Shikhandi
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Shikhandi (Sanskrit: शिखण्डी, Śikhaṇḍī, lit. lock on the crown of the head) was born as a daughter named Shikhandini to Drupada, the Panchala king, and later became Shikhandin after obtaining manhood from a Yaksha named Sthuna. In his past life, Shikhandi was Amba, one of the three Kashi princesses, who wanted to kill Bhishma in her next life. Shikhandi causes the fall of Bhishma on the 10th day of Mahabharata war, as Bhishma had an oath not to fight a woman or the one who had been a woman. Shikhandi was the elder brother of Dhrishtadyumna and Draupadi. Kshatradeva was Shikandi's son.
Past life
Shikhandi was Amba in his previous birth. Amba was the eldest daughter of the King of Kashi. Along with her sisters Ambika and Ambalika, she was taken from their Swayamvara by force by Bhishma, as punishment to the Kingdom of Kashi for not inviting Hastinapur nobility to the event. After defeating several kings, including Salwa, the King of Saubha, Bhishma absconded with the princesses and presented them for marriage to Vichitravirya, the crown prince of Hastinapur.
Vichitravirya married only two sisters, because Amba told Bhishma that she had fallen in love with Salwa, and was not ready to marry anyone else. Hearing this from her, Bhishma sent Amba with grandeur to Saubha. But Salwa rejected her as well, in shame of losing the combat against Bhishma. Amba then returned to Bhishma and demanded that he marry her according to Kshatriya dharma, but Bhishma declined due to his vow of celibacy. Enraged at her humiliation, she tried to persuade other kings to wage a war with Bhishma and compel him to wed her. None agreed for they were afraid of incurring the wrath of the great warrior. Amba got Parashurama, Bhishma's guru, to champion her cause. However, not even Parashurama could defeat Bhishma.
Amba then resorted to penance and obtained a boon to cause Bhishma's death. Eventually, her prayers were answered. But, being a woman with no military training, she asked Shiva how she would accomplish her task, and he responded that her future incarnation would be the one to actually bring about Bhishma's demise. Eager to bring this about, Amba entered fire and was reborn as Shikhandini, the daughter of King Drupada.
Gender
Shikhandi was born female who later became a male. When Shikhandini changes his sex, he becomes Shikhandi. Drupada desires an heir and prays to Shiva who given him a boon of a daughter who will later become a son. Drupada raised his daughter as a son and had Shikhandini married to a princess of Dasharna. She complained to her father, Hiranyavarma, that her husband was a woman. When the king sent people to check this fact, Shikhandini panicked and escaped into a forest, where she met a Yaksha named Sthuna who exchanged his sex with her. The Yaksha king Kubera sees the Yaksha as a girl and curses him that he will remain in the form till Shikhandi dies, keeping the sex-swap in place.
Role in the war
In the battle of Kurukshetra, Bhishma recognised him as Amba reborn, and not wanting to fight a "woman" (or an actual woman, depending on the version), avoided battling Shikhandi. On the tenth day, Shikhandi rides in Arjuna's chariot, and together, they face Bhishma, forcing him to lower his weapons. Knowing that this would happen, Arjuna stood behind Shikhandi and attacked Bhishma with a devastating volley of arrows. Thus, Shikhandi was instrumental in Bhishma's death.
Shikhandi was killed by Ashwathama on the night of the 18th day of battle, killed dazed and confused, Shikhandi is killed in a sword fight with Ashwatthama when Ashwatthama, Kripa, and Kritavarma attacked the Pandava camp on the night of the final day of battle.
12th day of war
The youthful Vikarna of great wisdom resisted Shikhandin, the youthful son of Yajnasena, as the latter advanced in that battle. Yajnasena's son then covered the former with showers of arrows. The mighty son Vikarna, baffling those arrowy showers, looked resplendent on the field of battle.