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Raynald's origins are obscure; Du Cange believed he was from Châtillon-sur-Marne , but according to Jean Richard, he was a son of Hervé II of Donzy, and he inherited Châtillon-sur-Loing sometime before joining the Second Crusade in 1147 . Other sources, however, say he was a second son of Henri I de Châtillon , Lord of Châtillon-sur-Loing, and wife Ermengarde de Montjay ,dame and heiress of Montjay . In the east, he entered the service of Constance of Antioch , whose first husband had died in 1149 . She married Raynald in secret in 1153 , without consulting her first cousin and liege lord, Baldwin III of Jerusalem.
In 1156 Raynald claimed that the Byzantine emperor had reneged on his promise to pay Raynald a sum of money, and vowed to attack the island of Cyprus in revenge. When the Latin Patriarch of Antioch refused to finance this expedition, Raynald had the Patriarch seized, stripped naked, covered in honey, and left in the burning sun on top of the citadel. When the Patriarch was released, he collapsed in exhaustion and agreed to finance Raynald's expedition against Cyprus. Raynald's forces attacked Cyprus, ravaging the island and pillaging its inhabitants.
The Emperor Manuel I Comnenus raised an army and began a march into Syria. Faced with a much larger and more powerful force, Raynald was forced to grovel, barefoot and shabby, before the emperor's throne for forgiveness. In 1159 Raynald was forced to pay homage to Manuel as punishment for his attack, promising to accept a Greek Patriarch in Antioch. When Manuel came to Antioch later that year to meet with Baldwin III , King of Jerusalem , Raynald was forced to lead Manuel's horse into the city. Soon after this, in 1160 , Raynald was captured by the Muslims during a plundering raid against the Syrian and Armenian peasants of the neighbourhood of Marash . He was confined at Aleppo for the next seventeen years. As the stepfather of the Empress Maria , he was ransomed by Manuel for the extraordinary sum of 120,000 gold dinars in 1176 .
He became notorious for his wanton cruelty , often having his enemies and hostages flung from its castle walls to be dashed to pieces on the rocks below.
In November 1177 , at the head of the army of the kingdom, he helped King Baldwin defeat Saladin at the Battle of Montgisard ; Saladin narrowly escaped. In 1181 the temptation of the caravans which passed by Kerak proved too strong and, in spite of a truce between Saladin and the king, Raynald began to plunder. Saladin demanded reparations from Baldwin IV, but Baldwin replied that he was unable to control his unruly vassal. As a result, war broke out between Saladin and the Latin kingdom in 1182 . In the course of the hostilities, Raynald launched ships on the Red Sea , partly for piracy, but partly as a threat against Mecca and Medina, challenging Islam in its own holy places. His pirates ravaged villages up and down the Red Sea, before being captured by the army of Al-Adil I only a few miles from Medina. Although Raynald's pirates were taken to Cairo and beheaded, Raynald himself escaped to the Moab . Saladin vowed to behead Raynald himself, and at the end of the year Saladin attacked Kerak . The siege was raised by Count Raymond III of Tripoli , and Raynald was quiet until 1186.
Later in 1186 Raynald attacked a caravan travelling between Cairo and Damascus, breaking the truce between Saladin and the Crusaders. King Guy chastised Raynald in an attempt to appease Saladin, but Raynald replied that he was lord of his own lands and that he had made no peace with Saladin. Saladin swore that Raynald would be executed if he was ever taken prisoner.
In 1187 Saladin invaded the kingdom, defeating the Crusaders at the Battle of Hattin . The battle left Saladin with many prisoners. Most prominent among these prisoners were Raynald and King Guy, both of whom Saladin ordered brought to his tent. The chronicler Imad ad-Din al-Isfahani , who was present at the scene, relates:
“ Saladin invited the king [Guy] to sit beside him, and when Arnat [Raynald] entered in his turn, he seated him next to his king and reminded him of his misdeeds. "How many times have you sworn an oath and violated it? How many times have you signed agreements you have never respected?" Raynald answered through a translator: "Kings have always acted thus. I did nothing more." During this time King Guy was gasping with thirst, his head dangling as though drunk, his face betraying great fright. Saladin spoke reassuring words to him, had cold water brought, and offered it to him. The king drank, then handed what remained to Raynald, who slaked his thirst in turn. The sultan then said to Guy: "You did not ask permission before giving him water. I am therefore not obliged to grant him mercy." After pronouncing these words, the sultan smiled, mounted his horse, and rode off, leaving the captives in terror. He supervised the return of the troops, and then came back to his tent. He ordered Raynald brought there, then advanced before him, sword in hand, and struck him between the neck and the shoulder-blade. When Raynald fell, he cut off his head and dragged the body by its feet to the king, who began to tremble. Seeing him thus upset, Saladin said to him in a reassuring tone: "This man was killed only because of his maleficence and perfidy". ”
King Guy was spared and was taken to Damascus for a time, then allowed to go free.
To the Christians of his time, Raynald was considered a martyr killed at the hands of the Muslims. However, documentary evidence tends to refute this idealized picture, giving the impression of Reynald as a freebooter and pirate who had little concern for the welfare of the Kingdom of Jerusalem. It could be argued that the successes of the Kingdom were undone in large measure by Raynald's recklessness, which had the effect of provoking needlessly the Muslim states surrounding Outremer.
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