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'''Raynald of Châtillon''' (also '''Reynald''' or '''Reginald of Chastillon''') (c. 1125 – [[July 4]] [[1187]]) was a [[knight]] who served in the [[Second Crusade]] and remained in the [[Holy Land]] after its defeat. There heHe ruled as [[Principality of Antioch|Prince of Antioch]] from [[1153]] to [[1160]].
 
[[Image:ReynaldofChatillon&PatriarchofAntioch.jpg|frame|Raynald of Chatillon tortures Patriarch Aimery of Antioch (From MS of William of Tyre's ''Historia'' and ''Old French Continuation'', painted in Acre, 13th century ''Bib. Nat. Française''.)]]
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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 [[List of Orthodox Patriarchs of Antioch|Greek Patriarch]] in Antioch. When Manuel came to Antioch later that year to meet with [[Baldwin III of Jerusalem|Baldwin III]], [[Kings of Jerusalem|King of Jerusalem]], Raynald was forced to lead Manuel's horse into the city.
 
Soon after this, in [[1160]], Raynald was captured by the [[Muslim]]s during a plundering raid against the [[Syria]]n and [[Armenia]]n peasants of the neighbourhood of [[Marash]]. He was confined at [[Aleppo]] for the next seventeen years. As the stepfather of the Empress [[Maria of Antioch|Maria]], he was ransomed by Manuel for the extraordinary sum of 120,000 gold dinars in [[1176]]. He served as [[Baldwin IV of Jerusalem|Baldwin IV]]'s envoy to Manuel, and, because his wife Constance had died in [[1163]], was rewarded with marriage to another wealthy widow, [[Stephanie of Milly|Stephanie]], the widow of both [[Humphrey III of Toron]] and [[Miles of Plancy]], and the heiress of the [[lordship of Oultrejordain]], including the castles [[Kerak]] and [[Montreal (Crusader castle)|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]]. He became notorious for his wanton cruelty at [[Kerak]], often having his enemies and hostages flung from theits castle walls of castle to be dashed to pieces on the rocks below.
 
In November [[1177]], at the head of the army of the [[Kingdom of Jerusalem|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 could only replyreplied that he was unable to coercecontrol his unruly vassal. The result wasAs a newresult, outbreakwar ofbroke warout 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 [[Siege of Kerak|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 Raynald was quiet until [[1186]].
 
That year he allied with [[Sibylla of Jerusalem|Sibylla]] and [[Guy of Lusignan]] against Count Raymond, and his influence contributed to the recognition of Guy as king of Jerusalem, although Raymond and the Ibelins were attempting to advance the claim of his stepson Humphrey's wife Princess Isabella. Humphrey remained loyal to his stepfather and Guy.