...This is why there are no ex-Assassins. Because there cannot BE an ex-Assassin...
I realize your whole post was probably tongue-in-cheek, but just in case it wasn't, this is not true, at least to an extent. Regarding prestige classes, if a character for one reason or another ceases to fulfill the prerequisites for the prestige class, he does not lose any of the benefits already gained from the prestige class but loses the ability to gain any more levels of the prestige class unless otherwise specified. I'd look up the reference but I'm lazy.
...D&D is a place where, given the right circumstances and enough time, anything can happen.
I suppose that's one point of view.
So I don't see why an assassin can't one day be good. There is nothing saying "oops because of that you're evil forever!!!" in the assassin block. Now, I understand he can not advance as an assassin anymore and that's fine, I'm doing ALL of this for the sake of story.
So the assassin has a change of heart and becomes good. Seems like you've figured it out already. You've already said you're the DM, so if it fits the story, it's okay to break the RAW.
After thinking about it, I was probably going to create a prestige class for him based off of some of the assassin's abilities while adding a Fey feel to it. Once again, the class doesn't need to be great as it's just for story.
It's been mentioned, but if you want him to become good now, how about he becomes a Slayer of Domiel? If you really want the goodness to ooze from him, make it like a paladin's conversion to blackguard. All of his assassin levels are replaced with levels of Slayer of Domiel.
Serious question time!
If he were to revert to evil, say CE CN CE as per the story above, would a group of characters, some good, allow him to travel along with them if they needed to achieve the same cause? (Artemis Entreri did so with Jarlaxle in the Sellswords books.) Also, having the evil alignment doesn't prevent you from fighting for what you believe in as far as I know, and it shouldn't affect his motivation either, just the way he goes about it.
Point I'm trying to make is, if Grendel was to travel with this party for a spell, would their be alignment problems if the party found out he was evil? Even if they needed him.
That would be up to the party now wouldn't it? Sounds like an interesting moral dilemma to let them wrestle with.
Another question: What points of the assassin class make it evil? The killing isn't, adventurers of every alignment kill. The spells? Nah, most of those are on the wizards list. Death attack is just a more refined sneak attack so unless all rogues are evil that's not it. Now the poison... If only used against true threats or in self-defense, does that make it evil?
Thanks in advance!
Something about the fact that you have to kill someone for no other reason than to join the Assassin's Guild seems to strike a chord with me.
I recently had a PC of mine become an assassin, and after having gone through the prerequisite of killing someone just to join the guild in-character, I have a lot more insight now on why becoming an assassin requires an evil alignment. My character was forced, by necessity, to do some really nasty things to get his job done. It wasn't a simple matter of "Hey, there's this guy in the other room. We want you to stick a dagger in his throat." My character had to premeditate the entire thing. He orchestrated a homicide from start to finish and had to figure out a way to do it without getting caught. Doing so meant he not only killed one NPC, but ended up killing other innocent NPCs and ruining the lives of even more innocent NPCs in the process. Originally my DM wasn't allowing evil alignments, but I talked him into this by saying my character would never betray the party and wouldn't necessarily be a villain. But after this, I actually felt a little bad about doing it, and we're talking about fictional characters! Before the whole thing I was thinking of trying to convince my DM to let me play the assassin as neutral, but the process convinced me otherwise. Let's just say it requires a certain element of vileness to become an assassin. In summation, I think it is a lot more about prerequisites than it is about class abilities.
wow, more great answers.
Ok, so i've been thinking. What alignment does this guy sound like at the end of the story? Could he be CN? Or , going way out there, could he have gone CE CN N?
Sounds solidly CN to me. He's decided to go his own way. He isn't killing solely for money anymore. He's actually discovered a certain amount of compassion, but he's still driven by revenge.
lets look at hypothetical "good" assassin and a good paladin vs. very evil orc tribe bashing on poor villagers.
The good ol' paladin leads his band of crusaders(200 of them, well trained bla-bla) to the orc encampment. about 500 males bloodlusted dumb asses there waiting.
of course




hits the fan and melee carnage breaks loose. Orcs dead, 257 orc women and children dead in crossfire and arsening and good ol' paladin returns to the villager in triumph with his 7 sergeants as only survivors(one with only one hand).
Now our "good" assassin sneaks in orc camp, poisons the chieftain, tribe goes to 1-2 month power play for the new one. few of the orc die on the competition and when the new chief is selected the assassin repeats. after 2-3 cycles the tribe breaks camp and goes to find some "friendlier" villagers.
what's more evil?
Neither. The paladin violated his code of conduct for killing innocent women and children and is probably a blackguard now.