Raynald of Châtillon

The second son of a French noble family, Raynald joined the Second Crusade in 1147 and stayed in Jerusalem as a mercenary. Six years later he married Princess Constance of Antioch, a match her subjects saw as beneath her, and ruled as Prince of Antioch from 1153 to 1160 or 1161. Always short of cash, he tortured the Latin Patriarch of Antioch for refusing a subsidy, then launched a plundering raid in Cyprus that brought Byzantine emperor Manuel I Komnenos down on him with an army. Captured raiding the Euphrates valley around 1160, he spent sixteen years in a Muslim prison. Released in 1176, he found his wife dead and married Stephanie of Milly, the heiress of Transjordan, becoming one of the kingdom's richest barons. As regent in 1177, he led the crusader force that beat Saladin at Montgisard, then spent the next decade raiding caravans along the Egypt-Syria route - including a 1183 fleet raid on the Red Sea that threatened the pilgrim road to Mecca. His seizure of a caravan in late 1186 or early 1187, in defiance of a truce, gave Saladin the opening to invade. At Hattin, Saladin took him alive and beheaded him personally after he refused conversion.