The movie begins with a video being shot of men tied with their hands behind their back. An enforcer, who we learn later is Lado (Benicio Del Toro) wears a skull Lucha libre mask and runs a chainsaw.
O (named after Ophelia, played by Blake Lively) narrates. The love of her life is two men, Ben (Aaron Johnson) and Chon (Taylor Kitsch). To her, Ben is like warm wood, the idealistic “Buddhist,” and Chon is steel, the “baddist.” The three have a polyamorous relationship and live together in Laguna Beach in a luxurious cliff-side house for which Ben paid with cash. Ben and Chon are high school buddies. Ben went to Berkeley and majored in business and botany. Chon was a Navy Seal with tours in Iraq and Afghanistan. One day, lounging on the beach, Ben asks Chon where you can get the best weed. Chon replies Afghanistan, and during a tour there, smuggles out marijuana seeds from which Ben grew in a greenhouse, using his scientific knowledge, cannabis with a THC yield of 33%, the best in the world. They met O when they hired her to help with managing the greenhouse. Ben is the businessman who runs the production and distribution and handles 99% of the business, while Chon handles the 1% (enforcement). Ben's philosophy is to provide what people want, but Chon is the realist in seeing the money made from marijuana. They sell to marijuana clubs and dispensaries, but most of the money is made from selling on the street, which is $6000 a pound.
After making love to O, Chon sees on his computer an email. The email has a video of Lado kicking around the decapitated heads and reads, “You guys were stupid. It's time to talk.” O and Chon greet Ben returning from a volunteerism trip to Africa. Chon and Ben discuss the business. Ben wants to give up the business to the Mexican cartel as he wants to go into philanthropic ventures such as making $10 solar panels. But Chon argues that selling would show weakness.
We see Lado and his “gardening crew” carry out a hit. Lado accosts a middleman in his home. The middleman pleads forgiveness and promises an even better deal than paying up. He calls El Azul (Joaquin Cosio), a cartel head honcho, to connect him with Lado, but Lado shoots the middleman and has a teenage cartel-member-in-training shoot the middleman's wife, while El Azul is on the phone, enraging him. The gardening crew smuggles the bodies out of the house in trash bins. We learn that El Azul is a former inside man with the Baja cartel, the cartel Lado works for. The head of the Baja cartel, Elena (Selma Hayek), had a falling-out with El Azul, and now El Azul is encroaching on the Baja cartel's territory, threatening to take over her position.
Ben and Chon meet with Dennis (John Travolta), a DEA agent on Ben and Chon's payroll. Dennis tells them about the Baja cartel: they want Ben and Chon's market to fill a market they don't have. Dennis urges them to take the deal instead of decapitation. Dennis is sympathetic to them because his wife has cancer and Ben provides him with his cannabis to ease the chemotherapy.
Ben and Chon go to a hotel room and meet with Alex (Demian Bichir), the representative for Elena. The meeting is secretly video-recorded by Lado, with the video feed shown to Elena in her Tijuana compound.
Alex lays out the deal: three years of working together, during which the cartel will learn Ben's horticulture methods while providing vast distribution networks and the operation in a safe haven on an Indian reservation that the cartel owns. (The Indian reservations are considered out of U.S. jurisdiction.) During the meeting, Chon badmouths the cartel's products. Ben and Chon step out onto the balcony to discuss. We see a formidable security apparatus, a team of Chon's ex-Navy Seal friends, who have sniper wares trained on the hotel room, backing them. Ben and Chon reach a decision. They will give the cartel their business but not join them. The cartel is not happy.
Fearing the consequences of their decision, Ben meets with his money guy, Spin (Emile Hirsch), an ex-Goldman Sachs banker who launders and invests the marijuana company's money. Ben wants to set up funds to disappear for three years in Indonesia. Ben, Chon, and O have dinner and discuss the plan for their new lives. Unbeknownst to them, they are being watched in the restaurant by Lado's crew. The three celebrate by getting high in their beach house and having a threesome. Lado sits in the car, spying on them. He calls Elena to update the situation. Elena says she needs Ben and Chon to join her for their expertise. Hearing about their living situation, she found their weakness: O.
The three prepare to leave for Indonesia. O wants to do a last shopping trip and Chon assigns someone from the security team for her. O is driving to South Coast Plaza (an upscale mall in Orange County), but one of Lado's men intercepts the bodyguard and kills him. They tail O. In one scene, O is shopping next to a girl on a cellphone, answering her mom's questions about college life. Her mom turns out to be Elena.
Returning home but not finding O, Ben and Chon hear a chime indicating a Skype call, and to their horror, see a feed of the kidnapped O. Elena, her voice masked, reprimands the boys for not complying with the deal. To redress the insult of the cartel's product during the meeting, Elena has Chon put a gun into his mouth, indicating she will tell Lado to cut off O's fingers otherwise. She almost gets Chon to pull the trigger but stops him at the last minute, telling him this will clean up his mouth.
Elena tells Ben and Chon to deliver 300 pounds of their marijuana in five hours to show compliance. They get the product and race to Chula Vista. They arrive just in time despite being almost pulled over (and Chon having to kill the highway patrolman). Lado and his men take their car. Ben and Chon drive back in Lado's truck but inside the truck are the suitcase of money and a cell phone. Elena calls, her voice unmasked, and tells them that she will hold O hostage for one year. Chon argues with Ben that they have to fight to get O back -- the cartel members are savages who will kill them. But Ben just wants peace and O back.
Ben and Chon meet again with Dennis, who tells them about the conflict between Elena and El Azul. Chon strong-arms Dennis into getting data on Elena and the Baja cartel from the DEA. He is able to get 60 days of financial transactions, encoded onto two credit cards. Back in their company HQ, Ben and Chon have Spin and his experts look into the financial data on the computer. From it, they trace Elena's financial routes. They figure out that one of her real-estate holdings, a trailer house, is a drop off point for the cartel's business. Ben decides on a plan to pay to get O back. He and Elena negotiate to a $13 million ransom. They decide to hijack the drop to get the cash for O's ransom, and make it look like El Azul hit the cartel.
The hijacking goes underway. Wearing masks, Chon and his team of ex-Navy Seals blow up the front car in a convoy with IEDs. When the men from the trailer retaliate, an ex-Navy Seal member takes them out with an RPG. Chon forces the men out of the car carrying the cash by putting a grenade in the gas tank. He takes the briefcase from a man scrambling out of the car. Ben is horrified by the killings. One of the cartel members is about to shoot Ben, but Chon shoots the member in the back, spraying blood on Ben's mask. They take the money and get away. Alex and Lado arrive to assess the damage, which is 3 million dollars gone and seven men dead. Lado urges Alex not to inform Elena of the lost because he wants to recover the money and rectify the situation himself because he fears Elena.
Ben and Chon get a message to have Ben meet with Alex and Lado. Alex and Lado interrogate Ben to find out their whereabouts during the hijacking but Ben plays it cool. He insinuates that it could be Lado's men. After Ben leaves, Alex decides Ben and Chon don't have the balls for the attack. He suspects El Azul but Lado isn't so sure.
We see O at the shack where they are holding her. She is being watched over by the teenage cartel-member-in-training. Her living conditions are bad: one of her legs is chained to a chair, she has a bucket for a bathroom and sleeps on a spring bed in a cage. She pleads into the surveillance camera and gets to talk to Elena, and begs her for marijuana. Later we see Lado giving drugs to O and O getting high. Afterwards, he tells the teenager, don't look at me like that (because we see later in the movie Lado shows O a cellphone video of him raping her while she was high).
Elena is on the phone, telling her daughter, Magda (Sandra Echevarria), that she is coming to California to visit. She gets on a private plane to the Indian reservation (to avoid U.S. customs). But before boarding the plane, Lado shoots the teenage-cartel-member-in-training, saying that he's too sensitive to handle the work. Upon arrival, Lado brings O to Elena. Elena busts Lado about the hijacking, slapping his face. She threatens Lado to recover the money. At a posh spa, Elena and O have dinner during which we learn that Elena inherited the business after her husband was killed. Her sons and brothers were also killed, and only her daughter is still alive. Elena asks O how long O has been using. Since 8th grade, O says, not that her mother cared. Elena remarks to O that the two men must love each other more than O because otherwise, they wouldn't share her.
Ben has Spin fabricate documents and hack into Alex's bank accounts to frame Alex as the mole to El Azul. Ben confronts Lado with Alex's dossier. Later, Lado brings Ben and Chon to see Alex being whipped. The torture is video-fed to Elena who forces O to watch. Under the threat of his family being harmed, Alex confesses to working with El Azul. He begs Elena for forgiveness and during the exchange Ben realizes that Elena let slip that she has a daughter in the U.S. Lado douses Alex with gasoline and anoints Ben to be the executioner. To go through with the falsehood, Ben ignites Alex. O watches in horror.
Ben and Chon make a plan that will work even faster than accumulating the money for ransom: kidnap Elena's daughter and trade her for O. To save himself, Lado visits El Azul and makes a deal to work with him. Lado pays Dennis a visit at his home. It turns out Lado also has Dennis on the payroll. Under threat, Dennis reveals that the hijackers are Ben and Chon, but that they are going to give the $3 million to Elena and not Lado. (Lado knows it's not El Azul because Lado is working with El Azul.) To head off Elena, Lado also wants to kidnap Magda. Dennis is incredulous to learn that Elena is on U.S. soil.
Dennis meets with Ben and Chon, anticipates that they want to kidnap Magda, and gives them her address. They kidnap her (after killing her bodyguard) in her dorm. Wearing masks as a show, they Skype with Elena and show a shivering Magda stuffed in an ice box (with her dead bodyguard). Elena meekly agrees to their demands.
Elena's SUV and Ben and Chon's SUV meet in an open field. On the mountain ridges, each group has their sniper team in position. Elena steps into the open with O. O runs to Ben. Ben and Chon release Magda to Elena. But before Elena returns to her car, she asks Chon who the rat is (who revealed Madga's address). Chon blows Lado a kiss. Elena turns around to shoot Lado, but Lado draws the gun on her first. As Elena lies dying, she tells Ben and Chon to make sure Magda is safe.
A shootout is underway. Each group's sniper team shoots at each other, taking out some members of each team. Chon kills Elena's bodyguards and Ben and Chon converge on Lado, hiding behind the SUV. Ben shoots Lado in the back, but Lado turns around to shoot Ben in the throat. Lado sprawls on the ground. O gets a gun and shoots Lado dead in vindication. O rushes to Ben. As O cradles Ben, Chon pulls out a syringe and stabs Ben, O, and then himself. They die in a triple suicide. That's the perfect ending, O narrates while looking into the sky.
But wait. Rewind. What really happened as O narrates, is more of a f*up than a shootout. After Elena steps out into the open and releases O, Lado retreats to the car and drives away. A helicopter and DEA agents swoop in to arrest Elena. The DEA agents disarm the sniper teams and arrest everyone (including Ben, Chon, and O).
O narrates as we see a montage: Dennis is grandstanding on TV about Elena's arrest and the progress on the war on drugs (Indian grounds are still U.S. grounds he says); Ben and Chon are released after Dennis said that they were the confidential informants; Lado and El Azul form a new cartel to take over the vacuum left by Elena.
In the end, Ben, Chon, and O couldn't go back to their old ways. Maybe it is true that there can't be equal love among three people, O says. O is shown living abroad without Ben and Chon. Ben is shown doing volunteer work in Africa, and Chon is living in the U.S. She narrates maybe one day she'll be reunited with them.
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