Alright. This could get rather long. I said a while ago on hated characters not to get me started on Gary but since we are here...
I'll be flat with you guys. I despise Gary A LOT. Perhaps more then that though I really dislike how incomplete he is as a character and yet people still flock to him and think he is such a good character. Like Hayley I cannot figure out why people love him. I respect opinions that I disagree with provided it is reinforced, with Gary... I can't find anything concrete to reinforce or any real reason to like him.
Firstly, there's a load of plotholes in the game and most of them involve Gary. I have thought about how the story could be restructed, changing Gary's character slightly. Not making him such a poor liar mostly, Jimmy wouldn't even know he's the nemesis until Jimmy was expelled and not just because Jimmy's stupid. This would make him far more meaningful as a villian (and likeable in my eyes), but have been hesitant to post this considering how many people seem to love him as is.
As Red pointed out, his character development is very weak. They establish very early on he's a sociopath, so therefore its well known he treats people like objects and are only there to be manupilated.
Yet whenever he's on screen he's an extremely poor liar who despite this still manages to decieve everybody while he's offscreen, hell its why he spends so much of the game off screen almost because it wouldn't be in his character to actually tell a good lie. "I... I mean WE are going to take over the school"... nooo you are totally not going to double cross Jimmy. Problem much?
Nobody respects him either except for Crabblesnitch and him being headboy, fair game, at least until 'I tied him up and he STILL likes me' wait what? He's a blind corrupt idiot this is well established so I'm willing to let some of this slide but how does he 'turn the school into a battleground' when Derby says after Preppies Vandalized 'I don't care about you (Jimmy) or Gary'. Johnny's only interraction with Gary is 'Shut up Gary' during Wrong Part of Town.
Earnest yes, he would fall for it, because he's also a blind idiot with no vision but Gary and the Jocks have no interraction at all. So how does this 'grand masterpiece' come together? Through the use of idiot balls (see TV tropes) of course. A very poor plot device for a manupilator and one that makes me weep everytime I play through the game. I admit, part of me wants to work on games, as a writer, designer, whatever I could do, and seeing this... yeah...
As for the Townies, I don't think Gary really had to try too hard and did he really hurt them? They did not have anything to lose. So they get a beating from Jimmy? So what? So did everybody else. They got a free pass to cause a lot of trouble, and got to beat up Bullworth kids during the riot. They came out pretty well considering they had nothing to gain otherwise.
Perhaps worst of all (and something I'd resolve with my restructure) is that Jimmy never has a real reason not to go after Gary. It's 'he's a bigger problem' Why? Or 'he'll have to wait?' Why? Then 'he's not a problem anymore?'. Jimmy carries the idiot ball throughout the entire plot in a poor attempt to make a poorly developed character look brilliant.
Now this sounds like I'm really bashing on the game, I love the characters... but the story itself felt a tad rushed, especially near the end.
I don't want to offend people but sheesh, I just can't get why Gary is thought of as brilliant when he really isn't. He's a poor liar and every single 'clever' thing he does, is done with him off screen with no real details of how his 'scheme' came together.
He becomes your best friend forever and stabs you in the back. He's the kind that would hang with you for a few years just so that when he fucks you over later, it hurts severely.
The problem is he's such a bad liar everytime we see him that nobody with real brains would fall for that act for long. Petey might be an exception because he's looking for a friend, but Gary wouldn't bother because the only thing Pete would be good for is taking the fall for something he didn't do (which might have been a nice story angle to make him more devious). However this doesn't happen...
I guess the thing now that I think about it is that maybe Gary was such a bad liar as to cue in everybody else to it except JImmy. However it comes off really poorly in my opinion.
On the other hand, I've heard some people might feel sorry for him because of his problems (and that he can't help backstabbing everybody) and feel he's doing what he's doing because he has little control and his meds make him feel awful. If this is so he could have shown minor regret or remorse, then I would understand this angle, but most of what I hear is that they think he's genius, when he's really not.
Sorry for the rant, but this is exactly why I left it. I wanted to try understand better before I ranted off. Blind fanboy/girlism, sort of bothers me. Especially when there are much better characters you could like, Derby for one, is a much better 'Magnificant Bastard' than Gary.
If anyone cares, I'll put the restructure up somewhere. Either here (since most of it is relating to make Gary as intended in the 'writers vision') or in its own topic. I do this sometimes, like place events differently as to make the story flow better if it felt a bit flat to people. On Her Majesty's Secret Service comes to mind the most here.
Conclusion: I voted he's a douche. He's not a genius. He could be misunderstood but there's not enough to back that up and to be honest he could try to make friends with people and then turn on them but considering everything, I can't see this working to any real extent. He's a poor liar, poorly developed and nothing he does throughout the entire plot is convincing enough to suggest he does anything other than rely on the power of idiot balls.