History Main / MyGreatestFailure

* ''Manga/BusouRenkin'': after seven years, Captain Bravo still cannot come to terms with the Alchemist Warrior's greatest - and only - failure [[spoiler:where a school was destroyed and devoured by homunculi, save for one girl: ActionGirl Tokiko]].

* ''Fanfic/LovedAndLost'': Celestia, The Mane Five, Shining Armor, and Spike express deep regret over mistreating Twilight and inadvertently causing the Changeling invasion. This motivates them to return to Canterlot so that they can [[MustMakeAmends clear their names and make amends]].

* Speaking of Spider-Man, for his foe J. Jonah Jameson, it was definitely the Scorpion. Jonah paid private eye [=MacDonald=] Gargan to undergo an experiment that would make him strong enough to subdue and defeat the hero. The scientist conducting the experiment warned both of them that he "didn't know how it will affect your brain" but they went ahead with it anyway; true to the scientist's fears, Gargan was driven insane, becoming more of a threat than Spider-Man could ever become. Jonah has never even tried to blame this on Spider-Man (at least in any convincing way); after the Hobgoblin tried to blackmail Jonah about Gargan, the publisher has taken full responsibility for the villain, and to this day, pays for Gargan's psychiatric treatment out of his own pocket and orchestrates compensations funds to aid victims of the villain's crimes. And to make it worse for Jonah, Gargan hates him even more than he hates Spider-Man for what happened to him.

** Commissioner Gordon has his role in the creation of [[EvilCounterpart the original Wrath]]: The same night Bruce's parents were murdered, a rookie Gordon got into a firefight with a couple who'd bought their son along as they committed a crime, which ended with a wounded Gordon killing the parents in self-defense, which in-turn led to the kid becoming the Wrath. ''Batman Confidential'' # 13-16 added to this, revealing that one: the original Wrath's father was among the many {{corrupt cop}}s in the GCPD, two: a then-Captain [[ComicBook/BatmanYearOne Gillian Loeb]] covered it up to save his ass and those of the other corrupt officers, and three: Loeb forced Gordon to comply with this and a transfer to Chicago by threatening the kid's life.

* ''WebAnimation/{{RWBY}}'': Jaune Arc is hitted hard with that. He blames his own weakness and inability to stop [[StarCrossedLovers Pyrrha]] from fight Cinder as the reason why Pyrrha dies. Not be able to recognize that Pyrrha was actually in love for him made that worse to Jaune. It takes until Volume 6 to Jaune forgives himself, but he still misses her and mourns her absence. Part of his current armor and weapons are made to honor Pyrrha's memory.

* In the ''ComicBook/FantasticFour'', Reed Richards' own miscalculation and arrogance are what led to the titular team being hit by gamma rays and given superpowers. In the case of Reed, Sue, and Johnny, this is no big deal. But Ben's powers leave him a freakish rock monster, and being trapped like that put a huge barrier between the two of them for years, in spite of being best friends. It wouldn't have been so bad if Ben could just change back from being The Thing, but StatusQuoIsGod so any changes back to a human are doomed to be short-lived. The fact that Reed is responsible for his friend's condition and cannot permanently cure him is something that has weighed heavily upon him his entire career. [[spoiler:When the team finds out that their transformation was caused by the ruler of a planet who was scared of their arrival and tried to force them back, Ben goes on a RoaringRampageOfRevenge because he realized that he'd blamed the wrong guy all along.]]

* ''Series/StarTrekPicard'': Hugh is responsible for the well-being of the former Borg drones on the Artifact, so when about a dozen of them are slain by Narissa and her guards, he feels guilty that he was unable to shield them from the cruelty of the Romulan Free State.

* In ''Series/StarTrekVoyager'', Chakotay failed to catch (and ended up falling in love with) the Cardassian spy Seska in his Maquis cell, which came back to haunt him when she betrayed the series' titular ship and its crew to the evil Kazon. To add insult to injury, he also failed to catch the ''Federation'' spy Tuvok, compounding the guilt over Seska's betrayal. He only (sorta) recovered when he realized that ''neither'' spy realized the other was in the cell, making the incident not (entirely) his fault.

** Della Duck and the ''Spear of Selene'' was this to Scrooge. He had a made a special surprise for Della Duck; a rocket known as the ''Spear of Selene''. No one knew about it because Scrooge told no one about this secret little project he had in the works. Unfortunately, Della had this knack for digging into things she's not supposed to be digging into, and to make matter worse, the rocket wasn't even properly tested. Della hijacked the rocket and took it for a ride in orbit, one which seemingly proved to be her last. Scrooge tried to guide Della through the cosmic storm, only for lightning to hit the ''Spear of Selene'', causing the rocket to lose contact with Scrooge and [[spoiler: ironically force Della to crash on the moon]]. Scrooge was willing to go as far as to bankrupt himself, trying to find her somewhere lost in outer space only for same event to likely befall his crew. The search for Della wound up costing him millions, if not ''billions'', of dollars and because it was proving fruitless, he was ultimately forced to cancel the search for Della by his staff. Until the events of ''Woo-oo!'', Scrooge had more or less become a shut-in and had never spoke to his family after what happened to Della.

* ''Fanfic/MyHeroSchoolAdventureIsAllWrongAsExpected'': Hachiman regrets losing contact with [[OnlyFriend Zaimokuza]] after entering high school and never thanking him for letting him copy his HealingFactor Quirk, especially after learning that [[spoiler:Zaimokuza went missing and [[UncertainDoom likely died]] without Hachiman finding out until it was too late]]. This is the reason why he goes out of his way to be nice to Saki Kawasaki, another student who (albeit unwittingly) provided him with a Quirk essential to his heroic lifestyle. This is also why Hachiman is so determined to do everything he can in the U.A. Sports Festival to earn helself a spot on Hiratsuka's investigative team as they look into [[spoiler:Zaimokuza's disappearance]].

* ''WebAnimation/{{RWBY}}'': Jaune Arc is hitted hard with that. He blames his own weakness and inability to stop [[StarCrossedLovers Pyrrha]] from fight Cinder as the reason why Pyrrha dies. Not be able to recognize Pyrrha was actually in love for him made that worse to Jaune. It takes until Volume 6 to Jaune forgives himself, but he still misses her and mourns her absence. Part of his current armor and weapons is made to honor Pyrrha's memory.

* ''WebAnimation/{{RWBY}}'': Jaune Arc is hitted hard with that. He blames his weakness and inability [[StarCrossedLovers to stop Pyrrha]] from fight Cinder as the reason why Pyrrha dies. Not be able to recognize Pyrrha was actually in love for him made that worse to Jaune. It takes until Volume 6 to Jaune forgives himself, but he still misses her and mourns her absence. Part of his current armor and weapons is made to honor Pyrrha's memory.

* ''WebAnimation/{{RWBY}}'': Jaune Arc is hitted hard with that. He blames his weakness and inability [[StarCrossedLovers to stop Pyrrha]] from fight Cinder as the reason why Pyrrha dies. Not be able to recognize Pyrrha was actually in love for him made that worse. It takes until Volume 6 to Jaune forgives himself, but he still misses her and mourns her absence. Part of his current armor and weapons is made to honor Pyrrha's memory.

* Asha al'Wahim's ancestor from the ''Franchise/MassEffect''[=/=]''Franchise/AvatarTheLastAirbender'' crossover ''FanFic/AvatarOfVictory'' was actually a pretty good general, until he made a mistake during the First Contact War that got the previous Avatar killed. As such, her entire family is considered jinxed, and she takes it upon herself to [[TheAtoner try and regain some of her family honor]].

* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, with the Project itself destroying the other Freelancers' lives over time during its ruinous slog of development of its AI Fragments during the years of its activity. she definitely feels multiple ripples of this '''BIG time''' after many of her former comrades died, earning the eternal vengeance of a inferno-obsessed pyromaniac and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him vengefully haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the other surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating on her past-self a very great deal.]] ]]

** It's revealed in ''Literature/HarryPotterAndTheDeathlyHallows'' that Dumbledore is wracked with guilt at his failure to [[spoiler:take care of his little sister, whom both of his parents died to protect. He instead chooses to run around with Grindelwald [[FantasticRacism espousing anti-Muggle ideals]]; and she is accidentally killed during a fight they have]]. He learns from the whole thing that he ought not to be trusted with power; and it certainly seems to be his one failure. He straight-up tells Leta Lestrange (to whom a very similar thing happened) in ''Film/FantasticBeastsTheCrimesOfGrindelwald '' that it’s his biggest regret in life.

** It's revealed in ''Literature/HarryPotterAndTheDeathlyHallows'' that Dumbledore is wracked with guilt at his failure to [[spoiler:take care of his little sister, whom both of his parents died to protect. He instead chooses to run around with Grindelwald [[FantasticRacism espousing anti-Muggle ideals]]; and she is accidentally killed during a fight they have]]. He learns from the whole thing that he ought not to be trusted with power; and it certainly seems to be his one failure.

* In the ''ComicBook/FantasticFour'', Reed Richards' own miscalculation and arrogance are what led to the titular team being hit by gamma rays and given superpowers. In the case of Reed, Sue, and Johnny, this is no big deal. But Ben's powers leave him a freakish rock monster, and being trapped like that put a huge barrier between the two of them for years, in spite of being best friends. It wouldn't have been so bad if Ben could just change back from being The Thing, but StatusQuoIsGod so any changes back to a human are doomed to be short-lived. The fact that Reed is responsible for his friend's condition and cannot permanently cure him is something that has weighed heavily upon him his entire career.

* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, with the Project itself destroying the other Freelancers' lives over time during its ruinous slog of development of its AI Fragments during the years of its activity. she definitely feels multiple ripples of this '''BIG time''' after many of her former comrades died, earning the eternal vengeance of a infero-obsessed pyromaniac and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him vengefully haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the other surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating on her past-self a very great deal.]] ]]

* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, with the Project itself destroying the other Freelancers' lives overtime during its ruinous slog of development of its AI Fragments during the years of its activity. she definitely feels multiple ripples of this '''BIG time''' after many of her former comrades died, and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him vengefully haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the other surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating on her past-self a very great deal.]] ]]

* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, she definitely feels this '''BIG time''' after many of her former comrades died, and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him vengefully haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the other surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating on her past-self a very great deal.]] ]]

* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, she definitely feels this '''BIG time''' after many of her former comrades died, and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him vengefully haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating on her past-self a very great deal.]] ]]

* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, she definitely feels this '''BIG time''' after many of her former comrades died, and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating on her past-self a very great deal.]] ]]

* Agent Carolina from Machinima/RedVsBlue is this in SO many spades over her previous [[CompetitionFreak overly-competitive]] nature to please her disconnected father so long ago, where she had a great many opportunities to drive off her self-destructive path of proving herself to Project Freelancer, she definitely feels this '''BIG time''' after '''many''' of her former comrades died, and seemingly forgets a time she accidentally killed a '''very''' dear friend of a Simulation Trooper, thus having him haunt her later on in the future and giving her a VERY '''[[WaxMuseumMorgue horrific]]''' view of what happened to the surviving agents leftover from the disbanded Project Freelancer. She especially gives [[spoiler: a past version of herself a '''very scathing''' "talk" involving her aforementioned self-destructive victory-obsessed-self, essentially [[IHatePastMe hating her past-self a very great deal.]] ]]