The Contrarian: inside the life, lawsuits and liberties of Peter Thiel

As a new book on the tech messiah and PayPal founder hits shelves, Harry Shukman analyses one of Silicon Valley's most bothersome figures

One of the most expensive houses in Washington D.C., if you’re counting by the biggest sale in the last year, is at 2850 Woodland Drive, about ten minutes northwest of the city. It went for $13 million and looks like an American version of a French country home — Disneyland Versailles. It has seven bedrooms and ten bathrooms, two marble terraces, statue fountains, an outdoor pool, a 12-seat cinema, an acre of bucolic gardens, staff quarters, dressing rooms with enough wardrobe space to kit out an army, and ceilings that go all the way up into the stratosphere. 

It’s also close to Embassy Row: if the new owner of the Woodland Drive mansion stepped out onto one of their terraces and yelled at the top of their voice, the staffers inside the nearby British, Italian, and Bolivian embassies might be able to hear them. Who the owner was remained a mystery as they had gone to great lengths to buy the house from a former Trump official through a front company. But then last month, Washington insiders named Peter Thiel, the secretive German-born billionaire and Silicon Valley tycoon, as the proud new owner of a D.C. outpost. 

This is a tidy addition to his property portfolio. Thiel already owns pads in Manhattan and Los Angeles, as well as two adjacent waterfront mansions in Miami Beach ($18 million), another on the Hawaiian island of Maui ($27 million), and is constructing an apocalypse-proof 477-acre estate designed by the architect of Tokyo’s Olympic stadium in New Zealand ($13.5 million).

'American Disneyland'" Peter Thiel's new Washington D.C. pad

Thiel, 54, is a fascinating character who bothers and beguiles Americans in equal measure. He is worth around $3.3 billion, having co-founded PayPal, invested in Facebook, and then set up Palantir, a big data analysis company used by armies and police forces. His first major move into politics was in 2016, when he poured $1.5 million into Donald Trump’s campaign and spoke at the Republican convention. His line on Trump, after the unhinged 2016 campaign (“grab em by the pussy” now feels a long time ago), was to take him “seriously, not literally”

He has since given separate donations of $10 million to elect J.D. Vance in Ohio and Blake Masters in Arizona. His liberal opponents love to stick the knife in. “Unsmiling, solipsistic and at pains to conceal his forever wounded vanity,” sniffed a New York Times writer in a recent profile. “Comes across as singularly disagreeable, which is evidently the secret to both his worldly successes and his moral failures.”

What Thiel actually believes is the subject of endless debate, because he will not be interviewed on the record about his political views. He has written in the past about being libertarian, but a recent biographer said Thiel leans closer to authoritarian. Max Chafkin, who has tried to pin Thiel down in a new book, told Politico that his subject’s ideology is “super-nationalistic, it’s a longing for a sort of more powerful chief executive, or, you know, a dictator”.

To unlock this article, please subscribe. Benefits include:

  • Offers, benefits and access to exclusive clubs, restaurants, bars, gyms, hotels and handpicked brands
  • 2 Bookazines delivered to your door each year
  • 15% off selected brands online with the Gentleman's Journal Shop
  • Events — invitations to member-only events each year
  • Paywalled content — access to member-only password-protected online features
  • Your own Clubhouse membership card to redeem all the perks
Clubhouse Membership

Clubhouse Membership

Buy Now

Further Reading