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The greatest pit fiend of all, the awesomely scarred, broken-winged Alastor, serves Asmodeus as executioner.

His strength is that of a storm giants, and he never speaks. It is said in the hells that if all were swept away and Asmodeus could choose but one devil as a companion, that one would be neither consort nor lieutenant, but Alastor the Grim. The story of Alastor the Grim stretches back dozens of millennia. While Asmodeus was establishing his base of power and making himself overlord of all hell, one being was constantly and loyally at his side. That was the devil that would be known as Alastor. As a lieutenant, then general in the armies of Asmodeus, Alastor rose through the ranks and proved a worthy and dependable servant to the Arch-fiend. Century upon century saw the might of Alastor grow, as he changed from form to form, but always unswervingly loyal in service to his master. For a millennia, Alastor lead the army of Nessus in the blood war, never losing a single battle or campaign. Against the incursions of the Archons, and demi-gods of the higher planes, Alastor stood his ground, gave no quarter, and slaughtered all who would defy his lord. When Bensozia was killed in Stygia, it was Alastor that was sent to oversee the removal of Levistus, administer the punishment of Asmodeus, and to ensure that Geryon became the new lord of the fifth layer. Finally, Asmodeus himself selected Alastor (then known by a different name) to be promoted to a unique form. At a private ceremony, Asmodeus spoke the words of power that would transform Alastor into a unique devil. For hours Alastor suffered as his form warped and twisted and when he finally burst forth, it seemed he had hardly changed at all, but Asmodeus could see the truth. This was no mere pit-fiend, but a unique and powerful devil hiding within its shape. Asmodeus named his new duke Alastor, and welcomed his most dependable servant into the nobility of hell. It was only a short time thereafter that Glasya brought word to her father from the court of Baalzebul. Another fallen angel names Melkor had come to see the displaced archon, attempting to broker a deal. If the Lord of Lies would commit thirteen of his most powerful fiends to Melkors service, then, Melkor would allow Baalzebuls fiends free reign to broker pacts with and harvest souls on that untapped world. Baalzebul agreed, always eager to grow his power, and plans were made. Asmodeus could not let this stand. Were Baalzebul to gain exclusive harvest rights to a new world, he could grow in power to rival the Overlord himself. As so often before, he turned to Alastor for his answer. Alastor would replace one of the pit-fiends of Baalzebul and go with Melkor to this new world. Alastor bowed in obedience and departed upon his quest. Replacing the pit-fiend was easy, with his new found strength and powers, Alastor quickly overpowered the devil and took his place. With a dozen pit fiends around him, the duke of hell marched into Baalzebuls palace and straight into the throne-room of the Lord of Lies. The great Arch-Fiend rolled his hands with anticipation, he of course intended to send many more devils into this new world to harvest its souls. But Melkor was no novice to treachery, and had already created a contingency for just such a betrayal. Melkor had worked a fabulous sorcery, where anything trying to gate from the outer-planes too middle-earth, of from middle-earth to the outer planes, would find themselves randomly tossed among the layers of the abyss. Melkor alone held the charm that would allow safe passage from his world to the outer planes. With a satisfied smirk, Melkor opened the gate and the fourteen crossed into middle-earth. While in Middle Earth, it was Alastor who orchestrated many of the early victories of Melkor, later known as Morgoth. As time progressed however, Morgoth began to suspect his allies and kept them out of his war councils and utilized them less and less. Eventually, Alastor was captured and imprisoned deep underground by the Valor and Elves who could wield magic in this world. For millennia, Alastor stalked the caverns and tunnels deep under the mountains where he was imprisoned, learning all their passageways and secrets. Still, Alastor could never break the magical seal that kept him trapped in the darkness. Then one day, dwarves who were greedily mining for mithril, broke through the seal and released Alastor. Alastor rose with great anger and drove the dwarves from their mountain home, Durins Bane they named him. It was during his imprisonment that the sorcery of Melkor had finally been undone. Alastor used his powers to open a portal to the nine hells, and transferred the fortune in treasure that he had taken from the dwarves and underground dwellers. Alastor set out to find souls, and for the next five hundred years he used Moria as a base of operations while he travelled throughout Middle Earth making pacts with men for their souls. Finally, a wizard and his party on a great quest came through the mines of Moria. Alastor could not let this intrusion stand, and confronted them. During the battle, the wizard used a powerful sorcery to slam Alastor to the stone bridge that crossed a great chasm. The bridge shattered under the force of the impact and the spell, but Alastor was able to grab onto the wizard and drag him into the void as well.