Nobody wants to be expelled from school. It's bad for your future, rather humiliating, and your parents definitely won't be happy. For many students, nothing seems worse than doing something so bad they get kicked out of their school permanently.
Then there's this student: Expulsion isn't as big a threat to them because it's already happened to them, often multiple times, for multiple reasons. If they're trying to avoid it, it's because it's such a common occurrence for them and they'd prefer to stay in school for once, rather than because they truly care about their classes. However, often times this is used to characterize the stereotypical "bad" boy or gal, who believes that School Is for Losers and wants to rebel just for the sake of rebellion, or just doesn't care about school. Occasionally the student is, instead, a Cloud Cuckoolander or just a bad luck magnet, whose oddities have created enough trouble to get them sent from school to school. Other times, they're acting out due to a difficult life, and this is the result. Whoever this character is, they are given this trait to mark them as someone who is a very poor, very trouble-making, student, even if they have good intentions.
Sometimes a point is made about this character being such a bad student, other times it's referenced as backstory. What matters is that the character is at least mentioned as having been kicked out of several schools, and is used to emphasize their struggles with school, a particularly rebellious attitude, or both. In downplayed examples, the student may only be kicked from one school, but still has a struggling behavioral record and the expulsion history behind them.
Compare/Contrast with Tragic Dropout. Might be a reason for a character becoming a New Transfer Student or the school's Token Rich Student, and may result in the character going to a Dustbin School or Military School.
- She-Hulk's former Kid Sidekick Southpaw had been expelled from several schools before being sent to live with her grandfather, who also happened to be Jennifer Walters' boss. He palms her off on She-Hulk, ostensibly so that she'll learn what it's like having to deal with someone with superpowers and poor impulse control.
- In Robin Tim's Brentwood classmate Buzz Cohen is only at the boarding school because he was expelled from all the other schools in the area due to his quickly changing moods and tendency to swing unexpectedly into violence.
- Spider-Man: Used to Hand Wave Harry Osborne attending the same public school as Peter despite coming from an incredibly wealthy family. It's said that he was kicked out of every private school his father had him sent to.
- Batman Begins: Bruce Wayne returns from Princeton to attend the parole hearing for Joe Chill, the man who killed his parents in a botched mugging. Alfred asks Bruce how long he'll be staying, and Bruce says he's not going back because he's been kicked out. The visual dictionary remarks on this exchange that Bruce has spent the past several years being kicked out of every university in the Ivy League. This is probably meant to establish the adult Bruce as a directionless layabout due to not properly coming to terms with his parents' murder.
- Small Soldiers: Played With, as Christy believes that Alan moved to town because he was kicked out of ten different schools, whereas Alan insists that it was only twice.
- In Toy Soldiers, half the students in the prep school have been expelled from other schools. Their history of disobedience comes in handy when terrorists take over the school.
- In the Dinotopia miniseries, David tries to explain his brother Karl disobeying a curfew to Matriarch Rosemary this way.
David: Karl has a little problem with authority. He's been kicked out of eleven schools.
- Hidden Talents: Edgeview Alternative is the Dustbin School for students (and teachers) that no other school will take. The protagonist Martin is transferred there at the beginning of the book after one too many verbal altercations with teachers, but comes to bond with other students who got booted out of the conventional school system due to their unrealized Psychic Powers.
- In Night World, Thea and her cousin Blaise have been expelled from at least five schools since they were sophomores (Thea can't even remember if it was actually six). The reason is Blaise getting them into trouble with her many boyfriends, whom she puts under love spells and manipulates into doing crazy things for 'fun'. Thea doesn't go into depth about these incidents, save for mentioning that at their last school Blaise's boyfriend burnt down the gym for her.
- Percy Jackson and the Olympians: Ever since he was a child, Percy was a Weirdness Magnet with an unlucky streak. Through no fault of his own, he wound up getting into so much trouble he'd been kicked out of at least six different schools in as many years. During the series, he'd been expelled from at least one other school for similar reasons.
- In The Twinkie Squad by Gordon Korman, Douglas Fairchild (son of a US Ambassador and the only average person in a family of exceptional people) deals with his insecurities by acting bizarre so he doesn't have to be compared with his more successful siblings. He's tossed out of every private school in Washington, D.C. until the public school system is the only option left.
- In the P. G. Wodehouse school story A Prefect's Uncle, Farnie has been expelled from most of the schools he attended previously, including Harrow and Wellington. He quickly proves to be a cause of trouble at Beckford, too.
- Flat Escardos got dropped like a hot potato by every single teacher in the Clock Tower except Lord El-Melloi II, who normally only gets the absolute best and brightest students. Flat is actually a very powerful mage; it's just that his grasp on magical theory and reality in general is so shaky everyone around him can sense there's something off about him, and his Cloud Cuckoolander tendencies don't help. At all.
- Tilly from Harmony (2016) is kicked out of a standard classroom, then an autism classroom, then a private special ed school, and even manages to fail at homeschooling. Her family moves to Camp Harmony partly because they can't find any better options.
- Max from Saving Max has cut a swath through Manhattan's schools. Even the special schools have kicked him out.
- House of Anubis:
- It's not made into a big deal, but Class Clown Alfie's reason for not staying at the sit-in protest with Patricia, Fabian, and Nina is that Victor had threatened them all with expulsion, and, in his own words, "My Parental Units would freak if I got kicked out of yet another school." Though he's known for joking, with the characterization of his parents as strict and displeased with him, it's likely he really has been expelled from other schools due to his immature nature.
- Season two's new student Eddie is a bad boy from America who got sent to the British boarding school because he'd been expelled from every other school he'd gone to in the States. At first, he's completely willing to get himself kicked out of his new school, too, so much so that when he actually does get expelled by Mr. Sweet, he's less upset about the punishment and more upset that Mr. Sweet had also expelled Class Representative Mara. It's heavily implied his trouble with educational authority is because Mr. Sweet is his father, and had become a Disappeared Dad when Eddie was just a kid.
- The Outer Limits (1995): In "Straight and Narrow", Rusty Dobson was expelled from several schools before his mother Marianne sent him to Milgram Academy.
- The Suite Life of Zack and Cody: London Tipton, being the daughter of an extremely wealthy hotel owner, has attended many different private schools over the course of her life (and has also been Held Back in School a few times). However, by the time Zack and Cody started high school, London's been kicked out of so many private schools that Mr. Tipton is forced to enroll her in a public high school (the same one that the twins are going to). This carried onto the next series The Suite Life on Deck, where she continued her schooling on the S.S. Tipton (the site of "Seven Seas High") with the other students and had made an attempt to escape on the first day.
- In Trust, J. Paul Getty III had been kicked out of every school in which his parents had enrolled him before moving out of his mother's house. His pent-up anger at his parents' divorce was probably a contributing factor.
- In Ugly Betty, Wilhelmina's daughter Nico has been kicked out of every prestigious private school her mother's sent her to, largely as a cry for attention. Wilhelmina eventually starts to reconcile with Nico, and sends her to the one school in Paris that hadn't heard of her yet.
- In Wicked, Fiyero has been expelled from multiple different universities for being lazy and irresponsible. During his song "Dancing Through Life", he casually says he's been kicked out of a lot of schools.
- Jimmy Hopkins, the main character of Bully, has been expelled from multiple other schools, and if he gets kicked out of Bulworth Academy he's destined for either Military School or prison.
- In Persona 5, Player Character Joker gets expelled from his high school after getting wrongly convicted of assault, and no other school would take him aside from Shujin Academy, which is a stuffy elite preparatory school, all while on probation for the assault. Multiple characters note that, if Joker gets expelled from Shujin, he's going straight to jail.
- The Order of the Stick: Tsukiko mentions once that she was "expelled from some of the best wizarding schools in the South", presumably for practicing dark magic. Or necrophilia.
- In UC, Nicodemus explains that the reason he lets himself be bullied despite being capable of defending himself is that the last N times he defended himself, he got expelled for it.
- In Spacetrawler, Nogg looks up Hwan's record and is impressed to see he's trained in every martial arts dojo in South Korea. Then Krep connects the dots for Nogg: why would anyone train at every dojo, unless they got kicked out of them all? When we meet Hwan, he really is a remarkable fighter—but he's otherwise a complete trainwreck of a person, barely holding himself together through copious drug use.
- The pilot Carmen Got Expelled! is about a teenager named Carmen who is given one more chance at finishing school after being accepted into a private academy. Carmen has to make sure she doesn't get expelled again.
- In the "Whacking Day" episode of The Simpsons, Bart is expelled from Springfield's public schools and subsequently several private schools, so Marge resorts to homeschooling him.