Raynald of Châtillon (also Reynald or Reginald of Chastillon) (died July 4, 1187) was a knight who served in the Second Crusade and remained in the Holy Land after its defeat. There he ruled as Prince of Antioch from 1153 to 1160.
He was a younger son of Henry, lord of Châtillon, from a middle-ranking French noble family.
Raynald entered into the service of Constance of Antioch and was chosen to be her husband in 1153, four years after the death of her first husband, Raymund. One of Raynald's first acts in Antioch was an assault on the Latin Patriarch; two years later he attacked Cyprus, ravaging the island. Cyprus was a possession of the Byzantine Empire, and in 1159 Raynald was forced to pay homage to Byzantine emperor Manuel I Comnenus 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. After his released in 1176, he married Stephanie, the widow of Humphrey III of Toron, and the heiress of the castles Kerak and Montreal to the southeast of the Dead Sea. These fortresses controlled the trade routes between Egypt and Damascus and gave Raynald access to the Red Sea.
In November 1177, at the head of the army of the kingdom, he defeated 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 Baldwin IV, Raynald began to plunder. Saladin demanded reparations from Baldwin IV, but Baldwin could only reply that he was unable to coerce his unruly vassal. The result was a new outbreak of war 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 party as a threat against Mecca, challenging Islam in its own holy place. His ships were captured by one of Saladin's officers, and at the end of the year Saladin attacked Kerak, during the marriage of Raynald's stepson Humphrey IV of Toron to Isabella of Jerusalem. The siege was raised by Count Raymond III of Tripoli, and Reynald was quiet until 1186.
That year he allied with Sibylla and Guy of Lusignan against Count Raymond, and his influence contributed to the recognition of Guy as king of Jerusalem, although Raymond was the better candidate. Later in 1186 Raynald attacked a caravan in which Saladin's sister was travelling, 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 Reynald and King Guy, both of whom Saladin ordered brought to his tent. After being rebuked by Saladin for his treachery, Raynauld was executed. According to different accounts Saladin either personally beheaded Raynauld or ordered him to be killed in the presence of his companions. King Guy, however, was spared. Saladin explained that one king did not kill another and that Raynauld had only been executed because of his great crimes. Guy was taken to Damascus for a time, then allowed to go free.
Many of the Crusaders considered Raynald a martyr, although all evidence shows him to have been a plunderer and a pirate who had little concern for the welfare of the Kingdom. The successes of the Kingdom were almost singlehandedly undone by Raynald's recklessness and selfishness.
Reynald and Constance had two daughters: Agnes, who married king Bela III of Hungary; and Alix, who married Azzo V d'Este.