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I feel that some entries are confusing this with Beware the Nice Ones. This should be reserved for characters who are legitimately good, but are much more sly and clever than their peers would expect.
For Star Wars, I think we should add Luke Skywalker. He is a genuinely good person who is frequently underestimated because of it:
Vader and the Emperor expected Luke to either turn to the Dark Side or die but instead Luke took a third option and redeemed Vader, something that even Obi-Wan thought was impossible.
Prince Xizor and Jabba the Hutt both thought they could kill Skywalker and paid for it with their lives. Ditto for Orman Tagge, Kharys, Cronal, and pretty much everyone else who has ever tried to kill him.
Mara Jade thought that Jabba could handle Skywalker and only realized she was wrong when it was too late to do anything.
Thrawn seriously expected the Noghri to capture Luke Skywalker.
What happened to the image? There was one from Order of the Stick in here
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