The story of Jayadratha
Jayadratha was able to defeat not only Bhima but also Yudhisthira, Nakula and Sahadeva, trapping Abhimanyu inside the chakravyuha and setting the stage for his heroic struggle. How was that possible?
In the Mahabharata, we hear the amazing story of Abhimanyu, the son of Arjuna and Subadra, who held his own when surrounded and simultaneously attacked by most of the senior Kaurava generals. Abimanyu was eventually defeated and killed, but only after several hours of fighting and after destroying a considerable part of the Kaurava army and killing several generals.
The reason for this sacrifice couldn't be nobler. The Kauravas attacked with a special formation called chakravyuha, where the army was organized in the form of an unstoppable chakra, that had the goal of penetrating the Pandava army and killing or capturing King Yudhisthira. Arjuna was the only one who knew how to enter and leave the formation, but on this day he was lured to a distant part of the battlefield and was not there to counteract it.
Abimanyu had heard from his father how to enter the formation, but he didn't know how to escape it. The story of how he knew such a complicated art, even though he was just 16 years old is a marvel in itself.
When Abhimanyu was still in the womb, Arjuna and Subhadrā came together one evening to have some light family talk. Gradually, the talk moved to something Arjuna had a passion for: military strategies. Arjuna started explaining the secrets of breaching the Chakravyuha, the complex formation that resembled a rotating, wheel-like labyrinth of warriors that was extremely difficult to penetrate and escape from.
Subhadrā listened attentively as Arjuna described the steps to enter the Chakravyuha, and within her womb, the unborn Abhimanyu also absorbed these teachings, learning the intricacies of breaking into the formation’s outer rings.
However, just as Arjuna was about to explain the final part, how to exit the Chakravyuha, Subhadrā fell asleep. Although Subadra came from a Ksatriya family and was not unfamiliar with military strategy, all the technical details were too much for her. Arjuna thus stopped his explanation and as a result, Abhimanyu could not learn the crucial escape strategy.
When Abimanyu explained this deficiency to his uncles, Bhima offered to cover his retreat, by following him and keeping the opening so he could exit the formation safely. After all agreed on the details, Abimanyu fought very valiantly on his chariot, breaking the formation open and attacking it from the inside. Bhima followed him accompanied by the other Pandavas (except Arjuna, who was fighting in a distant part of the battlefield). However, they were stopped in their tracks by Jayadratha, who displayed unparalleled prowess and was able to defeat not only Bhima but all the four Pandavas in their attack. As a result, the chakravyuha closed behind Abimanyu and he started his heroic struggle, which eventually led to his heroic demise.
On his purport to 1.15.16 Srila Prabhupada tells more details about the story of Jayadratha and how could he defeat the combined force of the four brothers, despite their combined efforts. In reality, Jayadratha was not a very powerful general. What to say about fighting the Pandavas, he was once beaten by Draupadi (!), falling down from his chariot when he tried to kidnap her. The story is that during the Pandava’s exile, Jayadratha passed through their dwelling in the forest and was stuck with lust when he saw Draupadi. At that moment, the Pandavas were out collecting fruits, roots, and other necessities from the forest, and Jayadratha used the opportunity to try to kidnap her. At first, Draupadi warned him of the consequences. but he insisted. When he forcefully tried to take her, she slapped him so strongly that he fell to the ground, like an uprooted tree. Eventually, Jayadratha was able to master his power overpower her, and take her in his chariot, just to be pursued and captured by the Pandavas. As you can imagine, after his heroic struggle to overcome Draupadi, Jayadratha didn't have much energy left to fight her husbands.
Apart from being publically humiliated, Draupadi beat him with her sandals which, as you can imagine, is also a great humiliation for a Ksatriya.
In this way, Jayadratha was humiliated and performed severe penances to gain a boom from Lord Shiva to defeat the Pandavas. When Lord Shiva eventually appeared to him, he told him such a boom was impossible, since the Pandavas were protected by Krsna, but conceded that one day, when both Krsna and Arjuna were not present, he would be able to briefly overpower the other four Pandavas in battle.
Just like in the case of other demons, Krsna used this blessing to engage Jayadratha in the Lila, creating the opportunity for Abimanyu to show his prowess and go back to Godhead leaving his example of courage. Of course, just like other demons, Jayadratha ended up being killed when Arjuna discovered the reason for the death of his son.
This story is explained in more detail by Srila Prabhupada on the purport:
"Jayadratha: Another son of Mahārāja Vṛddhakṣetra. He was the King of Sindhudeśa (modern Sind Pakistan). His wife’s name was Duḥśalā. He was also present in the svayaṁvara ceremony of Draupadī, and he desired very strongly to have her hand, but he failed in the competition. But since then he always sought the opportunity to get in touch with Draupadī. When he was going to marry in the Śalyadeśa, on the way to Kāmyavana he happened to see Draupadī again and was too much attracted to her. The Pāṇḍavas and Draupadī were then in exile, after losing their empire in gambling, and Jayadratha thought it wise to send news to Draupadī in an illicit manner through Koṭiśaṣya, one of his associates.
Draupadī at once refused vehemently the proposal of Jayadratha, but being so much attracted by the beauty of Draupadī, he tried again and again. Every time he was refused by Draupadī. He tried to take her away forcibly on his chariot, and at first Draupadī gave him a good dashing, and he fell like a cut-root tree. But he was not discouraged, and he was able to force Draupadī to sit on the chariot. This incident was seen by Dhaumya Muni, and he strongly protested the action of Jayadratha. He also followed the chariot, and through Dhātreyikā the matter was brought to the notice of Mahārāja Yudhiṣṭhira.
The Pāṇḍavas then attacked the soldiers of Jayadratha and killed them all, and at last Bhīma caught hold of Jayadratha and beat him very severely, almost dead. Then all but five hairs were cut off his head and he was taken to all the kings and introduced as the slave of Mahārāja Yudhiṣṭhira. He was forced to admit himself to be the slave of Mahārāja Yudhiṣṭhira before all the princely order, and in the same condition he was brought before Mahārāja Yudhiṣṭhira. Mahārāja Yudhiṣṭhira was kind enough to order him released, and when he admitted to being a tributary prince under Mahārāja Yudhiṣṭhira, Queen Draupadī also desired his release.
After this incident, he was allowed to return to his country. Being so insulted, he went to Gaṅgotri in the Himālayas and undertook a severe type of penance to please Lord Śiva. He asked his benediction to defeat all the Pāṇḍavas, at least one at a time. Then the Battle of Kurukṣetra began, and he took sides with Duryodhana. In the first day’s fight he was engaged with Mahārāja Drupada, then with Virāṭa and then with Abhimanyu. While Abhimanyu was being killed, mercilessly surrounded by seven great generals, the Pāṇḍavas came to his help, but Jayadratha, by the mercy of Lord Śiva, repulsed them with great ability.
At this, Arjuna took a vow to kill him, and on hearing this, Jayadratha wanted to leave the warfield and asked permission from the Kauravas for this cowardly action. But he was not allowed to do so. On the contrary, he was obliged to fight with Arjuna, and while the fight was going on Lord Kṛṣṇa reminded Arjuna that the benediction of Śiva upon Jayadratha was that whoever would cause his head to fall on the ground would die at once. He therefore advised Arjuna to throw the head of Jayadratha directly onto the lap of his father, who was engaged in penances at the Samanta-pañcaka pilgrimage. This was actually done by Arjuna. Jayadratha’s father was surprised to see a severed head on his lap, and he at once threw it to the ground. The father immediately died, his forehead being cracked in seven pieces."