Night Below: An Underdark Campaign is a classic AD&D adventure that I purchased when it came out in the 1990s but which I never got to run all the way through until the 2010s. Beginning with D&D 3rd edition and eventually converting to Pathfinder, my final version of the campaign saw some changes, including revising the Rockseer elves and adding a secret villain behind the aboleth conspiracy: the Red Mage.

Well, that was certainly unexpected.

Last fall, my players greased up a rowboat and sent it hurtling down a waterslide of doom. They wound up in an entirely different world that used a version of the classic AD&D module Dungeonland, tweaked to fit with Pathfinder 2nd edition. And, well…they found a way out of Dungeonland. And now they have a bigger boat.

Over the course of several years, I ran Night Below: An Underdark Campaign in a multi-year game that spanned the gap between Dungeons & Dragons 3rd edition and Pathfinder 1st edition. As we entered the endgame, the PCs learned that a group of aboleths had been kidnapping spellcasters in a bid to power a mighty structure that will extend their natural psychic domination abilities across the globe, effectively taking over the world.

Recurring villains are one of those storytelling elements that just seems next to impossible to translate into a role-playing game. A villain needs to make the players want to hate him, but he also needs to survive contact with the group. It’s easy to do one, but not both; if the players really hate a villain, they’ll often go all out to defeat him, plot be damned. There are only a handful of ways to keep a villain in live in that case: keep him behind a glass wall, illusory projection, or similar device to bestow plot armor, make him powerful enough to take the whole group on and win (in which case you run the risk of the players not knowing when to retreat), or use cheap GM fiat tricks to guarantee his survival…in which case you’re taking the “game” out of “role-playing game.”

I’ve been on both sides of the table on the matter. As a GM, I’ve watched guys I expected to be major villains gunned down, stabbed, or tossed out of windows. As a player, I’ve gone on murderous rampages to take down bad guys, sometimes sacrificing my own characters and sometimes ignoring the positive aspects of a villain’s personality because of my seething hatred of them. (In particular, my friend Nick once ran a game with a very good samurai villain who was not actually a bad guy but rather honor-bound into serving the big villain. He eventually tried joining the group, but I was so sick of getting my ass kicked by him at that point that I was quite hostile in the role-playing interaction, much to the detriment of the game.)

I’ve played RPGs for about twenty years, but I’ve only had a handful of really good villains. One of them is a decade old now and still going strong, much to my delight and the anguish of the players. Hailing from various Dungeons & Dragons and Pathfinder games, his name is Derrezen, but he is best known in my games as the Red Mage. This is a look at how he got introduced, what worked for him and what didn’t on his rise to villainy, and why he became a character my players loved to hate.