El Chapo was a genius at trafficking drugs—but really awkward at flirting

Kate del Castillo, the recipient of El Chapo’s decidedly teenage text messages.
Kate del Castillo, the recipient of El Chapo’s decidedly teenage text messages.
Image: Reuters/Kevork Djansezian
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Joaquín “El Chapo” Guzmán has been long known as a calculating businessman whose organization exports drugs to the US by the ton, racking up thousands of casualties along the way.

But the world is now getting a glimpse of Guzmán’s more romantic side through a lengthy exchange (link in Spanish), published in Mexican newspaper Milenio, of BlackBerry messages with Kate del Castillo, the Mexican actress who arranged his now infamous interview with Sean Penn.

It’s hard to reconcile the two personas. The messages show the powerful kingpin as an obsequious—and not very eloquent—suitor. Their very existence also suggests El Chapo, who was probably the most sought-after criminal on earth at the time he wrote them, was not as cunning in romance as he was in business. The communications eventually ended up in government hands, helping authorities apprehend him.

The man known to execute subordinates for late drug shipments bent over backwards to accommodate his beau’s time constraints. “A question: please tell me at what time I can send you a message so I don’t distract you from your busy schedule,” he writes in one message. He later asks del Castillo what her favorite food is so he can have it ready for her when she comes to visit. Among his other classy one-liners:

“Good afternoon, how is the finest and most intelligent woman in the world, whom I admire a lot?”

“I’ll have everything super for you so you won’t want for anything, because that would make me feel really bad. I will take better care of you than of my eyes.”

“I’m more excited about you than I have ever been about anything.”

The exchange also shows El Chapo getting into a highly detailed discussion with one of his subordinates about what make and color of mobile phone to buy for del Castillo so she can communicate with him. “Which one looks prettiest?” he asks, and at another point, “Doesn’t it come in pink? If it doesn’t come in pink buy a silver one.”

A psychological profile by experts at Mexico’s attorney general’s office after Guzmán was first captured found him to be highly dangerous, egocentric, and incapable of feeling guilt. They link his “tenacity” to feelings of inferiority due to his short height, 1.55 meters (barely over five feet).

But, they also noted, “his need for social interaction can lead him to the loss of his most precious good, which is freedom,” according to a copy of the profile (Spanish) published by Mexican columnist Miguel Badillo.

Psychology experts say such apparent contradictions are not uncommon among psychopaths. In fact, they can appear to be quite charming. “It’s literally a mask,” said Terrance Lichtenwald, a forensic psychologist who has analyzed criminals linked to Mexican cartels.

That might explain why Guzmán allowed himself to banter with del Castillo, despite the risk of exposing his location. Around that time, he reportedly left his hideout to get an implant (Spanish, paywall) to solve his erectile dysfunction.

For her part, del Castillo replied to El Chapo’s stilted declarations in a similar vein. “I’m so touched that you say you’ll take care of me, nobody has ever taken care of me, thank you!”she said after he told her he’d take better care of her than of his eyes. “I haven’t slept much since I saw you, I’m excited about what’s happening between us… It’s true. It’s the only thing I think about…”

The exchange could turn sour for her too. Mexican authorities have called her to testify about her dealings with Guzmán, including new texts (Spanish) published by Mexican newspaper El Universal that suggest she was seeking to get El Chapo involved in her tequila company.