if you're interested i have 3 (!!) such stories to tell. all in the same campaign. i have just returned to DMing after a long time, and have decided to start at 3.5. playing in Eberron the villainous group was supposed to be themed upon The Dark Six. the party started at 2nd level.

at their first adventure the party met The Fury- a shifter were lion babrbarian of high level. it was together with part of it's tribe, and the party had some city guards. the party was supposed to be awed, to fear it, and focus on secondary targets.

i forgot i was dealing with players.

they focused on the Fury, who i played badly- focusing on trying to find and stop a merchant with a secret. they whittled down it's impressive hitpoints slowly, until suddenly the half giant psiwar rolled a triple crit, taking her to below 10! death touch by the necromancer, and she couldn't even be revived.

she was supposed to be a recurring villain, and had some rolesin the campaign. oh well, time to readjust...

on their second adventure they met at the end some homebrewed creation of mine- The Devourer: a sort of a barghest only made out of an elf and panther instead of a goblin and wolf, with some druidic powers. now this will put the fear into them!

it was the most depressing defeat i've seen, they butchered it, haunted it, mutilated it slowly. obviously, i had a lot to learn of villain design

so for the 3rd adventure i turned to the forums to help in designing the Keeper: a cleric of The Keeper (obviously) turned bone knight. the party were a about 6th level meeting him. at first encounter they ran. the second encounter i hoped they would run as well, and focus on secondary targets.

i don't always learn from past mistakes. they decided to duke it out.

now this turnedo ut to be one bloody amazing epic battle, going back and forth, using every possible resource, tactic, and at the end endangering their entire mission on the chance to take this guy down.

and just as before, the half giant rolled a triple crit, taking my second in command BBEG out of the game.

oh well, time to readjust, but it was as hell worth it! one of the best moments in the campaign!

the other villains were (mostly) much better!

TL;DR- i lost 3 major villains on my campaign prematurely. i learned from that and it gave me a great opprtunity to challenge myself and improve the campaign. and it sure did!