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Nihilus
Nihilus was a Sith Lord almost 4,000 years before Darth Sidious wiped out most of the Jedi. While he was living, Nihilus was winner of Biggest Asshole In The Galaxy award every year.

Nihilus was involved in the Mandalorian Wars, and survived the Battle Of Malachor V. It was there that a Mass Shadow Generator basically made, you guessed it, a mass shadow. This shadow was not like regular shadows though in that it destroyed almost everything is came in contact with. Having lived through that though, Nihilus now had a hunger for Force energy. It may have been a tape worm, we'll never know.

In time he met Darth Traya, and then they met Darth Sion and made a power trio, ahem, a Sith Triumvirate. They were tuff!

Darth Nihilus took on Visas Marr as his apprentice on Katarr, who ultimately assisted in defeating him.

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