Emails Show Hillary Clinton’s Top Aides Gushed Over Sean Penn

Chuck Ross Investigative Reporter
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Hillary Clinton’s top State Department aides gushed over actor Sean Penn in an April 2012 email, State Department records show.

“I am just so friggin proud of you,” Clinton’s chief of staff, Cheryl Mills, wrote in an April 26, 2012 email seemingly sent to Penn’s account. The email address is redacted but is listed as “CIA.”

“Do we call you mr ambassador laureate now?” Mills’ senior advisor, Caitlin Klevorick, wrote to Penn.

“Heartfelt congrats. We couldn’t be prouder!” she added.

The pair heaped praise on the small-statured Penn, who had just been awarded the 2012 Peace Summit Award from former Soviet President Mikhail Gorbachev for his work in Haiti following a disastrous 2010 earthquake. 


The email traffic has taken on new significance in light of news that Penn, a two-time Oscar winner, traveled to Mexico in October to meet with and interview Joaquin “El Chapo” Guzman, the notorious boss of the brutal Sinaloa drug cartel. Penn published a laudatory article about the visit for Rolling Stone. The piece, in which Penn calls Guzman “Robin Hood,” was published online late Saturday. (RELATED: Hollywood Actor Secretly Met With El Chapo Months Before His Arrest)

According to several reports, Penn’s visit to Guzman helped lead authorities to the fugitive. The drug trafficker had escaped from a Mexican prison in July and sought out a meeting with Hollywood actors in order to pitch a movie about his life. He was captured earlier this week, just before Penn’s article was published. According to some Mexican officials, Penn’s meeting with Guzman helped lead investigators to the criminal.

Hillary Clinton has not commented on Guzman’s arrest or on Penn’s visit. During an interview on Sunday, President Obama’s chief of staff, Denis McDonough, said that Penn’s “so-called interview” with Guzman “poses a lot of very interesting questions, both for him and for others involved in this.”

Other politicians, such as Republican presidential candidate Marco Rubio, called the interview “grotesque.” (RELATED: Marco Rubio: Sean Penn’s Interview With El Chapo Is ‘Grotesque’)

Mills’ praise in for Penn in their 2012 email exchange was not one-sided.

“Ur the coolest,” the actor wrote to her in a response email. He added that he was at a jazz club in Chicago at the time.

“Great time to get your msg. Thank you Cheryl. Love-s.”

Mills forwarded the email traffic to Clinton and suggested that she write a note or call Penn to congratulate him on the award.

“We should do a note or have you call Sean who was just awarded the 2012 Peace Summit Award from former Soviet President Mikhail Gorbachev, who was joined on stage by the Dalai Lama and former Polish President Lech Walesa,” Mills suggested.

“Ok. Can you talk?” Clinton replied.

Though Clinton and company’s coziness with Penn preceded his visit to Guzman, the actor had already established an impressive resume of supporting violent foreign enemies of the U.S. Penn was a friend and staunch defender of Venezuelan dictator Hugo Chavez.

Penn once called for the arrest of people who called Chavez a dictator. And when Chavez died in 2013, Penn wrote in eulogy: “And poor people around the world lost a champion.”

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