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The Siege of Kerak took place in 1183 between the Crusader Kingdom of Jerusalem and Saladin at Kerak Castle, stronghold of Raynald of Chatillon.

Raynald was Lord of Oultrejordain, one of the major baronies of the kingdom, mostly consisting of land to the east of the Jordan River and centred around the castles of Kerak and Montreal. Raynald considered himself a petty king and often refused to obey the truce made between Saladin and Jerusalem. In 1183 he organized a raid on the Red Sea, capturing Eilat and threatening to sail against Mecca, Islam's holiest city. Raynald's fleet was subsequently captured and its men executed by Saladin's brother Al-Adil and an Egyptian fleet.

Saladin was outraged and demanded vengeance. He invaded the northern part of the kingdom, and Guy of Lusignan, brother-in-law of King Baldwin IV, was sent out to meet him. Neither side could dislodge the other's position, and Saladin eventually withdrew, but Guy's hesitation, considered a sign of weakness, and his support for Raynald's brazen attempts to provoke Saladin caused Baldwin, who was suffering from leprosy, to depose him from the regency of the kingdom. Raymond III of Tripoli took over as regent, along with his allies among the nobility.

Meanwhile, Raynald, an ally of Guy and an enemy of Raymond and the noble faction, was organizing the marriage of Humphrey IV of Toron and Isabella of Jerusalem at Kerak. Sixteen-year-old Humphrey was Raynald's step-son and heir to Oultrejordain; Isabella, only eleven years old, was Baldwin IV's step-sister. The marriage took place in November of 1183 and the festivities were luxurious, but Saladin took the opportunity to march south and besiege the castle with troops from both Damascus and Egypt.

The marriage continued while Saladin attacked the walls with nine mangonels. Both sides were already very familiar with each other through years of conflict and peace, and the siege was almost a friendly event. Humphrey's mother Stephanie of Milly sent some of the wedding feast to Saladin, and the sultan, who had no quarrel with anyone but Raynald, agreed not to target the wedding chamber of Humphrey and Isabella. Still, capturing the massive fortress from his greatest enemy was Saladin's ultimate goal, and messengers were sent from Kerak to seek help from King Baldwin.

Although Baldwin was by now so diseased that he could no longer walk, he insisted on leading the relief force personally. Raymond III accompanied him, and the appearance of the royal army was all it took to convince Saladin to give up his siege, which was in any case ineffectual against the heavily fortified castle. Baldwin was received triumphantly in Kerak; the king had once again defeated Saladin, despite his leprosy, just as he had done at the Battle of Montgisard in 1177. Such personal strength and courage was quite impressive to the medieval mind, for which a leper was usually a social outcast.

Saladin besieged Kerak again in 1184 with reinforcements from the Ortoqids, but was again unsuccessful. In 1185 Baldwin IV finally succumbed to his disease, and the kingdom passed to his nephew, the child Baldwin V. Baldwin V too soon died, and a succession crisis erupted between the supporters of Raymond III among the nobility on the one hand, and the supporters of Guy of Lusignan among the royal family on the other. Saladin seized this opportunity to invade the kingdom, and inflicted a devastating defeat on the Christians at the Battle of Hattin in 1187.

A largely fictionalized Siege of Kerak was depicted in the 2005 movie Kingdom of Heaven.