How Did Sean Penn's Secret Interview with El Chapo Trigger a DEA Manhunt and Nearly Get Him Killed?

A new global interest has been ignited in Joaquín "El Chapo" Guzmán, after reports emerged that more than 17 relatives of the drug mafia were granted entry into the US under a covert deal brokered by the Trump administration. However, the US government has yet to confirm the 'secret deal', although authorities in Mexico have attested to the move.

The revelation has caused a stir in Washington and beyond, highlighting once again the murky intersections of politics, crime, and the media.

But this isn't the first time El Chapo's name has dominated headlines. Nearly a decade ago, a secretive and risky interview between the fugitive kingpin and Oscar-winning Hollywood actor Sean Penn triggered not only diplomatic drama but nearly resulted in the actor being caught in a crossfire during a failed raid in the Mexican highlands.

A Meeting in the Mountains

In October 2015, Sean Penn, alongside Mexican actress Kate del Castillo, travelled deep into Sinaloa to meet El Chapo. Guzmán had recently escaped from a Mexican prison for the second time, vanishing through a mile-long tunnel built right into his cell. While on the run, he expressed a desire to make a film about his life — and saw del Castillo as the one to help him do it.

Penn, seizing the opportunity for an exclusive interview, joined the trip. The journey was anything but easy — two flights followed by a tough seven-hour drive through cartel-controlled mountains eventually brought them face to face with one of the world's most wanted men.

Unbeknownst to Guzmán, US intelligence — including the DEA (Drug Enforcement Administration) and NSA (National Security Agency) — had tapped his communications. As journalist Alan Feuer later noted in his book El Jefe, the NSA was eavesdropping on the drug lord as he Googled Penn to vet him before agreeing to the meeting.

The Meeting Could Have Been a Disaster

The secret rendezvous took place at one of Guzmán's remote hideouts. According to reports, Penn intended to write an article for Rolling Stone, which he later did, but he had not yet disclosed this to El Chapo. Anyone familiar with Guzmán's history will know that the man had a reputation for brutal retaliation when crossed, and paranoia ran high in his ranks.

What Penn didn't realise was that Mexican marines, working with US intelligence, were reportedly already closing in. Reports suggested that a raid was scheduled for the very night Penn and del Castillo met El Chapo. According to US officials, it was only delayed by a severe storm — a stroke of luck that likely saved their lives.

According to Feur, one DEA official reportedly summarised the mood at the time: 'F--k Sean Penn, the raid goes on.' It was only Mother Nature that stayed their hand.

Sean Penn Regretted His Rolling Stone Article

Three months after the meeting, El Chapo was captured in January 2016 in Los Mochis, Sinaloa. While Mexican authorities credited Penn's meeting as a crucial lead, others, including author Feuer, argue they already had Guzmán's location and were closing in regardless.

Penn's article for Rolling Stone, published shortly after the arrest, caused a media storm.

Critics slammed the magazine for giving a platform to a known criminal, and Penn faced backlash for romanticising and glamorising an encounter with a fugitive. Later, he admitted in an interview with Charlie Rose that he had 'terrible regret.'

'Let me be clear. My article has failed,' the actor said. 'I have a regret that the entire discussion about this article ignores its purpose, which was to contribute to this conversation on the war on drugs.'

Today, El Chapo is serving a life sentence in the US's most secure prison, but his story in various forms continues to haunt politics, border policy and popular culture as well. Sean Penn's wild interview remains a key chapter in a saga that still unfolds with surprising new developments — from prison movie pitches to backdoor deals in Washington.