Criminally Yours: The 'Penn' Is Mightier Than The Sword

If El Chapo is sentenced in the U.S., he will be sent to a super max prison like Florence -- the likes of which no one has ever escaped.

justice-handcuffs-e1372182679824-300x286The world’s greatest drug felon, felled by an actor? That’s what headlines said last week when police captured El Chapo, “Shorty,” the infamous Mexican drug lord who recently escaped Mexico’s highest security prison by way of an underground tunnel rigged with a motorbike.

The escape was a huge embarrassment for the Mexican government and started an international dragnet to find him. But who, from the outside, spoke to the world’s most wanted man first? Sean Penn.

Among his many roles, Penn is now also a journalist and wrote a piece for Rolling Stone magazine on his interview with El Chapo that, coincidentally or not, ran on Jan. 9th, a day after El Chapo was recaptured by Mexican police.

Penn was brought into El Chapo’s inner circle because the drug lord was looking to connect with Hollywood glitterati to make his story into film. El Chapo had originally befriended Mexican telenovela star Kate del Castillo, trusting her to hook him up with the right people who would portray him kindly — not as a vicious killer, but as a poor kid from rural Mexico who grew poppy to survive. Violence was never the point, although sometimes, he conceded, it was necessary.

In his article, Penn chronicles the cloak-and-dagger arrangements that had to be made to meet El Chapo and his own paranoia at being surrounded by El Chapo’s henchmen, sometimes in the open, subject to drone detection by U.S. surveillance.

Did Penn do anything wrong in finding, interviewing, and basically humanizing the man who’s been the thorn in the side of the Mexican government and the DEA for decades?

Penn committed no crime. Granted, if publishing the article could be seen as aiding and abetting either El Chapo’s enterprise or his continued fugitive status, Penn could be harassed and even charged with a crime in Mexico, but he’s not there and the Mexican government now has its man. How the investigation and continued prosecution develop, however, will involve Penn.

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Both U.S. and Mexican authorities will want to bring Penn in for questioning. This will happen privately, and when it does, Penn should bring a lawyer.

Although they’ve got El Chapo in custody, they’ll want to milk Penn on every step he took in setting up the meeting, including quizzing Penn about all those he saw along the way or even just spoke with by phone. In order to identify suspects, the police will ask Penn to look at photos and listen to taped conversations. Even though El Chapo is in custody, he’s left behind a network of operatives who can continue the business without him.

Meanwhile, Mexico, this time, says it will extradite El Chapo. What’s the U.S. jurisdiction? The long reach of federal law. El Chapo is accused of trafficking drugs through our borders, thus we’ve got the right to prosecute him here.

His defense will be tough. In the interview with Penn, he made admissions that, “I supply more heroin, methamphetamine, cocaine, and marijuana than anybody else in the world. I have a fleet of submarines, airplanes, trucks, and boats.”

Even though the statements are hearsay, they can be used against him as admissions, an exception to the hearsay rule.

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Of course, he could take the route of many defendants brought into the federal system — cooperate against everyone he’s ever dealt with and trade off his info on the drug trade and graft in government and big business. That could get him a lesser sentence or maybe even a return to Mexico. There’s going to be a lot of politics being played.

But whether U.S. prosecutors will even be interested in cutting a deal with him depends on the strength and reliability of his insider knowledge and how willing they are to play with the devil, just as Sean Penn did.

One thing is for sure, if El Chapo is sentenced in the U.S., he will be sent to a super max prison like Florence — the likes of which no one has ever escaped.


Toni Messina has been practicing criminal defense law since 1990, although during law school she spent one summer as an intern in a large Boston law firm and realized quickly it wasn’t for her. Prior to attending law school, she worked as a journalist from Rome, Italy, reporting stories of international interest for CBS News and NPR. She keeps sane by balancing her law practice with a family of three children, playing in a BossaNova band, and dancing flamenco. She can be reached at tonimessinalw@gmail.com or tonimessinalaw.com.