Interestingly, one of my better villains in an Ex-PC as well. The player is still part of the group and his character, being a Keeper of the Everflow and a Herald and Guardian of the World Tree now, may be one of the most important in the party. His first character though he designed to be a goofy and hammy villain, so making him switch sides when the player switched characters came naturally. That, and I wrote certain parts of the campaign with his character in mind. So I wanted him to stick around and stay relevant.
His name was Pheloneous (Phil-loan-ee-us). He was a pudgy Drow Star-Pact Warlock whose big schtick (besides being a flamboyant dick) was that he had been shown his fate by the star lords when he was just a child. When he was in the group there was a moment when a he outhammed a bad guy by delivering an even more cutting and over the top evil speech after the bad guy had given his own. He was fat, racist, and sniggering prick. Shortly after this session the game was put on a year long hiatus, and when it picked up the player of the character wanted to switch. So I let him. The game picked up with the party chasing a bad guy through the Underdark with the help of some Drow allies. When they returned successful from their mission to the drow city, low and behold Pheloneous shows up with an army to arrest them. The party spends some time in jail and has to plead a case of an alliance between the Drow and them to fight an Empire ruled by Tiamat. During the debate with the Matron Mothers, it is revealed that the one Matron mother who seems to be opposed to them the most, and whom Pheloneous works for, was a changling assassin working for Tiamat. When the party and the remaining Matrons storm her compound they find the real Matron and her entire family dead, slaughtered using/as part of some serious Far Realm magic, and the only living creature in the house is Pheloneous.
Pheloneous gives a brief speech about how it's impossible for mortals to tell the difference between fate and chaos, and laughs, before the Matrons blast him to bits, revealing the thing giving the speech was a gibbering mouther warped to look like Pheloneous.
After they they don't see much of him for seven levels. There was an episode when a rival rebel/terrorist group used blood magic to try and force the primal lord of the wind to cause a hurricane over a mostly innocent city, and the party received hints that Pheloneous may have been involved, now operating under the name of the Benefactor.
Come to level 11 and the party is attempting to forge an alliance with the Goliath tribes. Low and behold right when they get there they find none other than agents of the previously mentioned terrorist group, lead by a silent black robed spell caster who the others refer to as the Benefactor, also seeking the alliance of the Goliaths. The party competes for the alliance, and eventually convinces the chief shaman to call upon the primal spirit whom the party had helped in a prior mission to set the story straight. Long story short, the primal lord back them up, and in the middle of the discussion, the Benefactor leaps up, kills the Shaman and his guards, and then is blasted to bits by the primal spirit. Then the party returns to the village to find it being attacked by agents of Tiamat there, looking for them based on an anonymous tip. The party manages to save the day and earn the alliance of the Goliaths and the more or less permanent friendship of the Primal Spirit.
After that there is another 7 level gap of no contact. Along the way the party learns from an allied faction that supposedly they caught the Benefactor and killed him while he was doing... something to an aquafer... three months before the party saw him killed by the primal spirit. Then, shortly thereafter, a plague of Far Realm origin begins sweeping the continent. The party puts two and two together.
Eventually another NPC gives the party location of the terrorist organization. When they go to the city that they've conquered they find it burnt down and filled with dead, both from combat and the plague. After an unpleasant meeting with a family member, the party finally gets to confront the head of the terrorist group whose been a thorn in their side for so long, the Turathi Highborn... and find him to be a hollow insane wreck dying of the plague he helped unleash and surrounded by the plague wracked corpses of his own followers, convinced he's ready to defeat Tiamat all on his own. The party, for how much they hated the blood-thirsty arrogant prick, feels nothing but pity for him. Unfortunately they don't have much time to do so since his only decent follower kills him, causing his nifty cloak to reveal its infact an ancient plague spewing Far Realm horror as it comes to life and tries to kill the party. Fun Fact: It used the Highborn's still conscious body as a literal meat-shield to absorb damage. As in stabbing, blast, and radiant damage. While he was helplessly under its control and still alive and feeling every second of it.
Well, after they defeat the Far Realm horror it collapses and attempts to escape in the chaos. They chase it down only to have it be stopped, grabbed, and swallowed whole by a very familliar figure. Granted, his body is completely different, but no one in the party could forget his smile.
Pheloneous combines with the cloak/mimic/plague thing and then greets the party, commenting that they haven't seen one another since they watched him tossed off a mountain by an angry wind spirit. When the party is less than receptive he makes note that, thinking on it, he's an absolutely terrible villain. Every action he committed has seemed to end in their favor. His attempt to sabotage their relationship with the Drow by coaxing Tiamat to interfere only made it stronger. Same with his pig headed idea of willing walking up to a primal spirit he had helped magically brainwash and murdering the shaman, on top of once again calling in Tiamat's inept forces to prove the party's point that an alliance was needed. Truly an awful villain.
He then also comments that it was odd for him to pick the name Benefactor since his actions did not benefit anyone who he was supposedly helping. Truly strange... if one assumes he was helping the Highborn.
Pheloneous then reveals that in fact his actions were designed specifically to help the party and the party alone. He has done his best to insure they had the strongest allies they could, interfering in just the right ways so that they always came out on top. Hell, he even made sure that the Highborn wasn't an issue anymore. What of the plague he unleashed though? How is that helping anyone? Pheloneous revealed, calmly, quietly, and politely that the plague, which had killed hundreds of thousands at this point, was his masterstroke. When it started, Tiamat quickly developed a cure. She then deliberately sent it to the party, in hopes of using the fact that they were not getting sick to frame them for the plague. The party turned around and began secretly spreading this information to the populace. The plague and the political shadow war around it quickly radicalized and polarized the populace... which was Pheloneous's plan all along. The plague divided the nation between Tiamat and the Party, ensuring that no one couldn't help but pick a side. In short, the plague was his greatest gift of all to the party: it was the elimination of moral ambiguity from the war. No ifs. No maybes. No just following orders. Everyone playing a part knew what they were getting into and chose to do so willingly. The party could carry out the coming war with Tiamat without fear of harming innocents, because no one was innocent anymore.
Pheloneous then revealed that it is both in his and his masters' intrest that the party succeed, and that in fact everything he had been doing for the last 50 years of his life had been towards that end. For him, Fate is set in stone and its only his place to carry out his nature, which is to serve the Lords of Infinity (the creatures who rule the Far Realm). Much as the party can't help but carry out theirs. Ultimately everything is moving towards the inevitable mechanistic end of the universe, when the Lords of Infinity invade and kill and consume Pelor, and thus time itself, as it has been since the dawn of time. He and the party are but cogs moving towards that end. He then begins dropping hints that he is directly (or indirectly in his own mind), responsible for several of the more
ed up and character defining aspects of the PCs' backstory, ensuring they would be who and where they are now, so that they can play their part in the story of Fate. He says flat out that in a way he is more responsible for their creation than their fathers were. Granted, some of the things he said were vague, and he could very well be lying and insane... but he could just as likely be telling the truth.
After that he just kind of... walks away. He makes it clear his goal is not to kill them, and implies that if they tried the reverse it wouldn't work. Not now anyway. So the party lets him go. Since then, as things continue to degenerate, the party has been growing paranoid about what may or may not be Pheloneous's work in it all, knowing that some day their going to have to face him and most likely his dread masters.
Time will tell though. Time will tell.
