Inadequate Inheritor

"One of the strongest natural proofs of the folly of hereditary right in kings, is, that nature disapproves it, otherwise she would not so frequently turn it into ridicule by giving mankind an ass for a lion."

- Thomas Paine, Common Sense

A successful bigwig, be it in business, politics, magic or even world conquest, is growing old, and in preparation for an eventual retirement/death looks to their children to see who among them can take up their mantle... and is faced with incompetence, disinterest, or a Corrupt Corporate Executive in the making. These are by no means an exhaustive list of possible shortcomings, indeed just about anything that can make a parent ask "Why Couldn't You Be Different?" is grounds for this trope. Special mention should go to times when the Inadequate Inheritor is not good/heroic enough, too evil, or not evil enough.

Whatever the case, the prospective retiree doesn't think they deserve their potential inheritance... at least, not as they currently are.

Cue an Impossible Task, search for a non standard heir from outside the family (who has a statistically abnormal chance to be an orphan/bastard child of the retiree), or otherwise trying to reform their potential heir or forcibly change them one way or another. Results vary: the heir may become worthy, rebel against their "benefactor" (which may be what they always wanted) or fail outright and prompt the retiree to switch to plan B, become immortal.

Expect this to be a knife through the heart of any children who just want their parent to say "I'm So Proud of You" but have been passed over. In the most extreme cases, they might get an actual knife in the heart to make way for a more suitable candidate. Especially nasty when an iron-handed Patriach crushed their spirit into Nice Guy and The Dutiful Son and now despises them for it—with bonus points if he had used the threat of Passed Over Inheritance to help crush them.

May be related The Wrongful Heir to the Throne. If the inadequate inheritor actually gets the position, through guile, lack of other candidates or sheer luck, they may either turn into a surprisingly good leader once actually in that position, or they will become a Sketchy Successor. Compare Game Between Heirs.

Anime and Manga

 * In the Yu-Gi-Oh! anime, Gozaburo Kaiba was heavily disappointed in his son Noah because he wasn't dedicated enough to be heir of his company (not to mention the fact that he was dead). So instead he adopts an orphan and gives him some Training from Hell to make him just such a ruthless manager as he himself is. Not his brightest idea, since this one is competent and evil enough, and takes over his adopted father's company quite rapidly, driving him to suicide.
 * In Umineko no Naku Koro ni, wealthy head of the Ushiromiya family Kinzo is dying. His heir, Krauss has made several bad investments and lost a lot of money. The second oldest, Eva, is intelligent and ambitious, but not very personable and is border line crazy. The third oldest, Rudolf, is just a womanizer. The youngest, Rosa has an illegitimate daughter. So what does he do to remedy the situation? Teach them to be better heirs? No.
 * In a flashback in Naruto, Hiashi states that he's disappointed with Hinata's performance and notes that the clan doesn't need a weak heir, but never goes so far as to openly disinherit her. This, however, is before Hinata Took a Level in Badass, and the two have not been seen interacting in canon since, so fan works have several interpretations over whether Hinata lost her right to inherit the clan back then, and whether she would be considered worthy to inherit the Hyuga clan when the time came.
 * A Rumiko Takahashi short story focused on a variation of this. Under insistence from her boyfriend Susumu, a woman named Nozomi pretends to be her dead best friend Noriko in order to claim an inheritance from Noriko's long dead grandmother. It helped that the last time Noriko's family saw her was with her mother when she was a little girl. Nozomi winds up receiving help from the grandmother's spirit, on the condition that the first thing she does with the money is provide a proper burial for Noriko (Nozomi was extremely offended that Susumu suggested such a ruse, but conceded because they have massive debts). Eventually, Nozomi learns that her Noriko's mother had nearly been disowned by the family for eloping with a man, and only came back once when Noriko was a child to meet grandmother. It's implied that the grandmother didn't like the family any more than Noriko's mother did, as she made it clear that no one other than Noriko could touch the property registry. It's also implied that the family might have killed the grandmother themselves.

Comic Books

 * Golgoth, a villain who took over the world in Empire, has been grooming his daughter who is an innocent princess lookalike, to take over after him. He discovers she actually killed his wife because she was holding him back and did several other very, very bad things. Following his example.
 * In The DCU, Darkseid is known to take a dim view of any of his lieutenants actually being able to control his empire after he dies... especially his son Kalibak.
 * Of course, when he so much as disappears for a few days they immediately descend into declaring open war on each other, so it's probably a justified view.
 * Subverted in Watchmen with Ozymandias/Adrian Veidt, he was more than capable of inheriting his father's wealth, but instead gives it all away and builds his own financial empire.
 * Batman foe Ra's Al Ghul has stubbornly clung to life for centuries via Lazarus Pits and body snatching from beyond the grave since he doesn't believe any of his children are worthy of taking over his criminal empire. He first crossed paths with Bruce Wayne because he thought he could convince Bruce to become his heir with the temptations of power (his empire) and love (his daughter Talia).
 * Scrooge McDuck eventually named Huey, Dewey and Louie as his sole heirs because (in part) the miser feared Donald would squander his fortune given the opportunity and considered Gladstone too lazy to deserve the inheritance. Not to mention Donald's (lack of) business skills.

Film

 * Dr. Evil and his son Scott in the Austin Powers films. Dr. Evil is rather disappointed that his son doesn't want to follow in his footsteps, though Scott was heading in that direction in the second movie and becomes a near copy of his father in the third..
 * The King of the Swamp Castle in Monty Python and the Holy Grail is a bluff Yorkshireman who has built the strongest castle in all England in the middle of a swamp, after several failed attempts to do so. In contrast, his son, Prince Herbert, is an anaemic weed with a penchant for show tunes; after attempting to escape from the castle by climbing from a window, the King cuts his rope, sending him to an almost certain demise.
 * Gladiator has the emperor favor Maximus over Commodus because he considers his son too corrupt for the job, wanting instead a humble reformer to take the helm. Pity one of his son's "virtues" was Ambition.
 * In Repo! The Genetic Opera, Rotti is disgusted with his children's depravity. Perhaps not so much with because they're all out of control monsters (he himself is a master manipulator and murderer) as that they aren't qualified to lead his company.
 * The title character in Yellowbeard is extremely disappointed in his son Dan for being a nice guy: he wanted Dan to be a vicious, murderous pirate like himself.
 * This the entire plot of Billy Madison. Billy wants to inherit his father's hotel chain upon the announcement of the latter's retirement, but is deemed unworthy because he's uneducated, obnoxious, an idiot, and sometimes an ass. Billy tries to remedy this by trying to complete the education he never truly received to avoid having his father hand over the reigns to corporate sleezebag Eric Gordon.
 * Subverted in Inception, where Fischer believes himself to be this in the eyes of his dying father, and the only part he could understand of his dying words was disappointed, even though he always tried his best to be like him and make him proud. The protagonists first think about using this to implant the idea that he wants to terminate the family business to get back at his father. But Eames points out that they have a much better chance at making him believe that his father regreted being such a poor example as a greedy and unethical businessman and wishing that his son doesn't become like him, and that this would motivate Fischer to break the trillion dollar monopoly the company has. Convincing him that his father was a good man deep inside and hoped his son to be a better man than he was is something Fischer would much rather want to believe than seeing his father as an evil man who despised him.

Literature

 * Rudyard Kipling's poem "The Mary Gloster".
 * In Neil Gaiman's Stardust, the king of Stormhold is highly disappointed his sons haven't all killed each other to reveal an heir before being on his deathbed. He throws the royal topaz (ruby in the film) and tells them whoever fetches it first is the new king.
 * In Terry Pratchett's The Colour of Magic, a powerful evil wizard is so concerned with this, that he becomes undead, watching over his children until one is powerful enough to beat the others.
 * In Heroes Adrift, the main characters are sent to look for a long-lost bastard descendant of the queen as an alternate heir. Both the queen and the heir end up hating this idea once they actually meet.
 * This is the reason Samwell Tarly ends up joining the Night's Watch in A Song of Ice and Fire. His dad wants a warrior and a lord for a heir, and Sam is soft-hearted boy of some obesity. When, after a long series of miscarriages and daughters, a second male heir is produced, his dad offers him a choice: join the Night's Watch, thereby forsaking all claims to land and heirs, or experience a "tragic hunting accident."
 * Jon Arryn's six-year old, sickly and mentally stunted son Robert as well. Arryn tried to arrange for the boy to be sent away to be fostered in a more healthy environment - since his mother's over-protectiveness was a factor in his inadequacy - but died before getting the chance. In response, King Robert takes away the title of the Warden of the East from House Arryn.
 * Tyrion's father Tywin Lannister tells him that he has no intention of letting him inherit, since he despises his son for his dwarfism and because his mother died giving birth to him. Tyrion is the second son of Lord Tywin, however his older brother Jaime is a member of the Kingsguard, and therefore has foresworn his rights to inherit, which Tywin is furious at him for.
 * Speaking of, the current membership of the Kingsguard itself is considered this by its veteran members. Lord Commander Selmy considers the other six utterly unworthy; Jamie for breaking his oath and the rest for their lack of skill (in his late 60s, he claims to be capable of killing the five of them as easily as a dagger cuts through cheese, and they believe him). Things go down hill once he's kicked out. Jaime replaces him as commander, and tells one of the new guard that a member he had served with prior to the start of the series would have been able to cut through the six new members "with his left hand, while taking a piss with his right."
 * Kate Blackwell struggles with finding a proper heir in Sidney Sheldon's Master of the Game.
 * Her son Tony wants to be an artist.
 * The resultant granddaughters are twins, but Alexandra has no interest in the company, and Eve is far too evil to inherit it.
 * And Another Thing introduces Constant Mown, the free-spirited, paperwork-hating, protocol-neglecting son of Prostetnic Vogon Jeltz.
 * The Shadow of the Wind has Don Ricardo, a rich industrial who thinks his son Jorge unfitted to take over his business,
 * In the first Joes World novel, the world's richest businessman decides that his children are unfit to inherit his fortune, so he has them all murdered. Then he does the same thing with all of his grandchildren. One of his great-grandchildren does prove himself suitable, by putting a hit on his great-grandfather.
 * King Valdemar's fear that one of these might take the throne resulted in the arrival of the Companions, and an immediate edit to the inheritance laws to require that the monarch of Valdemar must also be a Herald.
 * King Valdemar's fear that one of these might take the throne resulted in the arrival of the Companions, and an immediate edit to the inheritance laws to require that the monarch of Valdemar must also be a Herald.

Live-Action TV

 * On Haven Police Chief Wournos is trying various was to to get his son Nathan ready to take over for him and be able to deal with the deadly "Troubles" on his own-He aims to make his son tougher because he'll need to be.
 * Played with in an early episode of Star Trek: Deep Space Nine. Grand Nagus Zek proclaims Quark to be his successor, and promptly dies soon afterward. Quark becomes Nagus and Zek's son makes several attempts on his life so that he can usurp the title.  The successor ends up being.
 * One episode of The Twilight Zone, "The Masks," is about a group of greedy, selfish in-laws who visit a dying man only because they want a part of his large inheritance. The man gives them the condition that they can only inherit his fortune if they wear a set of hideous-looking masks until midnight. They succeed in fulfilling this condition (and as it turns out, the old man dies at the very stroke of midnight), but the man gets the last laugh on them as it turns out that the masks have permanently disfigured their faces to make them more suitable for their personalities.
 * Drives most of the plot of Downton Abbey. On the death of his heir, on the Titanic, the Earl of Grantham's estate is all set to pass to...a solicitor. Gasp. Of course, the real issue is that Grantham would much rather leave his estate to one of his actual children (but can't, because they're all girls) than to a distant relative he's never met, who could potentially throw his daughters out onto the streets with nothing when the time comes.
 * Justified has Detroit mafia don Theo Tonin and his son Sammy, a spoiled, weak-willed mob prince who hides behind his father's reputation. As Theo's son, Sammy is the logical inheritor of the crime syndicate, but neither Theo nor Quarles has a high opinion of him.

Tabletop Games

 * In the Ravenloft setting, Azalin's son Irik was considered an unsuitable successor by his Lawful Evil father due to actually being a decent guy. Azalin eventually executed his own son for rebelling against him, and with no "suitable" heir, was "forced" to become a lich.

Video Games

 * Shinji in Fate/stay night is a total loser who thinks he's a genius. Except he really does recognize that he sucks and isn't even a magus. The fun part is that the inadequate inheritor and the inheritee? lose big time to the 'substitute magus.'
 * Only in one route though. In the other two, . And, of course,.
 * In Ace Attorney, Franziska von Karma accuses Edgeworth of disgracing her father's family name due to his losses at the hands of Phoenix Wright. She's flummoxed when he doesn't care about the insult, since he's had Character Development and learned there were more important things than a perfect winning streak.
 * And because, but that issue is never really brought up.
 * And Shiki in Tsukihime is disinherited because he is extremely sick after an almost deadly accident, and even after recovering is still too bad as a result.
 * Dragon Quest VII: The current Pendragon of Gorges struggles with this, as his mother disapproves of... well, just about everything he does. Like his insistence on using the BlissRock to make their lives easier.
 * In the backstory of Team Fortress 2, Zepheniah Mann, seeing his sons Blutarch and Redmond as idiotic and incompetent, gives them both half of his empire to squabble over. The two proceed to go to war with each other via an army of mercenaries, a war that continues to the 60's.

Western Animation

 * Prince Zuko of Avatar: The Last Airbender is a prime example, right down to being shooed away with an Impossible Task while his younger, female sibling is groomed discreetly for the actual succession to Firelord. Admittedly, this had a lot more to do with the boy's failure to emulate his father's sociopathy than his relative shortfalls in skill, cunning, and levelheadedness.
 * In Kim Possible, Señor Senior, Sr. is a classic Affably Evil Villain whose greatest disappointment is his Cloudcuckoolander / Minion with an F In Evil son, Señor Senior, Jr. He is constantly lecturing his son on how a 'proper villain' must behave.
 * This doesn't seem to bother Junior all that much, however. If anything, it only annoys him. Also, it's clear that Señor Senior, Sr. loves his son and fully intends to make him his heir, he's just a little frustrated.
 * In Evil Con Carne (The segment that used to air side by side with The Grim Adventures of Billy & Mandy) Hector Con Carne's future son isn't the least bit evil, much to Hec's chagrin. Though in the end, the Card-Carrying Villain is okay with it, and naturally, the son is okay with both of his parents being on the opposite side of morality.
 * Beezy on Jimmy Two-Shoes is nowhere near the level of evil that his father Lucius wants him to be, even though he's to be the next ruler of Miseryville. He'd rather hang out with Jimmy and his girlfriend, Saffi.
 * In The Simpsons episode, Burns, Baby Burns, Mr. Burns' son, Larry, is considered to inherit Mr. Burns' fortune, but has a tough time fitting in.
 * In ThunderCats (2011), almost everyone in Thundera thinks young prince Lion-O isn't as worthy an heir to the throne as his adopted brother Tygra, since Tygra is Always Someone Better and Lion-O is viewed as eccentric for believing in the stories of "technology," and defending the supposed rights of other, lower Animals. His refusal to conform to Thundera's cultural paradigm of Might Makes Right and species dominance doesn't help his case either. It's only when Thundera is invaded that Lion-O is vindicated, and proves his worth.
 * In Top Cat and the Beverly Hills Cats, a wealthy woman left her entire fortune to her niece because she hates her other relatives. No reason for this hatred has ever been mentioned.
 * In South Park episode "Cartmanland", Eric Cartman inherited his grandmother's money. She mentioned in her will that she left her money to him because she feared her other relatives would have spent it on crack.

Web Original

 * In one Homestar Runner short, Strong Bad wonders who will take up his email-answering mantle after he dies. He's so disappointed with all the candidates that he resolves to just never die.
 * Bruce Goodkind, the richest man in the Whateley Universe and head of the mutant-hating Goodkind family, seems to be having this problem. Oldest son? Came out as a Transsexualism and left the family. Oldest daughter? Left to be a movie starlet a la Paris Hilton. Fifth kid? Probably the best choice as the inheritor, but he turned into a mutant and was kicked out of the family.

Web Comics

 * Quain'tana from Drowtales is not necessarily a villain, but has been disappointed by at least three daughters looking to succeed her before settling on Ariel

Real Life

 * JT, the crack gang leader made famous for letting grad student Sudhir Venkatesh stick around with his gang. Venkatesh writes about how, toward the end of his career, JT tried to rebuild his gang in new areas but was largely thwarted by prospective gangsters being more interested in whether they can get a new bicycle if they join the gang than in JT's dreams of power and wealth.
 * Inverted by Louis XIV and his eventual successor Louis XV. On his deathbed, Louis XIV told his young great-grandson that he would be a great king, and warned him to avoid making war as much as possible, describing it as the "ruin of the people". Unfortunately, Louis XV ignored his great-grandfather's advice (possibly because he was only four at the time) and proved to be a woefully inept king before passing the throne to the even more incompetent Louis XVI, who proceeded to run France into the ground and lose his head in the French Revolution.