Playing With / Ambiguously Evil

Basic Trope: A seemingly evil character turns out to be hard to clearly categorize anywhere on the good-evil continuum.
  • Straight: Antonio works knowingly with the Big Bad, for purposes that probably are not what he says they are and puts effort into inconveniencing the heroes. Even so, the main villain is in for it if erring to do certain kinds of things (or demand Antonio to do so) - something made clear implicitly or explicitly. Antonio actually avoids directly harming the heroes if it seems to serve his (unknown) objectives in the slightest. He avoids crossing certain lines and claims it's for pragmatic reasons, but there seems to something else to the story.
  • Exaggerated: Antonio fights alongside bad guys without looking the slightest bit bothered about this. He constantly sabotages the heroes' efforts, covertly manipulates, arranges and influences situations to his advantage and leads people on wild goose chases while he seems not only to be wise to mind games played by villains, but also to possess a lot of information he's withholding until he sees it necessary to reveal a small something to someone. However, he also goes to extra lengths to refrain from doing anything too extreme, provocative or vile. In a few instances he even ends up helping a hero avert a danger or doing them a favor and matter-of-factly stating afterwards that it happened to serve his own objectives. He seems to be willingly forthright about many things to some characters, telling about possible dangers facing them from different directions and likely consequences should they choose certain courses of action while warning them there are things they are better off not knowing. Many of his actions turn out to be smoke and mirrors to fool heroes, villains and/or whoever he happens to meet. Some of his cryptic statements ends up being of help to some characters.
  • Downplayed: Antonio seems shady. Though he's relatively overt about warning the main characters not to proceed on their way, there is a lot he is plain secretive about - while pulling attention to this and claiming everyone and everything else is something else than it seems. He actually tries giving the main characters something useful like money to get them to leave while relating reasons why it's better for them to leave, telling stories about horrible things happening(it's unclear how much is real and how much is made-up or distorted). At the same time he stirs up suspicions for them in locals, persuading them to create a subtly uninviting athmosphere to make sure the main characters do end up leaving.
  • Justified:
    • Winning the trust of the villains is the quickest and the most effective way for Antonio to advance his own goals.
    • Antonio is a Wild Card Magnificent Bastard playing all sides against each other.
    • The setting thrives on Grey and Gray Morality, and Antonio is milking the trope for all it's worth.
  • Inverted: Antonio is an Anti-Hero note 
  • Subverted: Antonio commits something so vile as to shake off ambiguity like sending thugs to beat someone up because of getting too near to the truth.
  • Double Subverted: Though Antonio claims to be behind it, this actually turns out to be false and someone else did it instead. Why Antonio says he had any hand in it, even indirectly, is a question indeed.
    • It starts to be very dubious throughout the story whether Antonio actually has had any hand, even indirectly, in committing the kinds of deeds he says he has.
  • Parodied: The organisers of the annual VillainCon have lengthy debates each year over to whether or not Antonio should be invited.
  • Zig Zagged: Antonio constantly changes sides.
  • Averted:
    • Antonio can be doubtlessly seen as evil.
    • Alternatively, Antonio is clearly good.
  • Enforced: "Grey and Gray Morality is all the rage these days, we should get rid of some of Antonio's more heinous acts, so he can remain ambiguous."
  • Lampshaded: "You know guys, for a villain, he doesn't seem all that bad."
  • Invoked: "As long as I don't do anything truly evil, I can fight for whatever side I want, and the heroes won't have an excuse to get rid of me."
  • Exploited:
    • The Hero knows that Antonio will most likely not do anything too hasty against him and his team, so he starts playing mind games on Antonio.
    • Even though Antonio's working with the Space Nazis, the heroes know that he's sufficiently uninterested in the ideology for them to just bribe him into supplying the heroes with Space Nazi secrets.
  • Defied: "If I'm a villain, then I might as well go all the way! Now, where's an orphanage that I can burn down?"
  • Discussed: "Is he really evil, or is he just messing with us?"
  • Conversed: "These, 'are they good or bad,' type of villains always wind up having the most amount of fans, I tell you."
  • Deconstructed: Antonio's refusal to commit alienates both sides. The villains can't trust that he won't sell them out, and the heroes are suspicious of his ethics. As a result, Antonio frequently finds himself fighting both sides, and is unable to accomplish any of his own goals.

Back to trying to think of an easier label than this.
http://tvtropes.org/pmwiki/pmwiki.php/PlayingWith/AmbiguouslyEvil