Why This Millionaire Keeps a Castle Full of Princesses | Jon Ronson

Summary

Jon Ronson describes the opening of his new book The Castle and recounts a real-life story about a wealthy, older man who built an extravagant Gothic “castle” in the woods of Connecticut. The castle is used to lure young women—and other unsuspecting guests—into a highly curated, coercive setup.

The lure and the setup for “101 Princesses”

• Ronson’s son receives messages from the castle owner through a friend who met the owner on Tinder.
• With three friends, he is taken to a grand newly built Gothic castle.
• They expect a party, but are told there is no party.
• Instead, the owner intends to recruit them into his scheme: a “reality show” called “101 Princesses.”
• Guests are ordered into a basement costume area to dress as princesses and then film.
• As it becomes clear the operation is not genuine—along with strange interruptions (including a videographer pausing to serve the owner)—they refuse and are kicked out.

The owner’s lifestyle and “production” environment

Ronson highlights the castle’s “audacious” design—moats, towers, and themed rooms—alongside nearby attractions, such as:

• a pole-dancing nightclub
• underground botanical areas with a jacuzzi

Together, these reinforce the sense that the castle is a staged fantasy world.

Ronson’s involvement and escalating intimidation

• Intrigued, Ronson contacts the owner as a documentary filmmaker and visits the castle.
• He becomes the target of increasingly threatening messages.
• The owner claims he has enforcers (two named men) who will come after him if Ronson writes anything negative.
• Ronson frames this as a broader cat-and-mouse dynamic that intensifies as he learns more.

Background and money

Ronson reports the owner was the great-grandson of a Gilded Age steel magnate, explaining how he could finance the castle.

Control, ideology, and coercive “princessing”

Ronson says the owner promotes an ideology he calls “princessing.” The claim is that the goal is for women to develop romantic feelings with each other while the owner benefits. Ronson also connects the theme to modern constraints on men’s power—suggesting that certain fantasies of dominance no longer work the way they once did.

Possible legal and political entanglements

• Ronson says the owner tried to get him to sign a non-disclosure agreement (NDA).
• He suggests there may have been wider scrutiny or intimidation tactics.
• He also notes an FBI contact was reportedly involved, though he says he never fully understood what that meant.

After publication

Ronson concludes that now that the book is out, the owner appears worried and may have attempted legal action, while Ronson claims he carefully gathered information.

The video ends with Ronson promoting Patreon support for uncensored early episodes and special content.

Presenters / Contributors

• Jon Ronson (speaker)