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The sensational real story behind the Oscar winner's meeting with the Mexican drug lord, and the famous Hollywood figure who was pulling the strings back in Hollywood.

Uncover the intricate web of criminal enterprises, from notorious mob families to high-stakes heists, as we delve into the compelling stories behind the criminal masterminds and law enforcement efforts to bring them to justice.

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00:00Joaquin Archivaldo Guzman, the richest,
00:04most feared drug lord in the world,
00:07dreamed of his name in lights.
00:10Hollywood was going to immortalize him.
00:14He stood only 5 feet 6 inches tall.
00:17But with help from two glamorous movie starlets
00:20and an Oscar-winning actor, El Chapo
00:23would be bigger than Pablo Escalar, bigger than Scarface.
00:30Then, suddenly, the lights went out.
00:34And it was Hollywood's rebel with a thousand causes
00:37who flicked the switch.
00:39If any Hollywood celebrity would get mixed up
00:41in a caper like this, it would have to be shot then.
00:44It's crazy.
00:45It's crazy.
00:48It's crazy.
00:49It's crazy.
00:50It's crazy.
00:51It's crazy.
00:52It's crazy.
00:53It's crazy.
00:54It's crazy.
00:55It's crazy.
00:56It's crazy.
00:57January 8, 2016.
01:00Mexican Navy Special Forces, Army, and Federal Police
01:04converge on a house in northern Sinaloa, Mexico.
01:08Inside is the most wanted man in the Western Hemisphere,
01:12a man considered to be the wealthiest and most
01:14dangerous drug trafficker in the world,
01:17a man who's embarrassed the Mexican government
01:20by escaping from two of its maximum security prisons.
01:27Amid the gunfire, the suspect slips away
01:29through a hidden tunnel.
01:31But he's captured in the street after hijacking a car.
01:36A few hours later, the suspect is paraded for the media.
01:42Then he's returned to the prison he'd escaped
01:45from six months earlier.
01:50Joaquin Archivaldo Guzman, public enemy number one,
01:54has come to the end of his last tunnel.
01:57And the saga of the murderous drug lord they call El Chapo,
02:01seems to finally be over, but not so fast.
02:06Within hours of his capture, a bizarre only in Hollywood story
02:10would emerge about what transpired while El Chapo was on the run.
02:15If his capture had all the elements of an action movie,
02:18this story has even more.
02:21There's action all right, along with mystery, drama,
02:25intrigue, romance, even comedy.
02:33And there's a woman in the picture.
02:35In fact, there are two.
02:39But the big news is his male co-star, a two-time Oscar winner.
02:43As the official story has it, Sean Penn met the fugitive El Chapo for an interview
02:53that he hoped would reopen a dialogue about drugs in America.
02:57He came away with something very different.
03:08And the story of what really happened behind the scenes,
03:11who was involved, and what everyone got from it, has never been told.
03:16It's the kind of story you really couldn't make it up.
03:20Hollywood actors sitting in a five-star hotel gets this idea to go interview a drug lord
03:27for a rock and roll magazine, and then the police capture the guy who's on the lam,
03:33who escaped from prison by digging a tunnel through his shower.
03:37I mean, you really couldn't make this up.
03:42El Chapo, or Shorty, because he never grew above five-foot-six,
03:47and Sean Penn, who settled in at five-foot-eight, lived dramatically different lives.
03:53But in some ways, theirs were parallel lives.
03:56And the fact that they'd star together in this real-life tragicomedy was almost predestined.
04:03Chapo is a mythological figure in Mexico.
04:06He's like Robin Hood.
04:07In Mexico, there are 32 families that own the country,
04:10and if you're not born into one of those families, your chances of success are rare or nil.
04:15And so he is seen as a folk hero because he was able to break out of his impoverished situation
04:21and become a megastar.
04:23Sean Penn's a pretty unusual character.
04:25I can't speak for middle America, but my guess is that he's perceived as somebody who's one of those
04:32Hollywood liberals, who's a little bit of a loose cannon, who is kind of this rogue guy who's going
04:39off and doing kind of crazy things. But he doesn't care what middle America thinks for sure anyway.
04:46El Chapo was born into a poor family, either on Christmas Day 1954 or in 1957.
04:55The records are sketchy. In Sinaloa State, Mexico.
04:58A small town called La Tuna. Sean Penn was born in 1960 into a well-to-do showbiz family and raised on
05:10Point Dune in exclusive Malibu, California, not far from Tuna Canyon.
05:15Sean Penn does come across as this really kind of scrappy, very intense guy. And you would think
05:22that he's growing up on the sort of mean streets. But actually, he had a pretty lovely childhood.
05:27He grew up in kind of paradise, really. He had a loving family. He had two nice brothers. They
05:33made home movies together. But he did have this kind of dark side to him and there were issues there.
05:38El Chapo's father was a cattle rancher who farmed opium poppies on the side.
05:44Sean Penn's father was an actor and director who was blacklisted in the 1950s.
05:50And really, he was something of a war hero during World War II. But he was blacklisted after he
05:54wouldn't name names during the Red Scare. After he was blacklisted, he had to turn from acting to
05:59directing to make a living. And while Sean Penn got his first TV role at 13,
06:04his father cast him in Little House on the Prairie. El Chapo was 15 when he started up his first marijuana
06:11plantation.
06:14Look, as far as people there are concerned, is that it's very empty of America to blame
06:21these people that had no other option but to sell drugs.
06:25The problem with drugs is that the immense amount of money that it brings
06:31corrupts everything from the corner cop to the president.
06:35You know, yeah, you could do something else. You know, that's an excuse. But I'll tell you,
06:40Sinaloa is a state in Mexico that has always been famous for this. Before Chapo,
06:45you had Caro Quintero. And before him, you had the...
06:48That's El Chapo.
06:54By the early 1980s, Sean Penn's future interview subject, El Chapo, was coordinating shipments
07:00for one of Mexico's major drug lords. Sean Penn was making his mark on Hollywood in the movie
07:06Fast Times at Ridgemont High.
07:08He started out as this very iconic character, as Jeff Spicoli, which is sort of this image of this pothead,
07:14idiot guy. 1985 was a game-changing year for both men. The murder of an American DEA agent led to the
07:23arrest of the leader of the Guadalajara drug cartel and El Chapo's rise as a drug trafficker.
07:30And an encounter with a pop star led to the near downfall of Sean Penn.
07:35It was January on a Hollywood soundstage when he met Madonna. She was shooting the video for
07:47Material Girl, the song that would define her image. So she was this kind of sexual revolutionary who
07:53really thrived on attention and drama, really. And he was this kind of Hollywood kid who, you know,
07:59had a bit of a chip on his shoulder. And it was an incredibly volatile mix.
08:02They were married eight months later outdoors in Malibu.
08:06The wedding took place on her 27th birthday and just a day before his 25th. There was a huge amount
08:12of press attention. There were photographers circling in helicopters above. And legend has
08:16it that Sean fired off a pistol at one of the helicopters.
08:20The marriage ended after four years.
08:23But in his time with Madonna, Penn's life and reputation changed drastically.
08:29His public image went from intense, brilliant young actor to spoiled, violent Hollywood brat.
08:37Sean and Madonna back in the 80s really were the hot couple of Hollywood. They were the kind of Kim
08:42and Kanye's or the Brad and Angelina's of the day. They really were tabloid fodder and people just
08:47couldn't get enough of their crazy love story. Madonna really lapped up the attention. But for Sean,
08:52he was just too much of a hothead back then to really handle it. He lashed out at the paparazzi.
09:00He threw rocks at them.
09:03He served jail time after punching someone on set. So it really was a very, very dark time for Sean.
09:09By the end of the 80s, the man who'd be Sean Penn's second most controversial partner was running his
09:19own Sinaloa cartel, running drugs through 60 tunnels he'd built between Tijuana and San Diego.
09:26Meanwhile, Sean Penn was running from his tabloid image. He announced he'd quit acting because he really
09:33wanted to direct. He'd really had enough by that point of all of the attention, all of the tabloid
09:38headlines and the whole Hollywood scene. And he realized that he'd just become a bit of a joke.
09:45He wanted to be taken seriously. 1993, El Chapo was arrested and sentenced to 20 years for drug
09:53trafficking and bribery. That year, Sean returned to acting in Carlito's way, playing the attorney for a
10:01drug kingpin. With his shaved forehead and permed hair, he was unrecognizable.
10:08And with his next role, the real-life Sean Penn took on some changes as well.
10:14His desire to be taken seriously in the real world had led to a new career as a liberal Hollywood
10:20activist. He had his wild child period, and he's come through that. And I think he's matured
10:27into and channeled that sort of wild child part of him to do really serious issues in his acting,
10:32as in Dead Man Walking, which takes on the issue of capital punishment, the death penalty. And he's
10:38also matured into his directing roles. And he has, in parallel, become an activist, a social activist.
10:46But perhaps nothing affected Sean Penn more than the death of his father, Leo, in 1998. Sean remembered
10:57him as a patriot whose country turned against him. And it seems that that's what set Sean off on his
11:03own journey to become a revolutionary, to become an activist. And with the new century and administration,
11:10Sean Penn's activism was about to take a turn that would culminate in his meeting with El Chapo.
11:24In 2001, to the great embarrassment of Mexican authorities, El Chapo bribed some guards and
11:30escaped from the maximum security Puento Grande prison in a cart of dirty laundry. He'd remain on the run for
11:3713 years, picking up folk hero status among Mexico's poor, a Robin Hood helping villages with roads and
11:45schools, while his cartel expanded from cocaine and marijuana to heroin, ecstasy, and crystal meth.
11:54That year, George W. Bush took office, and Sean Penn began running in a direction that would
12:00eventually lead straight into El Chapo's arms, or at least that handshake.
12:07With George winning, and then I think the twists and turns of political events where suddenly you're,
12:13you know, you have 9-11 happen, and then suddenly it's over going to Afghanistan, which makes sense,
12:17and then suddenly you have this strange pivot where you're going into Iraq, which doesn't make sense.
12:22You know, I think Sean saw the folly in the Iraq war long before, you know, mainstream media ever did.
12:28With Hollywood supporters cheering him on, Sean Penn would pull so many left-wing political stunts,
12:34we could easily forget he had time to pick up two Oscars for best actor along the way.
12:42He's very involved in matters of social justice and politics, and he also sometimes
12:48sees himself as a kind of self-appointed emissary of change in certain cases.
12:54Sean, should you guys be out killing a princess somewhere?
12:58It seems that acting's never quite been enough for him. He wants to be a revolutionary. He wants
13:03to be a real-life hero.
13:04I think whether Sean was or wasn't an actor, I think he would still be an activist.
13:13December 2002, Sean Penn visits Iraq to protest the Bush administration's plan for a military strike.
13:202003, back to Iraq. 2005, Iran. Both times as celebrity reporter for the San Francisco Chronicle.
13:30The editor who gave Sean Penn his press credentials was Sharon Stone's ex-husband, Phil Bronstein.
13:36So he knew a little something about the whole Hollywood world and the power of celebrity.
13:41And even though there was quite a lot of backlash from real journalists who went berserk when Sean
13:46Penn went to Iraq and Iran, Phil knew that it would get the clicks.
13:51And these days in journalism, clicks is really what it's all about.
13:562007. Penn delivers this memorable message to President Bush at a town hall meeting in Oakland, California.
14:05We cower as you point your fingers, telling us to support our troops.
14:09Will you and the smarmy pundits in your pocket, those who...
14:14Those who bathe in the moisture of your soiled and blood-soaked underwear can take that noise and shove it.
14:24That same year, Sean Penn meets with Venezuela's president, Hugo Chavez, in Caracas.
14:29The Marxist Chavez praises Penn for urging Americans to impeach President Bush.
14:35It's this relationship that leads to a public confrontation.
14:39One that reveals a split, not only among Sean Penn's viewing public, but his colleagues in Hollywood.
14:47I compare Chavez to any devil that has been out there or there still is there.
14:52When I see him together and I couldn't believe it and I tried to get a hold of Sean.
14:58He never wanted to talk to me. We co-starred in colors and we got along great, great.
15:04You know, he's an amazing actor and we never spoke politics.
15:08I went to pick up my mother at the LAX and she was coming from Miami.
15:12And all of a sudden I see him, I see Sean Penn there waiting for the suitcases.
15:17I gotta say that I did get a little bit of anxiety and oh my God, oh my God, what do I do?
15:24Should I go to him and finally talk to him? Oh my God, you know, because I know his temper,
15:29especially when our issues that, you know, that like this about politics where, you know,
15:37they destroy people's lives. So I said to him, you know, it must be great to
15:42grow up as a communist the way you live. One thing led to the other one.
15:50He called me a pig and I called him a communist .
15:55No, Sean is far from a . Sean's actually one of probably the truly most
16:04giving and truly charitable and truly decent human beings I've ever met in my life. He's far from a .
16:11I turn around to walk towards my mother and he's screaming at me.
16:17Everybody there was so quiet. Must have been in shock. People were like, they couldn't believe
16:24what they were seeing. And I just turned around and I screamed with all my strength, communist .
16:34And I continued walking and that was it. My mother, she started clapping.
16:41A communist . Right. He's usually on the side of the left in some way and often, you know,
17:00in opposition to whatever the position of the American government might be. And along the way,
17:04Sean Penn plays real life action hero. In the wake of Hurricane Katrina,
17:10he flies to New Orleans and personally pulls people out of the floodwaters.
17:15He brings along two macho accessories, a shotgun and a personal photographer.
17:21Critics call it a PR stunt. If it is, the stunt backfires when his dinghy springs a leak.
17:32Then there's Haiti. After the 2010 earthquake, Penn wings into the rescue. He brings in medicine and
17:39doctors. Personally runs a camp for thousands of homeless. He moves there, always armed with a
17:46Glock pistol in his waistband. 2012 in Pakistan, visiting flood stricken villages.
17:542013 helps free an American from a Bolivian prison. He's not afraid to go down and get dirty and make
18:02things happen in the name of helping people. I think anybody that was sitting back, you know,
18:06behind a news desk or, you know, sitting in an air conditioned room making fun of Sean Penn for going
18:12out and helping people. I think those people need to look themselves in the mirror.
18:18I think his heart is in the right place and good for him, you know. He decided to do something social with
18:24his fame. And for that, you got to give him credit. I'm not kissing his ass. I personally, I think his
18:30politics is whack. But, you know, he means well. He at least is trying to do something with his fame.
18:38And for that, here, for that, I take my hat off to Spicoli.
18:46And then comes February 22, 2014, the fifth anniversary of the night Sean Penn received
18:56his second Oscar for Best Actor. El Chapo, on the run since 2001, is trapped in a beachside condo
19:04in Mazatlan, Sinaloa. When the feds bust in, he's naked in bed with his beauty queen wife and an AK-47.
19:12He's arrested and taken to the federal re-adaptation center number one, the maximum security prison.
19:21He won't be there long. While in hiding, he'd made a new friend, a glamorous Penn
19:26pal he hopes will make him immortal. And the wheels are about to be set in motion
19:33for Sean Penn's greatest and most controversial adventure yet.
19:37While El Chapo was on the run for 13 years, he was described by the U.S. Treasury Department
19:47as the most powerful and wealthy drug trafficker in the world.
19:51Forbes magazine listed his worth at a billion dollars. And the FBI claimed he was responsible
19:58for 70,000 deaths.
20:05El Chapo was a legend throughout Mexico.
20:16He was even something of a pop star, subject of many narco-corritos, folk songs glorifying his crimes.
20:23He even paid to have some written.
20:29But to El Chapo, like many criminal figures before him, he would never be truly legendary
20:35until his story played out on the silver screen.
20:39Amongst the drug dealers and the gangsters that I work with, El Chapo is somewhat of a folk
20:45hero because he stuck it to the man. So I don't think that El Chapo didn't think that he made it,
20:51but he's up against many other cartels. And he wants to be the number one cartel
20:57and the number one drug dealer. And of course he wants a film made about himself.
21:01In hiding, he could look to his late Colombian counterpart, Pablo Escobar.
21:06For Colombia during that time, when I was very young, for Pablo Escobar, he was somebody to be reckoned
21:12with. It was fear. I think many people were afraid. That kind of reputation, the lawlessness,
21:19I think the stereotype of what a Colombian was, that that's exactly what led me to the law.
21:26An immigrant is not a violent drug lord. An immigrant's not a criminal. An immigrant,
21:31especially Latinos, were not poor and uneducated and heartless human beings.
21:39El Chapo moved more drugs and a larger variety to more places in the world than Escobar.
21:46But Pablo Escobar had been portrayed in many movies and television shows,
21:51including the sprawling Colombian series, Escobar, El Patron del Mal, and most recently,
21:57the Netflix series Narcos. I spoke with a friend of mine who's one of the people whose life rights we
22:05had for Narcos, and he's involved with the DEA. And he said El Chapo saw Narcos while on the run.
22:12Obviously, these guys have access to computers and quite honestly, probably had a lot of time on his
22:19hands with half the country looking for him. In his mind, El Chapo needed to go Hollywood,
22:27and do it his way. I don't know if El Chapo wanted to be like Pablo Escobar,
22:33but I think they were probably cut from the same cloth. There's no doubt that there's a personality
22:38makeup of a cartel leader that certainly is boastful and wants attention. But there's another more
22:46practical reason for a desire to be represented as a larger-than-life figure in the media, which is this.
22:52To run a cartel requires intimidating your rivals. El Chapo doesn't have to do that. You can take my
23:01word for it. There will be many movies done of you when you're no longer with us. Pablo Escobar never
23:08worried about that. And yet, how many? He's on Netflix 24 hours a day. Look, if O.J. can get a movie,
23:14Chapo can get many movies, you know? El Chapo saw his chance when he struck up a friendship with another
23:21Mexican drug lord, a beautiful one, a make-believe one on Mexican television.
23:27La Reina del Sur is a soap opera about a drug lord's wife who, after his death,
23:36decides to follow in his footsteps and take over the family business and does so. And so,
23:42this soap opera was very novel for Mexican television because this is a soap opera where
23:46a woman was empowered. Drug trafficker Teresa Mendoza was played by a woman named Kate del Castillo,
23:54a veteran Mexican actress on the edge of 40. Kate del Castillo is a very beautiful,
24:00talented actress from Mexico City, and she started off in soap operas, which they call telenovelas.
24:09Kate is, I would maybe make a comparison to Jane Fonda because her father, Eric del Castillo,
24:19is a very, very respected, distinguished, leading man, actor from both television and film. And so,
24:27she was Mexico's version of Hollywood royalty, Hanoi Jane Mexico style. Kate had found some success in
24:34the States in films and shows like Jane the Virgin and Showtime's Weeds, playing another crime boss.
24:42But her role in La Reina del Sur made her a superstar in Mexico. The character in La Reina del Sur is
24:48a ruthless, murderous drug lord because that's just the nature of that business. People liked her
24:55character and it was a beloved character. She had also something that was very unusual for a Mexican
25:02soap opera. She had kind of torrid love affairs. She would have a one-night stands and things that,
25:07you know, in Mexico, at least on their television shows, are just kind of taboo.
25:12Hi, I'm Kate del Castillo for PETA. If you're thinking about going to a circus that uses animals,
25:19please reconsider. As a celebrity, Kate had her causes, but nothing like what she announced in 2012,
25:27the year after her show premiered. She went to her Twitter feed to announce that she trusted El Chapo
25:33more than the Mexican government. And she challenged the real-life fugitive drug lord to traffic in love.
25:39Well, having lived in Hollywood now for over 10 years, it's hard to discern when people are doing
25:46things for shock value. So perhaps she saw the moment or sees the moment because of her fame in
25:58Mexico to make a statement that would maybe rumple some feathers or get people titillated by her comment.
26:06Next thing you know, Kate heard from El Chapo's lawyers. El Chapo wanted to send her flowers.
26:15Perhaps Chapo Guzman, from watching the show, Reina del Sur, or growing up watching her on soap operas,
26:21felt that he had some nexus or connection or friendship with her.
26:24The virtual relationship blossomed with flirty, sexy texts.
26:28We'll drink tequila and champagne. I'll take care of everything so you're comfortable.
26:35I will take care of you more than I do my own eyes.
26:37I am so moved to hear that you will take care of me. No one has ever taken care of me.
26:43Thank you for being such a great person. You are so beautiful in every way.
26:48I am telling you, I feel safe for the first time in my life.
26:52My mother wants to meet you. I told her about you.
26:57Don't worry, nothing serious. Everything will be great.
27:01The Mexican government apparently has something similar to a wiretap law and they were able to
27:09tap the communications of Chapo Guzman with Kate del Castillo. And therefore,
27:15Kate's texts were caught in this back and forth between Chapo and Kate.
27:20After El Chapo's recapture in 2014, he had a proposal for Kate. Not a wedding proposal,
27:28but a business one. He wanted his life made into a movie, a Hollywood movie. And he wanted
27:35Kate del Castillo to set it up and produce it. That's when Kate was suggesting perhaps to Chapo
27:41that she could put together this dream team of Hollywood it people to put together this biopic film.
27:48Meanwhile, the man who'd broken out of prison once before was about to do it again.
27:54On July 11, 2015, in El Chapo's cell at the Maximum Security Prison, a hole appeared in the floor of
28:02the shower stall. A security camera showed El Chapo stroll casually into the stall and drop out of sight.
28:11Talk about Hollywood.
28:12El Chapo's team of engineers had spent three months in Germany studying techniques for digging
28:20a tunnel, avoiding underground water platforms. The tunnel cost a few million dollars. It had lights,
28:27ventilation, and a rail line on which a mounted motorcycle would speed him to a construction site,
28:33a mile away. Once he was able to escape, Chapo's lawyers sent a text to Kate saying he got out.
28:42And she said, yes, I know, I couldn't be happier. The escape didn't put the brakes on the movie plans.
28:49Kate found a Hollywood producer and asked him to be her partner on the project. Fernando Sulichen
28:55brought in his partner, Jose Ibanez. Both Argentinians, who are big-time players in Hollywood. They work
29:03often with director Oliver Stone. The next step was setting up a meeting with El Chapo to make things
29:10official. And this was where another Mexican actress stepped in. Yolanda Andrade is a famous
29:18television personality in Mexico. She's a very beautiful, bubbly, vivacious person. And she has
29:24girlfriends. Yolanda is very much out to the public. She has one, if not two, talk shows on Spanish
29:32television. And she's also very beloved by Mexico. Not to the level of Kate, but similar.
29:40Yolanda's father, Rolando, allegedly had connections to El Chapo's cartel. Reports say that she helped arrange
29:47the meeting. Yolanda and Kate are rebels. Yes. Perhaps rebels with a cause. Everything was set.
29:54Kate was ready to present her Hollywood dream team. But there were a couple of complications.
30:00For one, Kate represented a tequila brand called Honor. And she was looking for investors.
30:07Maybe, perhaps she thought that, you know, there would be some way to get him to invest in this
30:13business with her. Now, there are texts that the Mexican government has uncovered that talk about
30:18bring your tequila. You could go down to any corner store in Mexico and get a bottle of tequila.
30:22So that leads me to believe it could only be the tequila that she was trying to promote to let him
30:28taste it or see if there was any interest on his part. And there was an even bigger complication.
30:35Sean Penn got word of the meeting and asked to come along. As far as Kate knew, it wasn't a bad idea.
30:42He was a Hollywood player who could definitely get her El Chapo movie made.
30:46So Sean Penn goes down to Mexico with one agenda. His agenda is, let's see if we can meet this man
30:54and get his life rights and perhaps make either a documentary film or a Hollywood blockbuster. And
31:00Kate has that plan as well. But Kate perhaps has a second agenda. And the second agenda is this tequila
31:06bottle that she takes with her to this meeting. Now remember, the official story is that Sean Penn
31:12flew into the Mexican jungle to write an article for Rolling Stone magazine. But the clues to his
31:19ultimate aim may be in that lengthy, windy Rolling Stone piece. Penn writes of his mysterious connections
31:26and traveling companions in the El Chapo saga. One he called Espinoza, the owl who flies among falcons.
31:34The other, El Alto, a big man, worldly and well-connected. Espinoza is Fernando Sulichen, El Alto,
31:43Jose Ibáñez, both Oliver Stone's producers. Word on the boulevard is that Stone was ready to put up
31:53six million dollars for El Chapo's life rights. Was Sean Penn doing research to play El Chapo in an
32:01Oliver Stone film? Oliver Stone refused to comment. October 2nd, 2015.
32:13Van Nuys Airport. Sean Penn, Kate Del Castillo, and the Oliver Stone producers fly out in a leased
32:22Beechcraft Hawker business jet and set off for what would come to be known as the Bungle in the Jungle.
32:32The private jet carrying Sean Penn, Kate Del Castillo, and the Oliver Stone producers lands at an
32:39undisclosed airport in mid-Mexico. Flight records will say it's Guadalajara International. The group
32:46is then taken by minivan to a hotel. Penn will write that he's sure the DEA and Mexican government
32:52are tracking their movements. He's correct.
32:59At the hotel, the group is herded into a convoy of armored SUVs and driven an hour and a half to a
33:06smaller dirt airfield. One of the drivers is El Chapo's 29-year-old son, Alfredo. They board two
33:13small planes for a two-hour flight into the jungle of Sierra Madre. It's another exhausting 10-hour truck
33:21ride before Penn and his group arrive in a jungle clearing. And finally, there before him, the little
33:27man himself, El Chapo Guzman. Sean Penn had no idea what he was walking into. There was no way he could know
33:36what kind of temperament El Chapo could have, if he's a hothead, if he's been up for four days, if he's using
33:44his own product. He's a murderer. He's a drug dealer. He's definitely to be feared. This is the first time El Chapo
33:54has met Kate. Penn writes that he greets her like a daughter returning from college.
34:01Kate acts as Penn's translator in a seven-hour interview without notebook or tape recorder.
34:09Penn writes that El Chapo reminds him of Tony Montana, Al Pacino's character in Scarface,
34:18written by Oliver Stone. Let's cut to the chase here. The whole thing is
34:23very much through the looking glass. At the end of the day, he sat there with a fugitive drug lord
34:28for seven hours or whatever it was and didn't interview him. They sat around and, you know,
34:33drank beers and ate tacos. It may not have helped his Rolling Stone article, but I'm sure it helped him
34:39as an actor tremendously to see what his mannerisms are like, how he walks, how he talks. Seven hours of
34:46somebody I'm sure is a great study. When it's time to leave, Penn asks to take a photo to prove the
34:53meeting took place. It's his idea not to smile. Sean Penn and El Chapo make plans to meet in eight days for
35:03a more formal interview. But the authorities who had been watching make their move. As Penn and Kate wing
35:10back to Los Angeles, the Mexican military and DEA begin raids on El Chapo's strongholds in Sinaloa.
35:18El Chapo escapes with face and leg wounds.
35:24As the world closes in, El Chapo hides out in the coastal town of Los Mochis. He will not make the
35:31reunion with Sean Penn. But through text messages to Kate Del Castillo from a satellite phone, he agrees
35:38to honor his promise to give Penn an interview. Sort of. This will fall far short of El Chapo and Sean Penn's
35:46dreams. Sean Penn will submit questions, which will be translated into Spanish and read to El Chapo by one
35:54of his men. El Chapo agrees to respond to the written questions on video. This is the result.
36:09The video runs 17 minutes. Sean Penn provides the questions he apparently presumes everyone wants to
36:15ask the most powerful, wealthiest drug lord in the world. A man with one billion dollars responsible for
36:2270,000 deaths. He asks very penetrating things like, what's your attitude toward violence?
36:45Really? That's not an interview. It is definitely a scoop. He's definitely a get,
36:51but he just gets to choose what he says and there's no follow-up and there's no context.
36:55It is a pale facsimile of a proper interview. Because Sean wasn't there, they phoned it in.
37:01The guy who was asking the questions really was put in a situation where, you know,
37:07those questions, if they offend Chapo, his life would have been in peril, right? So you could tell
37:12his hesitation as he was asking them in Spanish. And Chapo would look at him.
37:25Let me rephrase that. I would have loved to, you know, to see Sean Penn sit down next to El Chapo and go,
37:32you see my movies? Huh? What do you think of Richmond High and Dead Man Walking?
37:37Maybe not Dead Man Walking. That would have been weird.
37:39In this list of questions, which again, is not an interview really, it's more like
37:46back page of the New York Times Magazine, fun Q&A with so-and-so. An interview is when you ask
37:52someone a question, they give you an answer, you come back again, and then you continue to probe
37:58somebody, right? To the degree that you feel is possible and understanding that you are a little
38:04bit captive, in a captive situation where there's probably armed gunmen all around you to make sure
38:09you don't want to be rude, you don't want to be hostile in any way, but you at the same time want
38:14to ask a question. That was not what was going on. Sean Penn submits his article to El Chapo for approval.
38:20Then he submits it to his editors, and he waits for the world to discover his journalistic triumph.
38:28On January 8, 2016, the military and police descend on El Chapo's hideout.
38:41Five of the drug lord's men are killed in the gun battle.
38:47But Shorty and one of his henchmen scramble into a tunnel hidden by a mirror. They hide in a sewer for
38:54four hours before emerging out a manhole onto a busy street. They hijack a white car at gunpoint.
39:03And when the car breaks down in a cloud of smoke, El Chapo hijacks a red SUV.
39:09On a busy highway a few miles away, he's surrounded and arrested.
39:13The soldiers keep him in a hotel room until the smoke clears. His pretty shirt is gone.
39:26The next day, Rolling Stone publishes Sean Penn's article. It admits that El Chapo was given
39:32editorial approval, but claims he requested no changes. Reaction is swift and negative.
39:40This article was 10,000 words long, but it was mainly about Sean Penn. He talked about his genitals,
39:47about flatulence, about El Chapo's fashion. It really wasn't a journalistic piece as we know it.
39:53It's definitely problematic to show an article ahead of publication to the subject of that article,
40:00and generally speaking, no self-respecting publication will do that. If you know in advance that the subject
40:06you're writing about is going to have approval over the piece before you write it, then there's a good
40:11chance you're going to be more careful and more selective about what you put in the piece.
40:15When news breaks, Sean Penn is at a Haiti benefit at a posh Beverly Hills hotel. His date is Madonna.
40:22Madonna right here, Madonna.
40:24Criticism intensifies in the days to follow, along with an allegation from a U.S. government official
40:30that the Rolling Stone article was just a protective cover-up. The source tells Fox News that Penn could
40:37have faced criminal charges in the States for trying to make a movie deal with a significant
40:42narcotics trafficker. If I put on my lawyer hat for a minute, this could be two people running away
40:50from an incident and every man for themself. And perhaps Sean was advised by his lawyer to say,
40:56look, man, you better run out and write an article of Rolling Stone about this thing so you can be
41:01protected under the First Amendment freedom of the press because the freedom of the press protects
41:05interviews like this. But if you don't do this and it was just the movie deal, they may be able to
41:10nab you for something. Within days, Penn finds a sympathetic journalist to hear his side. Charlie Rose
41:18treats the actor very gently, about as gently as Penn was with El Chapo. Penn tells him he considers his big
41:26El Chapo-approved Rolling Stone article to be a failure. When Sean said it was a failure,
41:31I understood exactly what he meant. Everybody was talking about Sean Penn interviewing El Chapo,
41:38instead of having the more important conversation of how are El Chapo's created. In the end,
41:45Sean Penn is left licking his wounds in Hollywood, working on his latest directing effort. Mexico's
41:51Attorney General has confirmed that Penn was essential in El Chapo's capture. I think Sean Penn
41:58didn't get a chance to, as he says, to get to the questions that he really wanted to ask,
42:04and I'm curious to know what those were. Kate now claims she was blindsided by Penn's plans for the
42:11Rolling Stone article and that he left her exposed and in danger. She's concerned that the Sinaloa cartel
42:19wants to punish her for the El Chapo debacle and she's under investigation by the Mexican government
42:25for her dealings with him. She's living in Los Angeles and resisting Mexican government demands to
42:33return to Mexico. And then there's El Chapo, waiting to see if he'll be extradited to a prison in the
42:45United States, where a third escape would be less likely. In prison, he complains that the barking of
42:52guard dogs and a nightlight interfere with his sleep. And for the first time, El Chapo is not allowed conjugal visits.

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