Without intending to, and without even realizing it, September 28 of the year 2016 became a day that forever marked Sean Penn’s life. The irony of that day, as Penn himself described it, began when he was waiting for instructions for his meeting with El Chapo in a hotel where Mexico’s president, Enrique Peña Nieto, was also staying, preparing to attend the UN General Assembly. Quite the paradox.
Sean Penn’s Journey To Interviewing Joaquín “El Chapo” Guzmán
One of the reasons Sean Penn decided to interview Joaquín “El Chapo” Guzmán was to humanize him, to restore the “personhood” that, in Penn’s view, the Mexican government had stripped away during the brutal fight against drug trafficking that had claimed countless lives in Mexico and beyond.
The second reason, which deeply intrigued Penn, was to delve into the mind of “El Chapo” and uncover the origins of the “most wanted man.”

While waiting to meet the notorious capo, Penn’s mind was preoccupied with the news headlines, the Mexican press reports about lives lost to the drug war, and the daily horrors of burned and decapitated bodies turning up in cities across Mexico.
Penn was fully aware of the weight El Chapo carried, and amid that moral dilemma, he waited for his meeting, determined to reveal the truth—whatever that truth might be. For Penn, no one since Osama Bin Laden had so thoroughly captured the world’s attention, and it was precisely this complex knot that he sought to untangle. To him, every story has two sides.
A Secret Meeting
The first step in meeting the drug lord took place at a “Japanese restaurant” in New York—a meeting Penn knew could be his last chance to back out if reason prevailed.
The next step was in Los Angeles, where Penn was to meet the key contact between “El Chapo” and himself: Kate del Castillo, a prominent Mexican actress and producer known for her work in television, film, and theater. She gained widespread recognition for her role as Teresa Mendoza in the popular telenovela La Reina del Sur (The Queen of the South), which became a huge success in both Latin America and the United States.

According to Penn, he connected with Kate del Castillo through a mutual acquaintance—a producer involved in a project that Del Castillo and the drug lord had conceived: a film about El Chapo’s life. This production couldn’t begin like any other due to the obvious challenges posed by Guzmán’s situation. If the film was to be made under his supervision, maintaining contact would be extremely difficult.
Not long after, news broke that shook the world: Joaquín “El Chapo” Guzmán had escaped from a maximum-security federal prison for the second time. For Sean Penn, this event warranted an interview, an article, or something to uncover the secrets of “El Chapo.” He met with Kate through the unnamed producer to express his intentions, hoping Del Castillo could relay the message to Guzmán.

After a month of planning and logistics, the day of Guzmán’s “way of the cross” arrived: a flight from Los Angeles to Mexico City, followed by a drive from the airport to a hotel. Then, an hour-and-a-half-long journey in a convoy of armored cars, complete with a search of all cell phones and electronic devices. A stop at an anonymous airstrip, where two small planes—each manned by heavily armed security personnel—awaited. The two-hour flight over a jungle landscape was filled with conversation between Penn and Guzmán’s son, with Kate acting as interpreter.
Penn was struck by the trust El Chapo placed in them, as they weren’t blindfolded during the trip—something Penn attributed to Del Castillo’s influence.
What followed was countless, seemingly endless car rides that crossed rivers and landscapes resembling the Amazon rainforest, farmland, or a mix of both.
Seven hours later, they finally reached military checkpoints manned by Cartel soldiers, who sheepishly stepped aside upon recognizing the drug lord’s son.
Small villages and towns flashed by as they drove. Late at night, atop a mountain, amidst a convoy of cars and trucks, Sean Penn finally met “The Most Wanted Man,” who greeted him with a smile.
The Meeting
Once settled in, after eating and drinking, the conversation began. (Planned to be calm, there were no armed men in sight, and the atmosphere was surprisingly relaxed.) Sean Penn talked to Guzmán about his life and exploits: yes, his organizations in Haiti, yes, his friendship with Hugo Chávez, yes, a relative who once worked with the DEA. It was a desperate attempt to gain his trust, but it was necessary.
Sean Penn’s goal of portraying Guzmán as a human—a goal that clashed with the countless victims of the drug war—was more at stake than ever. Guzmán was charismatic, simple, calm, reserved about the government, smiling, a father. In every way, he was a person.
The preamble, which lasted almost all night, was filled with pleasant, varied conversation in an environment that Penn found oddly safe; despite being constantly aware of the risks, Guzmán’s security and composure extended to those around him.

Although the true purpose of Sean Penn’s interview was lost in the sensationalism and scandal that followed, the actor maintains that he couldn’t achieve the depth he desired. However, throughout his chronicle—published in Rolling Stone—he offered the world a different view of the planet’s most notorious drug lord. His account is clear, filled with timely observations that provide a raw perspective. What happened next was beyond anyone’s control.

