Through marriage ruled as Prince of Antioch from 1153 to 1160.
Lord of Oultrejordain from 1175
Knight in the Second Crusade. Muslin writers took him to be the chief enemy of Islam.
Imprisoned in Aleppo for 15 years.
Led the Crusader army at the battle of Mongisard which was a defeat for Saladin.
Executed by Saladin himself after the Battle of Hattin, part of the Ayyubid-Crusader War
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".
The above execution is enacted in the movie Kingdom of Heaven
Wikipedia:
https://en.wikipedia.org/wiki/Raynald_of_Châtillon
Ruling Princess of Antioch from 1130.
Her father was killed in an ambush near Mamistra in present day Turkey. His blond head was embalmed and sent as a gift to the caliph in Bagdad.
Her first husband Raymond of Poitures was killed in the Battle of Inab, was beheaded by Shirkuh, the uncle of Saladin and his head was placed in a silver box and sent to the Caliph of Bagdad as a gift.
Her second husband Raynald (whom she predeceased) was beheaded by Saladin himself!
You might say she managed to keep her head when all about her were losing theirs🙄 (apologies to Rudyard Kipling)