Saladin was the target of several assassination attempts in the 1170s when he was trying to subdue Syria. The assassins (hashashins) belonging to the sect run by the fearsome Iraqi leader Rashid al-Din Sinan, popularly known as the Old Man of the Mountain, came close to killing Saladin on at least two occasions. In the last three decades of the twelfth century, Sinan’s sect was an unpredictable and formidable player in the politics of the Levant—their assassins often proved as effective as a military force.
William of Tyre, twelfth century chronicler, believed that Sinan commanded absolute loyalty from his men. In his Chronicle on Jerusalem, William of Tyre wrote, “they [Sinan’s followers] regard nothing as too harsh or difficult and eagerly undertake even the most dangerous tasks at his command.” Saladin was forced to delay his Syrian conquests by several years because of the threat that he faced from Sinan’s assassins.
In early 1175, when Saladin’s army laid siege to Aleppo, a group of thirteen assassins managed to enter the inner circle of his camp. One of these assassins forced his way into Saladin’s sleeping quarter. He tried to strike Saladin with a knife while he was in his bed, but the royal bodyguards managed to cut him down. The assassination attempt was foiled. In May 1176, the assassins struck again. This time one of the assassins managed to strike Saladin on his chest with his sword. But Saladin was saved by the armor that he was wearing. From this time, Saladin did not allow anyone in his presence whom he did not personally recognize.
In August 1176, Saladin decided to wipe out the assassin sect. He laid siege to the assassin castle in Masyaf. But in less than a week, he broke off the siege and retreated to Huma. The chroniclers of that period assert that Saladin decided to lift the siege because the assassin sect had threatened an unrelenting campaign against him and his Abbasid clan.
In his book The Assassins: A Radical Sect in Islam, Bernard Lewis quotes a twelfth century source which gives a chilling explanation for Saladin’s decision to lift the siege. While the siege was on, an envoy of Sinan arrived to negotiate. The envoy was searched for weapons and then brought before Saladin. The envoy insisted that he wanted to talk to the Sultan in private. Saladin dismissed everyone except two of his most trusted guards whom he regarded as his sons. Here’s an excerpt from the passage that Lewis quotes from the ancient source:
“The envoy then turned to the pair of guards and said: “If I ordered you in the name of my master to kill this sultan, would you do so?” They answered yes, and drew their swords saying: “Command us as you wish.” Saladin was astounded, and the messenger left, taking the two guards with him. And thereafter Saladin inclined to make peace with him [Sinan].”
Conrad of Montserrat, Italian nobleman who was a major participant in the Third Crusade, was assassinated in Tyre, a crusader held city, on April 28, 1192, by two assassins belonging to Sinan’s sect. One of the two assassins was caught by the crusaders, and under intense interrogation he confessed that Richard Lionheart of England had paid Sinan to get Conrad assassinated. But this accusation against Richard is impossible to prove.