Attempted assassination of Augusto Pinochet

An assassination attempt was made on Chilean dictator Augusto Pinochet on 7 September 1986, when members of the urban guerrilla group Manuel Rodríguez Patriotic Front ambushed a motorcade carrying the dictator to Santiago.

Planning
The Manuel Rodríguez Patriotic Front considered 1986 to be the decisive year in their struggle against Pinochet. The guerrillas termed the assault Operation 20th Century (Operación Siglo XX). According to Patricio Manns, the attack was partially planned in Switzerland and at his house in Paris, where he lived in exile. Bulletproof vests for the operation were reportedly donated by conscripts in Sweden and Switzerland.

The location of the attack, Cuesta de Las Achupallas, was carefully selected by the guerillas. Cuesta de Las Achupallas is a bottleneck road along mountainous terrain between Santiago and Cajón del Maipo. The guerrillas rented a house in the vicinity, posing as seminary students. The plan involved using a heavy vehicle to block the motorcade's advance.

The death of former President Jorge Alessandri on August 31 influenced events by requiring Pinochet to travel back to Santiago, which changed the schedule of the attack.

Ambush
When Pinochet's motorcade arrived at the selected area at 18:35, it came under heavy fire. The guerrillas had 17 rifles; all of them, except one, were M16 rifles. They also had 10 M72 LAW rocket-propelled grenade launchers, one submachine gun, and an "unknown number" of homemade grenades. The local mountainous geography prevented Pinochet's guards from using radio communication with nearby military and police units. However, despite being on a narrow road next to a ravine, Pinochet's car managed to turn around and escape the scene, albeit not before being hit by a rocket-propelled grenade. The grenade fired at Pinochet's car did not, however, explode upon impact. Though Pinochet was unhurt, the shots killed five soldiers and injured eleven others. Initially, the guerrillas thought they had killed Pinochet and escaped the scene by pretending to be part of the security staff to evade incoming military and police.

Aftermath
The assassination attempt triggered a wave of repression against dissidents of the dictatorship. Opposition figures unrelated to the events, such as Ricardo Lagos, Patricio Hales, and Germán Correa, were arrested, and journalist José Carrasco, who was already in custody, was killed. The failure of Pinochet's attempted assassination led to an internal crisis in the Manuel Rodríguez Patriotic Front, resulting in splits and the complete autonomy of the group from the Communist Party by 1987. The attackers faced different fates, but many were hunted down either in October 1986 or in the years leading up to the Chilean transition to democracy in 1990. José Joaquín Valenzuela, who was the "operative leader" of the attack, was extrajudicially killed in Operación Albania. Some of the people involved in the attack ended up in prison from which they escaped through a tunnel in 1990.