the full-length video.

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conflict

Trump tells Zelensky: Accept peace or risk ‘losing the whole country’

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Quick Hit:

President Donald Trump warned Ukrainian President Volodymyr Zelensky that he risks losing Ukraine entirely if he continues resisting a peace settlement. Trump said Moscow is ready for peace, but Kyiv’s refusal to recognize Crimea as Russian territory could derail the effort.

Key Details:

  • Trump said Zelensky “can have Peace or… lose the whole Country” and claimed Russia is ready to make a deal.
  • Zelensky reiterated Ukraine’s refusal to recognize Russia’s occupation of Crimea, a key sticking point in current peace talks.
  • White House press secretary Karoline Leavitt said Trump is frustrated and warned peace efforts may end if no deal is reached this week.

Diving Deeper:

President Trump issued a blunt warning to Ukrainian President Volodymyr Zelensky on Wednesday, saying the Ukrainian leader must choose between accepting peace or facing the collapse of his nation.

“He can have Peace or… fight for another three years before losing the whole Country,” Trump posted on Truth Social. The statement followed Zelensky’s firm declaration that Ukraine “will not legally recognize the [Russian] occupation of Crimea,” a stance at odds with a proposed peace plan under discussion in London between U.S., British, and European officials.

Trump blasted Zelensky’s comment as damaging, declaring, “Crimea was lost years ago under the auspices of President Barack Hussein Obama, and is not even a point of discussion.” The president added that such rhetoric undermines delicate peace negotiations.

Speaking from the Oval Office, Trump said, “I think Russia is ready,” referring to a peace deal, but questioned whether Ukraine is. Kyiv reportedly signed on to a Trump-proposed ceasefire more than a month ago. Trump hinted that progress has been stymied by Zelensky’s reluctance to compromise.

Despite Russian officials signaling a desire to prolong negotiations—with Kremlin spokesman Dmitry Peskov dismissing Trump’s efforts as “futile”—Trump maintained optimism, stating, “I think we have a deal with Russia… we have to get a deal with Zelensky.”

White House press secretary Karoline Leavitt said Trump’s patience is wearing thin. “President Zelensky has been trying to litigate this peace negotiation in the press, and that’s unacceptable,” she said, calling for closed-door diplomacy. “The American taxpayer has funded billions… enough is enough.”

Trump, 78, has consistently criticized Obama for allowing Russia’s 2014 annexation of Crimea to go unanswered. Now, under the Trump administration’s push for peace, a senior official revealed the U.S. is considering recognizing Crimea as Russian territory—a reversal of longstanding American policy based on the 1940 Welles Declaration.

Still, Trump refrained from criticizing Vladimir Putin directly, instead blaming Zelensky for inflammatory statements. “He has nothing to boast about!” Trump said, referencing a heated Feb. 28 Oval Office exchange with Zelensky and Vice President JD Vance.

“I have nothing to do with Russia,” Trump wrote, “but have much to do with wanting to save… five thousand Russian and Ukrainian soldiers a week.”

Trump warned that time is running out: “We are very close to a Deal, but the man with ‘no cards to play’ should now, finally, GET IT DONE.”

With London talks underway and pressure mounting, officials hinted that if no agreement is reached this week, the U.S. could walk away from its efforts in Eastern Europe. Asked whether Trump is ready to give up, Leavitt said, “Not by the end of the day today… but the President… needs to see this thing come to an end.”

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Entertainment

Pedro Pascal launches attack on J.K. Rowling over biological sex views

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Quick Hit:

Pedro Pascal, star of HBO’s The Last of Us, ignited backlash this week after publicly hurling an expletive-laced insult at author J.K. Rowling in response to her support for a landmark UK ruling that upheld the legal definition of sex as biological. Rowling celebrated the decision, which affirms the rights of women to single-sex spaces—a view shared by many who advocate for the safety and integrity of women’s rights. Pascal, a vocal progressive and LGBTQ+ activist, labeled Rowling a “heinous loser,” aligning himself with calls to boycott HBO’s upcoming Harry Potter reboot.

Key Details:

  • Pedro Pascal responded on Instagram to Rowling’s post celebrating a UK court ruling that legally defined “sex” as biological.

  • Pascal echoed an activist’s call for a fan-led boycott of the Harry Potter reboot, saying Rowling’s stance was “heinous LOSER behavior.”

  • HBO has downplayed concerns of a boycott, citing the blockbuster success of Hogwarts Legacy despite similar activist campaigns.

Diving Deeper:

The latest clash in the culture war surrounding Harry Potter author J.K. Rowling and the trans activist movement reached a new level of hostility this week when actor Pedro Pascal, a key face of HBO’s entertainment slate, stooped to name-calling on social media. His remarks came in response to Rowling’s defense of the United Kingdom’s recent court decision, which reaffirmed that sex, under British law, means biological sex—a ruling many women’s rights advocates hailed as a long-overdue step toward protecting vulnerable female spaces such as shelters, hospital wards, and sports.

Rowling, whose views on the importance of distinguishing biological sex from gender identity have made her a target of trans activists for years, posted a pointed but unapologetic reaction: “I love it when a plan comes together.” She added, “I get the same royalties whether you read [my books] or burn them. Enjoy your marshmallows!”

In the comments of a post by activist Tariq Ra’ouf—who had attacked Rowling and promoted a boycott of HBO’s Harry Potter reboot—Pascal added his own vulgar commentary: “Awful disgusting SHIT is exactly right. Heinous LOSER behavior.” While Pascal did not explicitly mention Harry Potter, the post he endorsed included calls to tank all future franchise content, including theme parks and merchandise.

Pascal’s involvement with HBO places the network in a difficult position. As the Emmy-nominated co-lead of The Last of Us, one of HBO’s crown jewels, Pascal’s comments are being widely interpreted as an implicit endorsement of the boycott. While HBO has attempted to downplay the activist push, the tension is palpable. Casey Bloys, HBO’s chief content officer, previously noted that the 2023 video game Hogwarts Legacy, which also faced calls for boycotts due to Rowling’s views, still became the year’s top-selling game.

Pascal’s activism is personal as well as political. His sister, Lux Pascal, publicly transitioned in 2021, and he has frequently signaled support for trans activism. At the UK premiere of Marvel’s Thunderbolts, Pascal wore a shirt that read “Protect the Dolls,” a slogan popularized in trans activist circles.

Rather than “heinous,” Rowling’s remarks represent a reasoned defense of biological reality and a pushback against an increasingly aggressive ideology that demands conformity and punishes dissent. Her critics, like Pascal, resort to vulgarity and character attacks instead of engaging with the substance of her argument. But Rowling has stood firm in supporting women’s rights and advocating for clarity in laws that impact everything from sports to safety in single-sex spaces—positions grounded in truth, not hate.

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