On the evening of 7 September 1986, members of the urban guerrilla group Manuel Rodríguez Patriotic Front (, FPMR) ambushed Chilean dictator Augusto Pinochet's motorcade on a mountain road in Cajón del Maipo, southeast of Santiago. The FPMR code-named the operation Operation Twentieth Century (). Roughly twenty fighters struck the five-car convoy as Pinochet returned from his country residence at El Melocotón, and the attackers, armed with automatic rifles and M72 LAW anti-tank rocket launchers, killed five of Pinochet's bodyguards and wounded at least eleven more. Pinochet himself escaped with only minor cuts after his driver reversed the armored Mercedes-Benz out of the kill zone.
It was the only serious attempt on Pinochet's life during his seventeen years in power. In its aftermath, Pinochet declared a 90-day state of siege, and security forces carried out a wave of arrests and extrajudicial killings, including the murder of journalist José Carrasco Tapia. The operation's failure triggered a leadership crisis within the FPMR that led it to break definitively from the Communist Party of Chile within a year. Several of the attack's organizers were later killed by state security agents or imprisoned. Some of those imprisoned were later involved in a mass tunnel escape from Santiago's Cárcel Pública in January 1990, and, in December 1996, commander Mauricio Hernández Norambuena escaped from a maximum-security prison by helicopter.
Background By late 1985 the FPMR's national leadership had concluded that 1986 would be the decisive year in its armed campaign against the dictatorship, and tasked José Joaquín Valenzuela Levi — known within the organization as "Commander Ernesto" — with planning an operation to kill Pinochet. The plan, eventually code-named Operation Twentieth Century (and referred to internally as "Operación Patria Nueva"), reportedly originated in late 1984, when the FPMR's leadership began discussing the idea of killing Pinochet and assigned the initial reconnaissance to militant Rodrigo Rodríguez Otero, before the operation was given final form and approved in 1985.
Valenzuela Levi, who had studied in East Germany and received guerrilla training in Bulgaria and Cuba, led the operation's planning together with Cecilia Magni, known as "Commander Tamara"; Magni organized much of the logistics but, at leadership's insistence, did not take part in the ambush itself. According to Patricio Manns, parts of the plan were worked out in Switzerland and at his home in exile in Paris, and bulletproof vests used by the attackers were reportedly donated by conscripts in Sweden and Switzerland. Two Cuban defectors later told the CIA that the assault team received preparation in Cuba, where the operation was planned in detail, and that a unit of Cuban special forces landed weapons for the attack on a remote stretch of Chile's northern coast from a vessel of the Cuban fishing fleet. A month before the ambush, Chilean police had discovered a large cache of Cuban-supplied weapons hidden at Carrizal Bajo on the coast of the Atacama Region, an operation that had served for months as a route for smuggling heavy weapons into the country; some of the same class of arms was to have been used against Pinochet, although the attackers ultimately fired U.S.-made M72 LAW launchers rather than the Soviet-designed RPG-7s for which they had trained.
Seventeen FPMR militants took part in the operation, several of whom had received military instruction from Cuban special-forces officers, including Lázaro Betancourt, who later said he had helped train some of the attackers.
Planning and preparation Pinochet regularly spent weekends at his country home in El Melocotón, in the Cajón del Maipo roughly 30 miles (48 km) southeast of Santiago, traveling with a military escort commanded by Army Captain Juan Mac Lean Vergara. The FPMR determined that the ambush would take place on Pinochet's Sunday return journey to the capital. Planners initially considered detonating explosives on the highway near the Las Vizcachas motor-racing circuit but abandoned the idea after concluding that the convoy's speed at that point made it impossible to guarantee which car in the column carried Pinochet, since his security detail deliberately varied his position among several look-alike Mercedes-Benz sedans.
The group instead settled on an ambush along the Cuesta de Las Achupallas, a narrow, winding stretch of road between the settlements of La Obra and Las Vertientes. The site was chosen deliberately: a low hill on the road's northern side offered the attackers a firing position, while a roughly 20-meter (66-foot) ravine on the southern side would make it difficult for Pinochet's escort to maneuver, take cover, or return fire effectively; the surrounding mountains were also known to disrupt radio communication with nearby police and military units. Militants César Bunster and Cecilia Magni arranged for the vehicles used in the operation and rented a house nearby in the sector of La Obra, where the assault team assembled. More broadly, the guerrillas rented a house in the area and, posing as seminary students, hid there for five days before the attack, reportedly receiving additional training from an army officer sympathetic to their cause.
The attack was originally scheduled for Sunday, 31 August 1986, but the death that weekend of former president Jorge Alessandri forced Pinochet to return to Santiago overnight, upsetting the plan. The attackers, still posing as seminarians, relocated to the nearby town of San Alfonso and waited a further week for Pinochet's next scheduled trip.
The ambush Forces involved On the afternoon of 7 September 1986, Pinochet's convoy left El Melocotón for Santiago at around 18:00. According to a later reconstruction by the Chilean newspaper La Tercera, it consisted of two motorcycle outriders from the Carabineros and five cars carrying a total of 21 people, trailed at a distance by two additional vehicles of the National Information Center (CNI). Pinochet rode in the fourth car, an armored Mercedes-Benz, accompanied by his ten-year-old grandson, Rodrigo García, his naval aide Captain Pedro Arrieta, and his driver, Army Corporal Óscar Carvajal. The boy had reportedly asked to ride in one of the escort cars, but Pinochet's wife, Lucía Hiriart, insisted he travel with his grandfather — a decision that placed him in the best-protected vehicle in the column.
The FPMR fielded roughly seventeen rifles, sixteen of them automatic M16 rifles, along with a SIG Sauer rifle, a P25 submachine gun, ten M72 LAW rocket launchers, and an unspecified number of homemade hand grenades. The attack team, estimated by authorities at between twelve and forty fighters, organized itself into small units: one group blocked the road with a car towing a camping trailer; two more took up firing positions on the hillside overlooking the road; and a fourth, in an off-road vehicle, was positioned further down the route to prevent any car from escaping the ambush.
Attack At 18:35, as the convoy reached the Cuesta de Las Achupallas, the blocking vehicle swerved across the road behind the two motorcycle outriders, and the attackers opened fire. "Intense firing began," Pinochet later recalled, "with machine guns, rifles and bazookas or possibly rocket launchers and some hand grenades." The barrage, coming from both the roadblock and the surrounding hillsides, immediately cut down the motorcycle escort, and a rocket struck the second car in the column, setting it ablaze. The lead vehicle, carrying four Carabineros, was raked with automatic fire and struck by a rocket that failed to detonate properly; its driver was killed almost immediately, leaving the car stranded in the line of fire, though according to the attackers' own account two of its occupants continued returning fire despite being wounded.
Pinochet's driver, recognizing that the armored Mercedes had entered the kill zone, reversed the car, executed a U-turn, and sped back toward El Melocotón to raise the alarm, since the mountainous terrain prevented radio contact with outside units. An M72 rocket reportedly struck the car during the maneuver but failed to penetrate its armor, allowing Pinochet, his grandson, and his aide to escape largely unharmed. "My first reaction was to get out of the car," Pinochet told reporters hours later, "but then I thought of my grandson at my side and I covered his body with mine. ... I never believed I would come out alive."
With Pinochet's car gone, the attackers concentrated fire on the remaining vehicles. A rocket struck the third car, carrying part of Mac Lean's civilian-clothed escort, killing one occupant outright and wounding several others as they abandoned the burning vehicle; some survivors threw themselves into the ravine beside the road to escape the gunfire from the hillside. The rearmost car, carrying four army commandos who formed the convoy's final layer of protection, was destroyed by rocket fire after its occupants dismounted to fight; several were killed or wounded in the exchange, and, as with the third vehicle's crew, some survivors escaped by climbing down into the ravine once their ammunition was exhausted. Pinochet's physician, riding in a separate car, was not seriously engaged.
The gun battle lasted roughly six minutes. Convinced they had killed Pinochet, the attackers withdrew down the canyon, mounting flashing lights and sirens on their vehicles so that arriving reinforcements mistook them for CNI units, allowing them to slip through the police cordon and disperse into safe houses in Santiago. The car in which Pinochet had ridden was later displayed publicly in Santiago bearing 38 bullet strikes, none of which had penetrated its armor plating.
Casualties Five members of Pinochet's escort were killed and at least eleven others wounded, in addition to the minor cuts Pinochet sustained to his hand from flying debris. Three civilians who happened to be on the road were also reported wounded by gunfire or shrapnel, and a police detective was injured after falling into the ravine while attempting to help the wounded. None of the attackers were killed or captured during the ambush itself.
Aftermath Repression Hours after the attack, Pinochet declared a 90-day state of siege, suspending civil liberties and granting the government broad powers of censorship and detention. Chilean television broadcast coded messages that night, disguised as public-service announcements, summoning members of specialist military units to their barracks. Security forces arrested opposition figures with no connection to the ambush, including Patricio Hales, who was detained at his home under the state-of-siege decree, and Germán Correa, and raided leftist neighborhoods in Santiago in a hunt for suspects. Ricardo Lagos, later President of Chile, was reportedly included on the CNI's list of targets that night; he survived only because Carabineros had already detained him hours earlier, so the CNI squad sent to his home found him already in police custody.
That same night, CNI agents separately abducted four government opponents with no connection to the ambush from their own homes and killed each of them in reprisal, dumping their bodies at different points around Santiago; the victims were pre-selected because of their known left-wing affiliations, and included journalist José Carrasco Tapia, an editor at the magazine Análisis and a member of the Revolutionary Left Movement, who was seized from his home; artist Gastón Vidaurrázaga Manríquez, advertising executive Abraham Muskatblit Eidelstein, and electrician Felipe Rivera Fajardo were killed alongside him. In 2007, a Chilean appeals court convicted fourteen former CNI agents over the killings, sentencing the unit's operations chief, Álvaro Corbalán, to 18 years in prison, with other defendants receiving terms of five to thirteen years.