This has bugged me ever since the latter half of the Planescape series, and especially after the events of Faction War.
How the heck did Rowen Darkwood keep a chaotic good alignment?
The guy basically tries to take over the universe and/or nearly destroys it in the process. In addition to this, a large part of his plan involves taking advantage of and brainwash a mentally unstable person (Alishon Nilesia) who he then sells into slavery. This is just the end game of a longer scheme and a lot of other acts.
And all this time, he remains chaotic good?
Okay, so Rowen Darkwood turns out to be the overall villain of the piece. (The "piece" here being the Planescape background/story.) That's not what I have a problem with. He turns out to be the main antagonist after seeming in the beginning to be a good guy. Still, no problem, it's a twist. I like twists, I'm a writer myself. Darkwood does a lot of morally questionable acts some of which he thinks are for the greater good, and he has a number of personal flaws. Still no problem. He's an interesting, complex, well-thought-out character.
But there is no way he is chaotic good, or even if at the start of the background he's chaotic good, there is no way he remains so. Chaotic? Sure, but good? No way.
Now, a bit of a sidenote for full disclosure. I am not an objectivist. In fact, I disagree with just about every point of objectivism. I say this because the Fated are basically a faction of Randian objectivists. Now, I have nothing against this, part of the entire background of Planescape is about conflicts between philosophies, and having objectivists out there fighting it out against the others is logical (cuz it's a philosophy).
And, even though I don't agree with objectivism, I have no problem with the objectivist faction being listed as chaotic good. There are a people who see it as such.
The problem I have with it is that Darkwood seems to be able to do ust about anythign he wants without endangering his alignment. Now, granted, he's not doing anything he shouldn't as a Taker. And, Takers don't have to be chaotic good (any alignment but lawful good) even though they are (along with the Sensates) one o the chaotic good factions. I wouldn't even have a problem with them having a Factol of another alignment (In fact, they seem like one of the factions more likely to have Factols with a wide range of alignment.)
But let's take it as a given for the sake of the argument that the Fated are (generally) a chaotic good faction. I still don't think that Darkwood (especially by the end) is in any way chaotic good. Chaotic, possibly, but I think that by the time of the events of Faction war, he should be either neutral evil (my guess), possibly chaotic evil, or even lawful evil.
From the background, we know that Darkwood was good at one time. However, I'm wondering when he would have lost his alignment, and if he was still chaotic good even when he became Factol. (Or even when he arrived in the outer planes the second time).
We know that he caused a schism in the Ring Givers and made/remade the Fated in his own beliefs. How he did so is hinted at to be either through debate with the previous factol (fine for any alignment) or through blackmail. (probably not fine for someone of good alignment, especially since the person he would have been blackmailing was chaotic good.)
Under his leadership, the Fated have a tendency to use loopholes in the law or the letter of hte law to take possession of other people's property. Let's give Rowen the benefit of the doubt here, and say that that was primarily the actions of neutral evil, lawful evil, and lawful neutral Fated, and that Darkwood was a rather hands-off Factol with such things. It certainly shows that the Fated would have little to no problem as a faction with lawful evil behavior. Fine, that's an allowed alignment for their faction.
Strangely, though, a lot of the other NPCs we know are doing this (in the Cage Guide to Sigil, Factols' Manifeseto, etc) are still listed as chaotic good. This will be important a couple of paragraphs down, so keep it in mind.
Okay, by 3/4 of the way through the background, Darkwood is involved with Alishon Nilesia, the Factol of the Mercykillers, and the two factions become allies. Okay, the personal level, I can see: Rowan is manipulative, and Alishon is nuts. But an alliance between the Fated and the Mercykillers? A chaotic good faction (supposedly) and a lawful evil one? Does this make sense, especially in Planescape where everything is about power of belief/philosphy? (remember, part of Arcadia gets sucked into Mechanus because they Harmonium violate their alignment just a bit and become too lawful neutral instead of lawful good. Does it seem in a background like that that an alliance between factions of directly opposed alignments would be stable?
So what does Darkwood do now? He tries to depose the Lady of Pain, take over Sigil (and, it's implied, by extension, the Multiverse) and almost destroys both in the process. On a personal level, he sells Alishon into slavery (!) to the Baatezu. Is this in any way a chaotic good act?! Selling someone into slavery to a lawful evil race of Fiends?! Additionally, Darkwood knows what she is in for, one of hte main parts of his backstory is that he was tortured by Fiends himself.
This has got to be an evil act. A severe requires atonement to get your alignment back type evil act. How, in any way, can it not be an evil act to convince somone you love them, and then sell them into slavery in Baator.
what I'm wondering is if it has anything to do with the philosophical beliefs of the creators of planescape. Was it Zeb Cook or another writer basically doining the Randian hero thing, with Darkwood as basically an outer plane John Galt who can do anything he wants?
This is just my current theory, and I'm curious to see what other Planescape fans think How the heck did Rowen Darkwood stay chaotic good?
Pentalarc
But to the end, he's listed as chaotic good.
This ruffled some feathers for me too. While I don't know the history/motivations of the various Planescape writers; I had always assumed that, Darkwood fell into the category of characters that were designed for one purpose but then re-written as the needs of the campaign grew (e.g. Rary "the Traitor" in the Greyhawk campaign) rather than a statement on Objectivism.
Admittedly, I suspect that it was a case of sloppy editting by not updating Darkwood's alignment when his role in the cosmic drama expanded and I think a shift in alignment was definitely implied (even in early Planescape, he seemed more Neutral to me than CG). But not having worked with the actual authors, I can't definitely say what they intended
Earlier I had brought up some of my confusion regarding Darkwood's timeline and his alignment where I brought up the following idea
/forum/timeline-factol-darkwood
"I also realized that Darkwood illustrates the Unity of Rings and the Rule of Threes with regards to his alignment.
He supposedly started off as "good" (although, I don't recall him ever REALLY acting that way), his behavior when initiating the Faction War is neutral (at best); and then when he gets thrown back into the distant past and becomes the uber-powerful wizard, he seems to have taken on a more evil aura."