When Archimonde's invasion of Azeroth had begun and Azshara's treachery became known, Malfurion convinced Illidan to leave his queen. Illidan followed his brother. But as Cenarius and the dragons entered the battle, Malfurion came to understand that their adversaries were too powerful to fall in combat. To end the invasion, he plotted the destruction of the Well of Eternity. The idea appalled Illidan. The Well was the source of his magic — and likely of the elves' immortality — and its loss was a price far too dear for him to pay. In addition, the night elf found that he increasingly admired the powers of the Burning Legion, seeing a magical purity that underlay their chaotic behavior. Where the night elves struggled to maintain their ground, the Burning Legion's numbers did not seem to permanently diminish. The satyr Xavius seized upon his doubts, exploiting his confusion to plant seeds of distrust into Illidan's mind which made Illidan turn to seek the power the Burning Crusade were using so he could become stronger, while in his mind this was to help defeat the Burning Crusade he actually helped them by giving Sargeras the Demon Soul to make the portal stronger.
Illidan had strong feelings for Tyrande Whisperwind, a novice priestess in the Sisters of Elune. Illidan so desired to impress Tyrande that he often acted without thinking, particularly in magic; he never realized that these displays weren't quite what the priestess was looking for in a mate. But while Illidan struggled to win her heart, none of them realized that the battle was over soon after it had begun; Tyrande had chosen Malfurion almost from the beginning. Xavius knew of this and so he made Illidan's thought darker by a spell Xavius casted and soon after the thoughts of Illidan changed into thinking that if Malfurion were to die, Illidan would no longer have a rival for Tyrande's love. Finally the sight of Tyrande in the arms of his brother Malfurion shattered his final link with the defenders.
Illidan, with a new plan spurred into his mind, journeyed to Zin-Azshari. There he feigned allegiance to Azshara and Mannoroth. Illidan's plan was to obtain the Demon Soul, an artifact of great power created by Deathwing also known as Neltharion the Earth-Warder, which had the ability to close the portal which was allowing the demons to enter Kalimdor. However to put this plan in action, Illidan had to gain more power. Illidan was eventually brought before Sargeras himself, who quickly discovered the night elf's plan to obtain the Demon Soul for the Legion. Sargeras was pleased with this plan, and gave Illidan a "gift" in return for his allegiance. Illidan's eyes were gouged out, and orbs of mystic fire set in their place that allowed Illidan to see all forms of magic, and arcane tattoos covered his body. Azshara was fascinated by the "new" Illidan (who was wary of her advances), but remained cautious, sending Captain Varo'then to accompany Illidan in his search for the Demon Soul.
After the Great Sundering, Illidan scaled the peaks of Mount Hyjal, where he found a small, tranquil lake. There he poured the contents of three of the vials into the waters. The chaotic energies quickly manifested, tainting the lake and twisting it into a new Well of Eternity. Illidan's joy was short-lived however, when his brother, Malfurion, Tyrande and the rest of the kaldorei leadership discovered him - and all were horrified at what he'd done. Unable to accept that his brother had committed such treachery, Malfurion tried again to explain to Illidan the folly of his ways. The magic, he insisted, was chaotic by nature, and it could only bring about destruction so long as it existed. Illidan refused to listen, so enraptured by the magic's power that his brother seemed to him an unknowing fool. Illidan claimed that magic would be needed should the Burning Legion ever return.
The lack of remorse shook Malfurion to his core and he raged at his brother, understanding now that Illidan was lost forever to the magic's sway. He ordered him imprisoned deep below Hyjal in a jail kept far from sight and mind.
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