The relationships of Sheev Palpatine.
- Main article: Darth Vader
Formerly Anakin Skywalker who turned to the Dark Side by the Emperor. He owned Darth Vader like a slave, but together the two were the most feared beings in the galaxy. For many years before his fall to the dark side, Anakin had considered Palpatine to be a good friend and even another mentor, not realizing Palpatine was swaying him to his side, turning him against his fellow Jedi. Palpatine preyed on Anakin's doubts, fears, his ego, and his desperation to save his wife, hinting of a secret to save others from death. When Anakin finally fell and swore himself to the Sith, he realized he'd been tricked but could never go back to the Jedi.
Palpatine never really considered Vader his apprentice but merely his pawn and enforcer, and a broken one after Vader's injuries. Both Sith Lords hated each other but we're forced to tolerate the other to secure their grip on the Galaxy with the Empire as their tool.
- Main article: Maul
Palpatine aka Darth Sidious kidnapped Maul from his mother when he was young to raise and train him to be his apprentice. Maul trained hard under Sidious, whom Maul gained some sense of attachment to and thus devoted himself to serving his master's will. When Maul was seemingly killed by Obi-Wan Kenobi, Sidious felt no real loss and simply replaced Maul with a new apprentice.
Over ten years later, they met again, Maul pretending to wish to serve Sidious again but the Sith Lord saw through Maul and duelled him and his brother, the latter of whom he killed while taking Maul to use as he saw fit. He used Maul as bait to lure out his mother and kill her, and when Maul escaped Sidious no longer considered him a real threat.
Maul's hatred and bitterness against Sidious (and the Sith as a whole) spurred him to find ancient Sith artifacts to use to exact his revenge.
- Main article: Yoda
As the Grand Master of the Jedi Order, Yoda was the very embodiment of the organization that Palpatine most despised and that posed the greatest threat to his rule over the galaxy. For many years, Palpatine concealed this disdain, acting as though the Jedi Master were a trusted friend. After the rise of the Galactic Empire Palpatine's true nature was revealed, and Yoda engaged him in a duel in hopes of toppling the Empire before more evil could be done. Yoda's attempt failed but he managed to escape; perhaps fearing his continued existence, Palpatine was eager to capture Ahsoka Tano in the hopes that she could lead him to any surviving Jedi of which she was aware.