Principal W. Seymour Skinner. Depending on who you ask, the man is a either a champ or a chump. That being said, most of Springfield would probably say chump. It's actually hard to say who would use the word champ. Regardless of how little respect you have for the man, it's hard to deny that he hasn't pulled some genius moves on occasion.
Unfortunately for him, his moments of brilliance are far exceeded in number by his moments of sheer idiocy. But you have to give him credit for always being entertaining.
Genius: Getting Rid Of Evita (Lisa)
First and foremost, it's important to note that the producers of The Simpsons have never heard of any musical based on the life of Eva Perón. They were very clear on that at the end of the episode. In "The President Wore Pearls," Lisa successfully ran for student body president.
Skinner and the faculty tried to manipulate her but she resisted them. Skinner got rid of her by transferring her to a nearby school for the Academically Gifted and Troublesome. The only flaw in his plan was that Homer was/is super lazy and refused to drive her every morning. So, back to Springfield Elementary.
Not Genius: Steamed Hams And The Northern Lights
In "22 Short Stories About Springfield," a series of shorts depict what life is like all over the city, mostly away from the Simpsons. Principal Skinner was having Superintendent Chalmers over for supper. Skinner being Skinner, he burned the meal and had to sneak out to get hamburgers from Krusty Burger.
He then had to embark on an insane web of lies to cover this up, including trying to convince Chalmers that the burgers were called steamed hams and the raging fire that was slowly engulfing his house were the Northern Lights. The worst part was Chalmers seemed to be buying it.
Genius: Fake Comptroller
When Lisa cheated on a test, she accidentally ended up bumping the school's grade point average up to the state's minimum requirement. This was a huge win for Skinner as they finally qualified for a basic assistance grant. Unfortunately, Lisa couldn't live with the lie and wanted to come clean.
Skinner orchestrated a sham ceremony with Otto impersonating State Comptroller Atkins, giving her the opportunity to be honest while the school still got to accept the cheque. It's also important to note that this episode featured Pinchy, Homer's beloved and delicious pet lobster.
Not Genius: Screwing Up With Krabappel
The most significant relationship of Skinner's life was with Edna Krabappel. She almost made him act like a fully grown adult man with any kind of backbone. Naturally, he was almost at the finish line when he completely screwed it up.
Edna had agreed to marry him but also knew of his doubts about her and their relationship. She ended up walking away from him and eventually marrying Ned Flanders. Skinner never really recovered from losing her, though he still would have had to deal with it as Edna later ed away.
Genius: Tricking Bart
The relationship between Bart and Skinner is fairly one-sided, with Bart normally getting the better of his principal. But every once in a while Skinner actually manages to get one over on Bart. This happened in an episode that was an homage to The Departed. Skinner needed eyes and ears inside of Bart's organization so he found an orphan he could place in the school that Bart would end up trusting. Skinner used his mole to get intelligence on Bart's operations and also managed to sew mistrust amongst his crew.
NOT GENIUS: Billy And The Cloneasaurus
After a school visit from Santa's Little Helper went awry, Chalmers fired Skinner. But Skinner put the time to good use by working on his novel, "Billy and the Clonesaurus." It's a completely original story that sounds nothing like Jurassic Park.
Well, except that it is exactly like Jurassic Park, a blockbuster novel and movie that Skinner had somehow never heard of. Luckily for him, Apu was on hand to spend a solid ten to 15 minutes berating him about his ever so slight oversight.
Genius: Saved Himself From A Pile Of Newspapers
Bart had a rough day at school and accidentally found himself in the Legitimate Businessman's Social Club. Once there, he was face to face with Fat Tony and company.
Bart became their bartender and associate. But after finding out that Skinner was making Bart's life difficult, Fat Tony vowed to do something about it. People thought Skinner was murdered on Bart's order but it turned out he was in his garage, trapped under a huge pile of newspapers. Not shockingly, the Springfield Police couldn't find him but Skinner was able to free himself by constructing a rocket out of garbage.
NOT GENIUS: Dating Patty
This is just not a good idea at all. Skinner isn't great with women but there had to be a better choice than Patty Bouvier. Keep in mind that her middle name is Maleficent for a reason. She's not a particularly pleasant person who is perpetually on a mission to destroy Homer with the help of her twin sister Selma.
It wouldn't have worked out anyway as Patty eventually came out of the closet. But maybe if she had dated Skinner longer, it would have helped her get to that realization sooner.
Genius: Becoming Seymour Skinner
In the second episode of season nine of The Simpsons, it was revealed that the man Springfield knew as Seymour Skinner was actually Armin Tamzarian. They found out when the real Seymour Skinner was finally freed from the Chinese sweatshop he ended up in after his time in a POW camp. Armin and Seymour were in the same unit in Vietnam.
When Seymour went MIA, Armin delivered the news to his mother and fell into his life. This move gave Armin some sort of future, which there wasn't much chance of in his former life.
Not Genius: Becoming Seymour Skinner
The problem with becoming Skinner meant that Armin took on everything in his life, including his mother. Agnes Skinner is a horrifying human being on every possible level. She does love her son in her own overbearing way. But who knows what Armin's life would have actually been like if he had just stayed as himself? It's hard to say since Springfield is such an all-consuming place. Armin might have been a rough guy before the war but his time in Vietnam changed him. Plus, he's stuck with Agnes, who will inevitably outlive him.