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In the epic Mahābhārata, Jayadratha (Sanskrit: जयद्रथ) was the king of Sindhu Kingdom (so he is also called as Saindhava). He was married to Dushala, the only sister of the 100 Kaurava brothers. He was the son of the king Vridhakshtra.
Abduction of Draupadi
One day, during the time the Pandavas were in exile, the Pandavas need to gather samitha and darbha (holy grass) for rituals and to gather food. They left Draupadi alone at the ashrama and request Sage Trunabindu to watch over her. On that day Jayadratha sees Draupadi, he sends his minister Kotikasya and asks him to inquire as to who she was. Kotikasya goes to her and after learning about her identity, informs Jayadratha that she is Draupadi, the wife of the Pandavas. Jayadratha in spite of learning her identity, goes to Draupadi and proposes to marry her. Initially welcoming him as their brother-in-law, Draupadi vehemently refuses the proposal. Infuriated, Jayadratha abducts Draupadi and starts moving towards his kingdom. The Pandavas who return to their ashrama and find Draupadi missing, learn about the event that has unfolded by the account of Draupadi's friend Dhaatreyika, who witnesses Jayadratha forcefully carrying Draupadi. Yudhisthira then orders Arjuna and Bhima to rescue Draupadi. Both of them defeat Jayadratha and bring him before Yudhisthira. Draupadi begs for Jayadratha to be pardoned and not killed, in order to prevent Dushala from becoming a widow. She suggests he be treated like a slave. So, Bhima shaves Jayadratha's head leaving him with just five spots of hair on his head, before setting him free. 
The first boon from Shiva
Jayadratha desires to avenge his humiliation from the Pandavas by defeating them in the battle field. So, Jayadratha performs a rigorous tapasya in order to please Lord Shiva. When Lord Shiva appears before him, Jayadratha in turn asks for the ability to defeat the Pandavas. Shiva replies that such a boon is impossible, as the Pandavas are too mighty. However, he gives Jayadratha the ability to check the advance of the Pandavas and their forces for one whole day. However, Shiva warns Jayadratha that Arjuna is an exception to this boon.
The messages of the encounter are manifold. One, that Lord Shiva is known to love all of his devotees equally and does not ignore the tapasya of anyone. Two, that God must return prayer with something. Three, that God, or any giver of boon, should only promise what is within his limits.
The second boon from his father
Years before abdicating his throne, Jayadratha's father, Vridhakshtra, hears a prophecy that his son is going to be killed. Scared for his lineage, Vridhakshtra leaves for the forest and becomes a sage. Through penance, he attempts to gain enough spiritual power to grant his son immortality or the equivalent of Bhishma's boon. However, he only manages enough to curse that whomsoever causes the head of Jayadratha to fall on the ground will be killed immediately by having his own head burst into many pieces.
In the Kurukshetra war
Naturally, Jayadratha fights on the side of Duryodhana in the Kurukshetra War. On the 13th day of the Mahabharata war, when the chakravyuha is launched by Dronacharya, Jayadratha makes use of Lord Shiva's boon. Arjuna's son Abhimanyu manages to enter the formation; he intends for the Pandava forces to follow after him and smash the formation from the inside. Jayadratha moves to close the gap, and is able to hold all the Pandava brothers and their forces at bay. As part of Drona's strategy, Arjuna and Krishna are busy battling Susharma and the Trigata Army elsewhere. Abhimanyu, who does not know how to exit from the chakravyuha, is trapped and brutally killed by the Kaurava Warriors in a combined attack.
The Pandavas are startled after finding that Jayadratha was able to hold the world's most powerful warriors at bay. In particular, Draupadi, Yudhishthira, and Bhima feel very guilty for not killing Jayadratha when they did have the chance. Arjuna blames Jayadratha to be the cause for Abhimanyu's death. He vows to kill him the very next day before sunset, failing which Arjuna would kill himself by jumping in a pyre of fire. This sets the stage for the epic 14th day of battle.
Dronacharya arranges a combination of 3 vyuhas in order to protect Jayadratha from Arjuna. Bhima, Satyaki and Arjuna tear through the Kaurava army. At a climactic moment, with the sun nearly set and thousands of warriors still between Arjuna and Jayadratha, Krishna sends his Sudarshana Chakra in order to mask the sun and create an illusion of sunset. The Kaurava warriors rejoice over Arjuna's defeat and look forward for his imminent suicide. Jayadratha comes before Arjuna and taunts him. Krishna orders Arjuna to kill Jayadratha. With unflinching belief in his friend, Arjuna beheads Jayadratha with the Pashupatastra. The astra carries the head of Jayadratha to Vridhakshtra. When the head falls, his father gets up in shock. The head of his son falls on the ground, and Vridhakshtra's head bursts into 100 pieces. Thus, Vridhakshtra becomes the victim of his own boon granted to his son. Krishna then removes the illusion. Thus, Lord Krishna saves Arjuna and sees to it that both Jayadratha and Vridhakshtra are killed in the same stroke.
In some versions of the story, Arjuna does not use a divine weapon to send the head to Vridhakshtra. Instead, he puts on a show of archery to move the head further and further away.
When Arjuna killed Jayadratha is also a source of debate. In some versions, Krishna removes the illusion before he tells Arjuna to kill a surprised Jayadratha, not after.
After the war, Arjuna fights with the Sindhu army when it refuses to honor Yudhisthira as the Emperor of Bharatvarsha. When Dushala (his cousin) comes and begs to spare the life of her son Suratha, Arjuna complies.
Notes and references
- Mahabharata by C Rajagopalachari. 2008 (52nd) Edition by Bhavan's Book University. ISBN 81-7276-368-9
The reference from the:
- Mahabharata book is prefixed by ''Mahabharata''