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I'm puzzled by Ashvatthaman's status as a chiranjivi. Not necessarily that he is one, but more the circumstances surrounding it. To wit, Ashvatthaman is made to wander the earth endlessly for 3000 years (and thus he is a chiranjivi) and he will bear all the diseases afflicting the world. I've heard others say that Ashvatthaman is a chiranjivi because he will take on the role of Vyasa in the next cycle of yugas, but have not been able to substantiate this claim with textual sources. To me, this all seems like an odd mixture of punishment and reward - Ashvatthaman is made immortal, and will perhaps have the honor of serving as Vyasa, yet he is clearly being punished as his perpetually diseased state demonstrates. Any insights on the why of all this?

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First let me recount the story of Ashwatthama's curse, which is told in the Sauptika Parva of the Mahabharata. After the Mahabharata war, Ashwattama, in order to avenge the death of Duryodhana at the hands of the Pandavas, and presumably also to avenge the death of his father Drona, went into to the camp of the Pandavas at night to kill them. But the Pandavas were away that night, and Ashwatthama instead killed the Upapandavas, the five sons the Pandavas had with Draupadi, thinking it was the Pandavas. When he realized that he had killed five innocent boys, he went to the Ashram (hermitage) of Vyasa to repent for his sin. Then Krishna the Pandavas found out that Ashwatthama had killed their sons, so they tracked his chariot to Vyasa's hermitage.

When he saw them, Ashwatthama feared for his life, so he launched a Brahmastra (weapon of Brahma) at them. And in response Arjuna launched a Brahmashirastra. To prevent the two extremely destructive weapons from doing any damage, the sages Narada and Vyasa came and persuaded Arjuna to withdraw his weapon. Vyasa asked Ashwatthama to do the same, but he couldn't withdraw the Brahmastra, so instead he redirected it to hit the wombs of the Pandava women. This did not serious damage, because although it killed the unborn baby Parikshit in the womb of Abhimanyu's wife Uttara, Krishna was able to bring it back to life.

In any case, for all his crimes, Krishna issued the following curse on Ashwatthama:

As regards thyself, all wise men know thee for a coward and a sinful wretch! Always engaged in sinful acts, thou art the slayer of children. For this reason, thou must have to bear the fruit of these thy sins. For 3,000 years thou shalt wander over this earth, without a companion and without being able to talk with anyone. Alone and without anybody by thy side, thou shalt wander through diverse countries, O wretch, thou shalt have no place in the midst of men. The stench of pus and blood shall emanate from thee, and inaccessible forests and dreary moors shall be thy abode! Thou shalt wander over the Earth, O thou of sinful soul, with the weight of all diseases on thee.

So Krishna's utterance was purely a curse; there wasn't any reward to go along with it.

But you are right that Ashwatthama will become the Vyasa of the next Mahayuga, as (Krishna Dwaipayana) Vyasa's father Parashara says in the Vishnu Purana:

In the next Dwápara, Drauńi (the son of Drońa) will be the Vyása, when my son, the Muni Krishńa Dwaipáyana, who is the actual Vyása, shall cease to be (in that character).

But this isn't a reward for his misdeeds. Rather, it's due to the fact that upon hearing Krishna's curse, Ashwatthama told Vyasa that he planned to be with him: "With thyself among all men, O holy one, I shall live! Let the words of this illustrious and foremost of men become true!"

So presumably it is the time that Ashwatthama will have spent with Vyasa, engaging in spiritual pursuits and atoning for his sins, that will make him deserve to succeed Vyasa.

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    Aswatthama and Arjuna, both of them launched Brahmashirastra. I would like to add some points here - both of them received the Brahmashirastra from their teacher Dronacharya. Weapons like Brahmashirastra were not given to someone easily, it must had been achieved. Arjuna achieved the excellency in archery with his hard work and thus received Brahmashirastra from Drona. Aswatthama was also an excellent warrior but he did not receive Brahmashirastra by hard work, rather Drona gave it to his son (Aswatthama) to fulfill son's demand, in affection....
    – arin1405
    Commented Oct 1, 2014 at 11:15
  • ....For Arjuna, it was hard earned and he learnt the process of launching as well as stopping the weapon. But Aswatthama was so much overwhelmed after getting this weapon that he did not pay much attention when Drona taught them the process of stopping it.
    – arin1405
    Commented Oct 1, 2014 at 11:15
  • @arin1405 Actually, the reason Arjuna could safely withdraw it and Ashwatthama could not is that Arjuna had kept a vow of brahmacharya (celibacy): "No person of uncleansed soul can bring it back after it is once let off. Only one that leads the life of a brahmacari can do it. If one who has not practised the vow of brahmacarya seeks to bring it back after having shot it, it strikes off his own head and destroys him with all his equipments. Arjuna was a brahmacari and an observer of vows." sacred-texts.com/hin/m10/m10015.htm Commented Oct 1, 2014 at 15:41
  • Yes, it can be a reason. But may be "brahmacharya" here symbolizes the hard work and concentration a student must keep when he is a brahmachari (in learning phase). Otherwise brahmacharya means leaving a life of sage without any woman. Now if we compare Arjuna's and Ashwatthama's life style, Arjuna did not follow the same while Ashwatthama remained unmarried throughout his life and did not come in contact with any woman. Hence, the brahmacharya here means the hard work, self control and concentration which is expected from a student in learning phase and Arjuna had that.
    – arin1405
    Commented Oct 1, 2014 at 15:57
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    @KeshavSrinivasan if Ashwatthama becomes the next Vyasa; would it not contradict the scriptural injunction that 'Vyasa is Vishnu incarnate'? can you please throw some light as to how this event would still uphold the authority of scriptures? Commented Apr 7, 2016 at 8:08
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In a Kannada version of Mahabaratha written by Kumara Vyasa, the author claimed that he wrote Mahabaratha by listening to Sage Aswatthama.

It was said in order to escape from the curse of Lord Krishna, Aswatthama approached his Parama Guru (guru's guru) Lord Parasurama, who was also an avatar of Lord Vishnu. Lord Parasurama felt pity at Aswatthama and agreed to help him. It was said that Aswatthama was only an instrument in Lord Shiva's plan to exterminate all the evil people from earth. Since it was Lord Shiva who entered into Aswatthama's body and exterminated Pandava forces, Aswatthama was absolved of all sins.

It was said that Pandavas met Aswathama once again 36 years later when they were travelling to the Himalayas to seek pardon from Lord Siva for their heinous crimes in war. The description says Pandavas found Aswatthama happy in the company of Lord Parasurama and Sage Durvasa in an ashram on the banks of river Ganga and Aswatthama was found free from all curses. It was believed that Lord Parasurama and Maharishi Durvasa initiated Aswatthama into Sakthi worship, which is considered to be the supreme of all modes of worship. By worshipping Adi ParaSakthi, the mother of Lord Brahma, Lord Vishnu and Lord Rudra, Aswatthama bypassed the curse of Lord Krishna.

This story is described in Kumara Vyasa Mahabharatha, which i couldn't get any English Version.

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    How does Ashwatthama know Bhagwad Gita? There were only four persons who heard it Shri Krishna Himself, Arjuna, Sanjaya, and Dhritrashtra.
    – Yogi
    Commented Sep 10, 2016 at 19:07
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    @Yogi. In one version of this story, it was Aswathama who said this. In other version, it was Lord Narayana. Anyways, Aswathama was relieved of curse by that time. Aswathama could know the Bhagavad Gita same way how Vyasa knew that. Aswathama is destined to bs next Vyasa and moreover he was relieved of curse. He could have got trikaladarshi powers.
    – The Destroyer
    Commented Sep 10, 2016 at 19:34
  • Aswathama was relieved of curse by that time. Which curse Shri Krishna's curse and what time? but I thought he would is vyasa in making and currently studying under Krishna Dwaipayana veda vyasa
    – Yogi
    Commented Sep 10, 2016 at 19:39
  • @Yogi. Curse is for 3000 years only. This Kannada Mahabharata was written recently. Even Skanda Purana says Aswathama was relieved of curse in Rameswaram by praying Ramanatha Linga. That Mahabharata version says he was relieved by praying Shakti. This could be due to Kalpa Bheda. See keshav's answer. I'm not sure how Aswathama is learning Vedas. But I think he got some powers like Vyasa (not sure just guess).
    – The Destroyer
    Commented Sep 10, 2016 at 19:50
  • Okay thanks but what is kalpa bheda? Mahabharata is not a version to ashwatthama's story. I think mahabharata is the standard text for its characters like Ashwatthama.
    – Yogi
    Commented Sep 10, 2016 at 19:55
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To realize how he got immortality, we should know about his birth.

Which god's portion was Ashwathama?

And, O king, his son the heroic Aswatthaman, of eyes like the lotus-petals, gifted with surpassing energy, and the terror of all foes, the great oppressor of all enemies, was born on earth, of the united portions of Mahadeva, Yama, Kama, and Krodha.

Yama- god of death,

Kama - god of desire

Mahadeva - one who can bestow immortality

Krodha - Anger

Ashwathama was born of the portion of Shiva.

Powers of Shiva

https://www.sacred-texts.com/hin/m10/m10017.htm

The holy one said, "Verily, Drona's son had sought the aid of that highest of all the gods, the eternal Mahadeva. It was for this that he succeeded in slaying, single-handed, so large a number of warriors. If Mahadeva be gratified, he can bestow even immortality. Girisha can give such valour as will succeed in checking Indra himself. I know Mahadeva truly, O bull of Bharata's race! I know also his various acts of old. He, O Bharata, is the beginning, the middle, and the end of all creatures. This entire universe acts and moves through his energy.

https://www.sacred-texts.com/hin/m10/m10007.htm

The time of the Panchalas ran out

Beholding him stand immovable and with uplifted hands and as an offering up to himself, the divine Mahadeva appeared in person and smilingly said, "With truth, purity, sincerity, resignation, ascetic austerities, vows, forgiveness, devotion, patience, thought, and word, I have been duly adored by Krishna of pure deeds. For this there is none dearer to me than Krishna. For honouring him and at his word I have protected the Pancalas and displayed diverse kinds of illusion. By protecting the Pancalas I have honoured him. They have, however, been afflicted by time. The period of their lives hath run out."

Ashwathama sought the aid of Mahadeva but Mahadeva enterd into his body.

Having said these words unto the high-souled Ashvatthama, the divine Mahadeva entered Ashvatthama's body after giving him an excellent and polished sword. Filled by that divine being, Drona's son blazed up with energy. In consequence of that energy derived from godhead, he became all-powerful in battle. Many invisible beings and rakshasas proceeded along his right and his left as he set out, like the lord Mahadeva himself, for entering the camp of his foes."

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