The Slatest

Sean Penn’s Castration Fears and Other Revelations From His “El Chapo” Piece

US actor Sean Penn gestures as he speaks during a working session for “Action Day” at the COP21 United Nations conference on climate change in Le Bourget on December 5, 2015.

Photo by ERIC FEFERBERG/AFP/Getty Images

Sean Penn got a huge scoop when he managed to sit down with the world’s most powerful drug lord for seven hours. He even got a chance to ask him some follow up questions via BlackBerry Messenger. But considering he never got the proper sit-down interview he was promised, Penn ends up thrusting himself in the middle of a story that turns out to be as much about the actor-turned-gonzo-journalist than about the head of the Sinaloa cartel. The piece amounts to a lost opportunity to get inside the head of one of the world’s most notorious criminals. But we do learn a few things about Penn.

Penn is surprisingly illiterate about technology—and seemingly proud of it:

It’s a clandestine horror show for the single most technologically illiterate man left standing. At 55 years old, I’ve never learned to use a laptop. Do they still make laptops? No fucking idea!

Finally a respite from the cyber technology that’s been sizzling my brain and soul. We sit within quietude of fortified walls that are old New York hotel construction, when walls were walls, and telephones were usable without a Ph.D.

Penn likes to use the word “paradox”:

We quietly make our plans, sensitive to the paradox that also in our hotel is President Enrique Peña Nieto of Mexico.


As we exit onto 55th Street, the sidewalk is lined with the armored SUVs that will transport the president of Mexico to the General Assembly. Paradoxical indeed, as one among his detail asks if I will take a selfie with him.

Flash frame: Why is this a paradox? It’s paradoxical because today’s Mexico has, in effect, two presidents. 

He is also a fan of the word fuck:

The trust that El Chapo had extended to us was not to be fucked with.

The guy runs a multibillion-dollar business with a network of at least 50 countries, and there’s not one fucker down there in the jungle with him who speaks a word of friggin’ English?


I ask myself, How in the fuck does anyone run a business that way?!

He doesn’t speak much Spanish:

My own Spanish is weak at best. By day, and put on the spot, I’m pretty restricted to hola and adios. By night, with perhaps a few beers, I can get by, speaking and listening slowly.

Penn only likes to go fast if he’s the one driving:

With each message received, the needle on the speedometer rises; we are cruising at well over 100 miles per hour. I like speed. But not without my own hands on the wheel.

He doesn’t really have a concept of how much things are worth:

He boards beside me, designated among our personal escorts to see his father. He’s handsome, lean and smartly dressed, with a wristwatch that might be of more value than the money housed by the central banks of most nation-states. He’s got one hell of a wristwatch.

He has a vivid fear of castration:

I throw my satchel into the open back of one of the SUVs, and lumber over to the tree line to take a piss. Dick in hand, I do consider it among my body parts vulnerable to the knives of irrational narco types, and take a fond last look, before tucking it back into my pants.

Penn didn’t receive any monetary compensation for the article:

“How much money will you make writing this article?” he asks. I answer that when I do journalism, I take no payment. I could see that, to him, the idea of doing any kind of work without payment is a fool’s game.

He is not shy about sharing embarrassing details:

At this moment, I expel a minor traveler’s flatulence (sorry).

Penn doesn’t mind badgering to get what he wants:

I go Full-Trump-Gringo on Kate, battering her daily by phone, text and encrypted email.