My Greatest Failure



""Watson, if it should ever strike you that I am getting a little over-confident in my powers, or giving less pains to a case than it deserves, kindly whisper 'Norbury' in my ear, and I shall be infinitely obliged to you.""

- Sherlock Holmes, The Yellow Face

Nothing defines a hero better than his morals, and the biggest sympathy point can be guilt over some monumental screw-up that taught the hero to buckle down, and stop taking his job too lightly, or get too overconfident. This is sometimes related to the origin of a Superhero, but has more impact when the hero's career has otherwise been going well for a while.

From a philosophical standpoint, this makes sense--if someone wins almost all the time, as most comic book heroes do, they would be more defined by their failures than their successes. In Marvel Comics, this is sometimes a consistent psychological flaw (the "Marvel Flaw") which occasionally even prevents a hero from succeeding.

The hero will often declare "It's All My Fault" while their friends and family say "You Did Everything You Could."

The hero may recover from this. When they do, it's usually a sign they have grown, although retcons can cause an unpleasant return to status quo.

The Failure Knight has this as part of his backstory, to explain why he is so devoted to his new charge. Often produces a combination of Bad Dreams and Anxiety Dreams.

See Dead Little Sister and I Let Gwen Stacy Die for two of the more common failures. Might result in We Used to Be Friends. Often happens to heroes who fail to make amends. Can be a Career-Building Blunder. When the failure is what put the character on the path to being the current (better) person s/he is now, it's Necessary Fail. If the plot brings about an opportunity to correct or make up for their failure, you have My Greatest Second Chance.

Anime and Manga
"Kami: I should have given up being a god quite some time ago...after all, it was I who brought the fearsome evil known as Piccolo into this world. What right have I to be a god after this? What right have I to go on living?"
 * To Naruto, his not being able to save either Sasuke or Gaara is this, especially in the infamous Tear Jerker where he thinks he is useless for not being able to save either. Thankfully, Gaara gets better in the physical sense. Mentally with  however, It Gets Worse.
 * Jiraiya looks back on his life as a long series of failures, but the one that most stands out is failing to stop Orochimaru's descent into evil.
 * Kakashi views most of his life as this: he failed to save Obito and Rin, he couldn't stop Sasuke from betraying Konoha, and he couldn't be Obito's eyes.
 * Sara's post-traumatic stress syndrome for most of Soukou no Strain is only worsened when dies too.
 * In Fullmetal Alchemist, Edward Elric feels terribly guilty for pushing Alphonse to help him use forbidden alchemy to try and resurrect their mother Trisha, leading to the loss of Ed's limbs and Al's human body. It takes years before Edward gets up the courage to ask if Alphonse blames him for it, but the answer is ultimately no; Alphonse even says that he knew the risks and went along with it.
 * The Elric brothers also consider their being unable to save from, a massive failure, as well as proof that they are ultimately mere humans.
 * Yu-Gi-Oh! GX: Season 3 has been one big Greatest Failure for Judai, ironically originating from his insecurities about never failing.
 * In Rurouni Kenshin, Kenshin is still wracked with guilt over, among other things, . This is magnified in the manga's Jinchuu arc when he apparently  . He eventually recovers, though, and finds out she's still alive as a reward.
 * Kalos Eido from Kaleido Star blamed himself for more than a decade for
 * It seems that  will haunt both Luffy and Jinbei for years to come.
 * And Luffy had one not long before that --.
 * Heero Yuy from Gundam Wing, as revealed in The Movie, . This put a face on his victims and made him The Atoner until his encounters with Rebellious Princess Relena gave him something to fight for.
 * Gundam 00 has quite a lot of these: there's Sumeragi's guilt over (accidentally: she was given false intelligence), Smirnov's guilt over (indirectly)  through following his orders, and Setsuna seems to consider  as a child to be his. Then there's that whole incident with Saji and the Katharon base...
 * Mobile Suit Gundam has the Ur Example for the Gundam franchise:.
 * Mobile Suit Gundam Age has this with Flit's guilt over
 * Chichiri from Fushigi Yuugi has spent years trying to atone for the circumstances leading up to his best friend's death. This inspired him to become the calm, dedicated monk we're first introduced to when the series begins.
 * Shinichi Kudo of Detective Conan treated his greatest failure to be driving one villain of the day to death in Moonlight Sonata.
 * In Mahou Sensei Negima, Setsuna's Failure Knight nature has its roots in an incident where she tried to save Konoka from drowning, fell in herself, and both were rescued by someone else. As a result, she constantly tries to train harder so it won't happen again. Of course, Konoka doesn't hold it against her, as they were both young children when this occurred.
 * It happens again later on, with Setsuna developing a major inferiority complex after nearly being defeated by Tsukuyomi.
 * Also subverted in an awesome way in the same scene; when a very large ball-and-chain comes flying towards them, she slices it in half and doesn't even notice it... because she's beating herself up for getting weaker.
 * In Magical Girl Lyrical Nanoha A's, Admiral Graham blames himself for Admiral Clyde's death, as he was forced to destroy the Hestia with Clyde on board, at Clyde's insistence, rather than let the Book of Darkness take over the ship and use the Arc-en-ciel on the other ships.
 * Vita is haunted by an incident between As and Striker S in which, while the two were on a mission together, Nanoha was taken by surprise, injured and nearly crippled, partly the result of her having overextended herself. Vita then dedicates herself to protecting Nanoha about as much as she is dedicated to protecting Hayate.
 * Minor character Vice also has one of these: he used to be a sniper of quite a bit of skill, but he now pilots helicopters. Why? Because several years back, his little sister was involved in a hostage situation. He tried to shoot her kidnapper but missed... and hit her in the eye. Though she survived (and doesn't hold him responsible, recognizing it as an accident), he cannot forgive himself, and resolved to give up sniping.
 * At some time between Striker S Sound Stage X and Force, Subaru was involved in fighting a fire, but despite her efforts, there were many deaths. She then took a leave of absence to train, resolving to become strong and fast enough to save everyone.
 * In Bleach, Urahara's
 * In Durarara, everything Shizuo Heiwajima hates about himself can be distilled into one incident during his childhood: when he was about ten or eleven, he developed a Precocious Crush on a woman who looked out for and worried about him due to his constant injuries (unaware that they were the result of overexerting himself in violent, uncontrollable bouts of anger). One day, while walking by her store on the way home, he saw her being assaulted by Yakuza thugs. Shizuo tried to help. He screwed up. While this wouldn't be the last time he'd end up hospitalizing someone he was trying to protect (the light novels imply that this sort of thing happened constantly), it's the example that sticks with him the most.
 * In Yu Yu Hakusho,  is a Death Seeker because he felt he couldn't suffer enough after a demon killed his students.
 * The Legend of Koizumi has The Pope turn out to have unknowingly . He has, for reasons that should be blindingly obvious, regretted it ever since he learned what he had done.
 * In Sword of the Stranger, Nanashi has more or less sworn off drawing his sword. What makes this interesting is that his failure is MORAL rather then Physical..
 * In Holyland, Masaki's is  Yuu treats   this way.
 * In Puella Magi Madoka Magica,.
 * In Busou Renkin, after seven years, Captain Bravo still cannot come to terms with the Alchemist Warrior's greatest - and only - failure.
 * Dragon Ball's Kami was the one who created Demon King Piccolo, the latter being formed from the former's inner evil. As such, Kami believes that he's as responsible for Piccolo's misdeeds as much as Piccolo is;


 * Kenichi: The Mightiest Disciple:.
 * In Berserk, not being able to  and later realizing that he made a big mistake by  was Guts' greatest failure.
 * In the horror manga Presents, Kurumi recalls an incident with a young girl whose parents would give stuffed rabbit toys as a substitute for love. Kurumi takes pity on the girl and, even though she knows better, lies and says each rabbit is stuffed with her parents' love. The next morning, however, they are anything but loving, and the housekeeper tells the girl the only reason her mother had her was to replace a pet rabbit that died. The girl violently snaps, and later that night she cuts open her parents with a pair of hedge trimmers before tearing the stuffing out of the rabbit toys and stuffing into their dead bodies. It's implied she does the same thing to the housekeeper to "share" her parents love.
 * In Magic Knight Rayearth, is considered this for Hikaru, Umi and Fuu. Mostly because they powered through the entire adventure, thinking it was completely straightforward and never thought twice about questioning their mission. It's so bad that, in the anime, Hikaru accidentally creates her own Evil Twin.

Comic Books

 * Spider Man didn't stop the burglar that would shoot his Uncle Ben (in various tellings, because of spite, laziness, or arrogance); later, he was unable to prevent his girlfriend Gwen Stacy from being killed by the Green Goblin. The latter is not helped by how his using his webbing in an attempt to save her caused her neck to snap from the recoil, a fact Marvel initially attempted to gloss over but has recently admitted (through, among others, What If? - where he saves her by diving in after her instead - and Spider-Girl).
 * Batman blamed himself for the death of sidekick Jason Todd aka the second Robin. As well, some versions of the story have him blaming himself for the death of his parents. (Notably, in Batman Begins, Bruce blames himself for the death of his parents, as they encountered Joe Chill after leaving the opera because Bruce was frightened by the bat-demon characters.)
 * That's not the only form of blaming himself for his parents - in some comics versions, he convinced his mother to wear pearls to the show, and those pearls are the reason they get robbed and shot.
 * Also in that movie, Ra's Al Ghul tells Bruce that it's his dad's fault, he doesn't take it well.
 * He also blames himself for the creation of the Joker, since he knocked him in the acid, the torture of Stephanie Brown, because he lost control of Gotham during War Games, and the death of Ted Kord, by Max Lord who hijacked Batman's creation Brother Eye, to find Ted.
 * In some continuities, at least, there's also Harvey Dent, who Batman saw a a friend and ally that could really clean up Gotham in ways he himself could not - until Harvey became Two-Face.
 * For a time, he considered making Jean-Paul Valley Batman this, saying that it was done at a moment of weakness and it was a mistake.
 * At various points in his history, Superman has had the bottled city of Kandor to deal with. More recently, he's had the only time he's ever had to kill someone; this caused him to actually leave Earth for a while.
 * Of course, now that one's only sorta in continuity. Hell remembers it enough to have one (1) demon capable of trying to corrupt Superman, but the man himself doesn't remember it.
 * Nowadays, Superman also feeling really guilty of being unable to help his childhood friend, Mon-El, conquer his deadly weakness for lead and leave the Phantom Zone where he was cast into at his request as the only way to save his life.
 * During the Silver Age and the Bronze Age, Superman's biggest failure was arguably when he destroyed Lex Luthor's protoplasmic lifeform that he created as well as causing his hair to fall out when he was trying to rescue Luthor from a lab fire when they were teens. Sure it was an accident and mostly not his fault (Luthor caused the fire and Superboy had no way of knowing what was inside at the time), but it didn't help that before the fire, Superboy jokingly said he could spy on Luthor to find out what he was working on. Luthor believed Superboy destroyed his experiment out of jealousy and dedicated his life to destroying him and proving he was better. Luthor had the scientific genius to make a cure for Kryptonite as well as unshrink Kandor, so if things had gone differently, Superman would have had a lot less problems in his life and an ally against evil as well.
 * One of the third Flash's allies-turned-enemies, Zoom, acknowledged this in a twisted way. He felt the speedster required a tragic failure to be a great superhero -- even if Zoom had to make one for him.
 * Hal Jordan, the Silver Age Green Lantern, was away in space when his home city of Coast City was destroyed. He went crazy and became a villain, Parallax, dedicated to undoing the destruction through gaining cosmic power, time travel, or just rebooting the universe itself. (It was later revealed that the great failure had let an ancient evil trapped in the Central Power Battery of the Green Lantern Corps get a foothold on his mind.)
 * Additionally, John Stewart, the Bronze Age Green Lantern, had this moment with the destruction of the planet Xanshi, being way too overconfident with his power, apparently forgetting the weakness to yellow, as the bomber painted the planet-killing bomb yellow. This depressed him so much that he contemplated suicide (The Martian Manhunter thankfully prevented that, through Reverse Psychology). The end result was a guilt that would haunt him forever, and the creation of Fatality, the sole survivor of Xanshi, who was off-world at the time, who now hunts Green Lanterns as revenge.
 * Another Green Lantern, Kyle Rayner, had his mother die of an unknown fatal disease. Even when Kyle, with God-like power, tries to resurrect her, she asks to be allowed to die. During the "Sinestro Corps War" Arc.
 * That was Kyle's second My Greatest Failure. The first came early in his career when his girlfriend Alex was killed and quite literally Stuffed Into the Fridge. Up until then he thought having a super-powered ring would be fun and a lot of laughs, but when that happened, Kyle grew up pretty fast.
 * The villainous robot Ultron was supposed to be Henry Pym's greatest failure, but it never seemed to take; later, he was given much more depressing sorts of failures to worry about (such as abusing his wife, betraying his teammates, and repeatedly going insane), while Ultron eventually (for a time, anyway) became more of a ludicrous than ominous figure.
 * During his tenure on The Avengers, Kurt Busiek did a good job of finally making Ultron into a credible threat, up to and including having him wipe an entire country's population off the map. Pym's destroying the primary unit with a metal disruptor, and a subsequent character arc that involved quite literal split personalities, were supposed to finally put Pym's demons to rest and let him start growing as a character again without the existence of Ultron and his other failures to continue hindering him. Yeah... not so much. Later writers actively regressed his sanity, brought back Ultron more than once, and had him replaced by an alien who  As of the most recent Avengers stories, he's possibly even more screwed up now than he was then.
 * Blue Devil's greatest failure was making a deal with Neron (DC's ruler of Hell at the time) to gain fame as an actor in exchange for destroying an electrical substation in the desert. This resulted in the death of his best friend Marlene Bloom, whose helicopter crashed because of the blackout. This would come back to bite Blue Devil again years later when Marlene's nephew and Blue Devil's sidekick Eddie Bloomberg/Kid Devil found out after making a deal with Neron for powers. This resulted in Eddie losing his trust in Blue Devil and Eddie eventually losing his soul to Neron once he turned twenty.
 * John Constantine, Hellblazer, botched a summoning and caused a little girl to be dragged down into Hell. This hung over him for years, until he was able, thanks to some clever manipulation and trickery, to free her soul and the soul of every other child in Hell.
 * In the Marvel Universe, Captain America originally was plagued with guilt about his sidekick, Bucky, being killed when he could have spared him by not allowing him to be his sidekick. However, the writers realized how old that got and had Cap's later protégé, Rick Jones, demand he get over it and move on. Furthermore, that guilt was replaced by the writers with Cap troubled by the state of the nation, which is at least more sophisticated and flexible a concern to use. Having said that, Bucky's death still influenced his interaction with younger superheroes, notably Spider-Man.
 * His guilt came back when it turned out that Bucky survived, only to have been found by the Soviet Union and turned into the Winter Soldier; an elite assassin responsible for multiple murders. Cap considered this a fate worse then death and did his best to break his mental conditioning. Even afterwards he felt responsible for Bucky's well-being and
 * The plot of the comic series Fell is essentially watching Detective Fell right after his greatest failure, one that resulted in his banishment to his city's Shadowland, a ridiculously poor and crime-riden slum. Most of the comic so far revolves around whether the already overly intense Fell, (who may be a little too good at getting inside the head of psychos) will snap in his exile, get killed, or come out of it redeemed.
 * In Top Ten, Jeff Smax never really got over his failure to save a little princess from a dragon. Her handprint was permanently burned onto his chest, and would serve as a constant reminder of how big a screw up he was. Immediately after it happened, he informed the queen, and ran away. Across dimensions. To a world nothing at all like the one he came from. Even changing his name. Only after a necessary return to his homeworld, where the dragon was slayed and the handprint was erased, could he let it go, and even then, only a little.
 * Scrooge McDuck once frightened away an entire African tribe in an attempt to claim their land. This was the only time he ever made money dishonestly, and the resulting guilt (and zombie -- as in Bombie the Zombie) has haunted him ever since. He even became a depressed shut-in for the better part of twenty years until his nephews were able to re-ignite his spark, leading to the adventures we all know.
 * In the Sonic the Hedgehog comic, it's recently been revealed that Monkey Khan was . Understandably, he harbors massive guilt toward himself and hatred for the Iron Queen, to the point where he was angry at Knothole for holding a celebration when she had taken control of the Eggman Empire.
 * In the Fantastic Four, 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 Status Quo Is God so any changes back to a human are doomed to be short-lived.
 * Also from the Fantastic Four is the supervillain Dr. Doom. Doom built a machine that would allow him to communicate with the spirit of his dead mother, and was told beforehand by Richards that it would critically fail. But when he ignored this, that's exactly what wound up happening and left his face scarred. Years later he still can't accept that it was his fault it happened, and devotes his life to killing Richards after convincing himself he must have tampered with the machine.
 * The very different reactions of two characters who had initially been Not So Different to their respective greatest failures pretty much exemplify the fundamental difference between them: Reed acquires a long-lingering Guilt Complex and dedicates himself to With Great Power Comes Great Responsibility, which frequently torments him with It's All My Fault. Doom descends into a spiral of Green-Eyed Monster and Revenge, unrelenting in his insistence that it's Never My Fault.
 * Disproportionate Retribution indeed. In the original telling at least (Lord knows how many retcons may have flip-flopped since then) Doom didn't create the mask to hide a hideously mauled hamburger-face; he did it because the explosion left a thin, barely noticeable mar on his supposedly "perfect" facade. A man that vain, you could almost understand making some sort of covering... unfortunately in his haste, he didn't wait for the mask to cool before putting it on, which (Depending on the Writer) either DID hideously scar his face, or permanently bonded the mask to his skin. He might not admit the accident itself, but he DOES (very rarely) admit to the fact that putting the mask on so fast wasn't his smartest idea.
 * Actually all this was based on John Byrne's retcon of the Lee/Kirby origin, based on an idea by Kirby that either Stan Lee had discarded or Jack Kirby only had it after the original version was published in Fantastic Four Annual #2 (1964). There, Doom's head is completely bound up and hidden beneath bandages and in the caption Stan Lee unequivocally states: "As for Victor Von Doom... his face was hopelessly disfigured!" Also note that on the page after that, even though the mask is not completely cooled when it is put on Doom's face, it is cool enough for the monk to hold it in his bare hands (you can easily discern his fingernails etc.) By the evidence of that Annual, all the mask likely did was singe Victor's eyebrows.
 * In The Sandman, the immortal Hob Gadling will never forgive himself for having made his fortune in the slave trade.
 * Nightwing had a moment revealed following Zero Hour. When he was Robin, it was up to him to rescue Batman and the DA that replaced Harvey Dent when he became Two-Face. When he confronted the aforementioned villain, he was planning to hang the both of them for their "crimes". Two-Face attempted to hang the DA and Robin responded by cutting the line with a Batarang. However, he didn't realize that Two-Face's MO applied to everything - he saved the DA from hanging, but couldn't save him from drowning. Batman freed himself and saved the day, but the event haunted Dick until the first time he took up the Mantle of the Bat, finally making the save when confronting Two-Face again.

Film

 * Nathan Wallace from Repo! The Genetic Opera is wracked with guilt over his failure to save his wife, Marni. It's implied that her death was what caused him to become a Repo Man in the first place.
 * Implied? It's explicitly stated that Rotti used Nathan's supposed responsibility for Marni's death to blackmail him into becoming the Repo Man.
 * The Private Life of Sherlock Holmes follows Sherlock Holmes on a case which he later comes to consider one of his greatest failure.
 * Similar to the former Green Lantern example, Mr. Incredible in The Incredibles blames himself for spurning Buddy (later known as Syndrome), his biggest fan. Later, Buddy turns to evil
 * In the 2010 Continuity Reboot of The Karate Kid, Mr. Han's car accident
 * In Star Trek, Spock-prime's greatest failure was not arriving in time to save the planet Romulus from a supernova blast. This results in a mad man from the future seeking vengeance on The Federation and destroying Spock's home planet, Vulcan.
 * Averted hard in Iron Man 2, with Tony's dad appearing on some old film stating that his greatest achievement would always be Tony himself.
 * Played With in X-Men: The Last Stand, where Magneto is the one who declares that his greatest failure is that Professor X had to die before mutant equality (or superiority) could be reached.

Literature
"Bartimaeus: "It's two thousand, one hundred and twenty nine years since Ptolemy died. He was fourteen. Eight world empires have risen up and fallen away since that day, and I still carry his face.""
 * In the Redwall novel Martin the Warrior, when he blames himself and goes into self-imposed exile, setting up the events of Mossflower to which that book was a prequel.
 * Prophet's House has Sir Magnus, who lost a critical battle during a war between his patron House and its enemies. He's also The Atoner.
 * John in The Grapes of Wrath thought his wife had a stomach ache when what she really had was much more serious. He's never forgiven himself, and his every action is driven by a desire to atone.
 * Looking for Alaska's titular character  Later in the novel, most of the principle cast (including the narrator) gets their own greatest failure when   The kicker?
 * In Harry Potter and the Deathly Hallows, it's revealed that Dumbledore is wracked with guilt at his failure to  He learns from the whole thing that he ought not to be trusted with power; and it certainly seems to be his one failure.
 * It could be argued that Harry's own greatest failure comes in Order of the Phoenix, when his overconfidence and disregard of Kreacher ultimately result in.
 * In OOTP, we get a peek into Snape's "Worst Memory": an incident of bullying against Snape by James Potter and Sirius Black, which culminates in Snape calling Lily Evans a Mudblood in anger after she comes to his defense. Later, in Deathly Hallows, we find out why it's his worst memory:
 * Sniper-turned-pilot Myn Donos led the shiny new Talon Squadron into a trap, and only he and his astromech survived, through sheer luck. He's pretty much the poster child for Heroic BSOD and Defrosting Ice Sniper, blaming himself. Interestingly, while he isn't explicitly blamed by others, his instructor wonders if he is such a bad teacher that he can't teach squadrons the quick thinking and flexibility it takes to survive an ambush.
 * Donos was inducted into Wraith Squadron, known for being populated by people on their Last Second Chance. Another Wraith, Castin Donn, was a slicer in a Rebel cell on Coruscant. When they received the broadcast of the second Death Star exploding and the Emperor dying, he hacked public viewscreens to display it, since there was no way the citizens would see it without the filter of Imperial propaganda otherwise. Crowds went nuts, riots and wild celebrations ran through the streets, and in one plaza a huge statue of the Emperor was torn down... and then the stormtroopers came and fired into the crowd, killing many of them. Castin holds himself at least partially responsible.
 * Dia Passik faces her greatest failure in Iron Fist, where she is forced to shoot  during a botched infiltration job. (He was probably already dead.) She comes out of the experience both disgusted by her seeming failure and frightened of her own ruthlessness. However, her companions and superiors praise her actions, telling her that by doing what she had to do, she saved the rest of the team and their whole operation.
 * Kell Tainer has his problems with anxiety and cowardice during missions in Wraith Squadron, which he considers his own major failing, although he eventually deals with them. Given how much of a Dysfunction Junction the Wraiths are, it's not surprising these are handed out pretty liberally.
 * Sherlock Holmes often dwells on his defeat at the hands of Irene Adler in A Scandal In Bohemia, although he holds no real grudge against her. Ironically, the tale of one of Holmes' greatest failures is what first popularized him. While the first Holmes story was A Study in Scarlet, the character and his world didn't hit the big time until A Scandal in Bohemia proved to be a runaway success.
 * And as quoted above, The Yellow Face is a case where his theory about the cause of certain mysterious events proves to be quite wrong. Yes, even Sherlock Holmes makes mistakes.
 * Despite being the page quote, this case does not actually apply, as the situation turned out excellently well for all involved and the worst harm was to Holmes' pride, since the actual scenario was much Lighter and Fluffier and featured much less betrayal than he had thought. Do Not Multiply Entities Beyond Necessity!
 * He's pretty good-humoured about owning up to it, too. This is from when Doyle still liked Holmes, and didn't write him so much of a jerkass.
 * Agatha Christie did an hilarious subversion of the trope, and a very obvious Take That against the original Sherlock Holmes example just above. Hercule Poirot, the brilliant if egotist detective, retells, at Hasting's insistence, the story of his only failed case, which had involved a chocolate box. He then tells him to whisper "chocolate box" to him whenever he gets too pompous, because he tends "to get over-confident thanks to his super-human intelligence." Hastings then immediately says "chocolate box." Poirot doesn't get the joke. At all.
 * Grand Admiral Thrawn of The Thrawn Trilogy pulls off his tactical genius through the psychological insights into alien enemies he gains from studying their art. Just once, he failed to gain any insight - and he keeps the original piece of art to remind him. By the time of the trilogy he thinks he's finally starting to understand... not that it will be any help in the future. He'd had to destroy the planet. Pity.
 * Navidson's greatest failure in House of Leaves was his failure to save, a little African girl dying of starvation, and taking her picture instead. This would continue to haunt him for years.
 * Jemidon from Secret of the Sixth Magic by Lyndon Hardy is haunted by the memory of his Dead Little Sister, who wouldn't have died if the gold coin his parents gave him to pay for his test as a would-be thaumatuge had been spent on medicine instead. He failed the test, and both he and his parents blame him for her death.
 * In The Dresden Files, Harry considers half-conversion to a Red Court vampire and his inability to find a cure for her to be his greatest failure, driving him to near-poverty and a long Heroic BSOD shortly after it first happens. Years later, when he  and then learns that that act, he says that whatever number of people he saved, it will always be one too few.
 * Sisterhood series by Fern Michaels: Played with rather strangely with Henry "Hank" Jellicoe. Game Over indicates that there is one topic that he refuses to discuss, to the point that it is not even stated what the topic is. Deja Vu reveals that the topic is his wife Louise. She and her daughter left him and went under Witness Protection a long time ago, and he, with all his power, has never been able to find her. However, he had treated her like she didn't exist and was just a servant. He took phone calls on his illegal dealings, and he did it right in front of her! She kept a diary of his dealings that apparently ended up in the hands of the CIA, and he, with all his knowledge, has never been able to confirm the story. He wants to find her...and then kill her for having the nerve to go against him and leave him! Even villains can have a My Greatest Failure.
 * In Anne Mc Caffery's Damia, the title character accidentally fried the mind of her first lover. She considers it this because not only did she never consider keeping her mental guard up while with a far lower T-rating, she ignored Afra's warning to "be careful" out of spite, due to a fight they'd had earlier (After Afra had rebuffed a rather unsubtle attempt at seduction). This helped drive a wedge between herself and Afra that lasted a decade Later books showed that Damia made sure her children knew all about "the facts of life" so they wouldn't go through what she did.
 * Bartimaeus feels the death of his master Ptolemy  is this, and his guilt is so bad he wears the face of Ptolemy millennia after the boy's murder.


 * Beachwalker's protagonist had one of these in the form of  She is determined to keep the past from repeating itself, whatever the cost to herself.

Live Action TV
"Chakotay (to Tuvok): "She was working for them, you were working for her...was anyone on my ship working for me???""
 * Wesley Wyndham-Pryce from Angel committed his greatest failure when he falsely abducted Angel's only child in order to save both from demise. The prophecy which led Wes to believe this, was altered however, never meant to come true.
 * Charles Gunn's greatest failure was when he made a deal with Dr. Sparrow to make his legal upgrade permanent in exchange for signing to release an ancient curio stuck in customs. This results in the death of and resurrection of the demon Illyria. Gunn becomes so guilt-ridden, that he offers to take Lindsey's place in a hell dimension to get information to stop the Senior Partners.
 * In between the original and new Doctor Who series, the Time Lords and Daleks fought a war that annihilated both sides. The Doctor's greatest failure is letting his people die and surviving himself.
 * It is revealed in The End Of Time, the final 10th Doctor episode, that the Doctor really had no choice whatsoever..
 * Before that, The Doctor felt great guilt over not having the guts to assassinate Davros, creator of the Daleks when he had the chance.
 * . Really, the loss of any companion wounds the new Doctors deeply, and has them beating themselves up for a good while afterwards.
 * He's also convinced that he ruins his companions' lives. When the TARDIS voice interface takes his form in Let's Kill Hitler, he tells it to "give me someone I like." Holograms of Rose, Martha, and Donna are met with a response of "guilt", "also guilt", and "more guilt". He finally settles on the image of little Amelia, "before everything went wrong."
 * In Star Trek the Original Series, Captain Kirk failed to restrain his friend Commander Mitchell when he began exhibiting God-like powers, although he was warned by Mr. Spock. It wasn't until Mitchell killed a crewman and set about destroying the Enterprise that Kirk took action.
 * Likewise in Star Trek II the Wrath of Khan, Kirk's blunder in failing to arm the Enterprise in time resulted in Khan blasting the ship nearly to hell. He came back nicely though....
 * Both of these pale in comparison to Kirk's real greatest failure: he failed to save his son, David.
 * Subverted in the Star Trek the Next Generation episode "Tapestry", where what Picard thought was his worst failure was picking a fight as a cadet and getting an artificial heart due to getting his real one stabbed. As Q showed, that incident made Picard what he is.
 * Played straight in Star Trek First Contact, where Picard's real greatest failure was being unable to stop the Borg from using him as part of their invasion in "The Best of Both Worlds".
 * In Star Trek Voyager, 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.


 * One of the defining moments for Firefly's lead character, Malcolm Reynolds, was the complete, total, and utter defeat he suffered at the Battle of Serenity Valley. By the time the battle was over, he had lost his faith and had been turned from a chipper, patriotic, and energetic soldier into the tired, cynical bastard he is in the series.
 * In Babylon 5,
 * Delenn's greatest self-recognized failure was  Despite what they claim, Minbari are extremely compulsive and bloothirsty.
 * Londo Molari had two greatest failures:
 * Getting involved with Morden and his "associates" in the first place, thus kick-starting the entire Shadow war. Hell, Londo's life was one long string of incredibly bad choices, motivated by self-interest and fear. By the time he discovered he was on the wrong path and began walking the right path, it was far too late for him to save himself.
 * G'kar had at least one greatest failure: Torturing Londo and submitting him to literal Mind Rape to discover how completely Londo fistfucked the Narn people with the Shadows' help. It took Kosh's intervention to show G'kar that he would eventually fall as low as Londo had, before setting G'kar back on the path to redemption.
 * Stargate Atlantis. Rodney Mc Kay's unintended destruction of an entire solar system (well, five sixths) is brought up occasionally by Sheppard, though usually as a joke, seeing as the system was uninhabited.
 * Lt. Col. John Sheppard's is when he bombed a truck he thought was carrying enemy soldiers, but was instead carrying civilians.
 * Torchwood. Jack's inability to.
 * Jack. . This, in combination with was enough to convince him that.
 * In Homicide: Life On the Street, Detective Bayliss is haunted by his failure to solve his very first case, the murder of a little girl called Adena Watson. Although he makes numerous efforts to put it behind him, and later develops from the rookie he was when he caught the case to a competent, seasoned homicide investigator, his obsession persists throughout the entire series, even after it seems that the girl's family have moved on.
 * The case is based on the real life unsolved murder of Latonya Kim Wallace, the "Angel of Reservoir Hill", the investigation into which is covered in the book upon which the series is based. As noted in the book, the real life detective in charge of the investigation grew fixated on the case, but the epilogue stated that at time of writing he was beginning to accept it and move on.
 * Detective Monk has solved every case he has come across. However, he's been stuck for a long time on that little case of his wife Trudy being blown up by a car bomb.
 * Clark Kent has had several, including when he reversed time (a one-use only deal) to save Lana's life, only for his dad to suffer a heart attack and die at the end of the day. Also, John Corben/Metallo blames him for his turn to evil, because when Clark saved a bus from crashing, a passenger from that bus went on and murdered Corben's sister the next day.
 * 24: Jack's failure to protect from the inherent dangers of his profession.
 * In Mighty Morphin Power Rangers, failing to retrieve the Green Candle in season one, thus saving Tommy from losing his powers, was shown to have haunted Jason for a long time, to the point where he even makes reference to it in Zeo.
 * Andros. Dear Lord, Andros. First he loses his sister as a child, then his best friend Zhane is nearly killed during a battle and Andros puts him in cryogenic stasis to keep him alive.
 * Shotaro Hidari blames himself for the death of his boss, Sokichi Narumi, primarily because he ignored Sokichi's orders on a particularly dangerous job, which lead to guards chasing them and gunning Sokichi down. As a result of this and Sokichi's Famous Last Words, Shotaro lives his life trying to achieve the "hard-boiled detective" ideal his boss embodied.
 * In The X-Files, Mulder is plagued by guilt over not protecting his younger sister, Samantha, from abduction when they were children, despite the fact that it involved circumstances well beyond his control. His parents don't help assuage his guilt over it; at one point a clone claiming to be his sister is killed, and his father is upset and tells Mulder that he has to tell his mother that he lost his sister...again. As a result, he becomes obsessed with protecting Scully, especially after her abduction in season two. He ditches her several times, to her annoyance, and at times demands she stay out of a case for fear of her life. And woe is you if you're the one who hurts Scully.
 * In Warehouse 13, Myka is wracked with guilt over the death of her partner and lover, while she was in charge of the mission. For Pete, it's the death of his firefighter dad in the line of duty, when Pete decided not to tell him that he had one of his bad feelings. One episode serves to get both characters to come to terms with their respective guilts and realize they're not at fault. Myka's partner disobeyed her orders and got himself killed, while Pete's dad would've done his job no matter what his son said. Everything H.G. Wells does is because of the death of her daughter during a home invasion a century ago, while she was out of town.
 * In Warehouse 13, Myka is wracked with guilt over the death of her partner and lover, while she was in charge of the mission. For Pete, it's the death of his firefighter dad in the line of duty, when Pete decided not to tell him that he had one of his bad feelings. One episode serves to get both characters to come to terms with their respective guilts and realize they're not at fault. Myka's partner disobeyed her orders and got himself killed, while Pete's dad would've done his job no matter what his son said. Everything H.G. Wells does is because of the death of her daughter during a home invasion a century ago, while she was out of town.

Tabletop Games

 * For decades in Forgotten Realms, Drizzt Do'Urden had kept a vow to never kill another dark elf. However, he couldn't keep it forever, and in order to escape, had to kill one of his kin. He was guilt-wracked for this...but, in a possible subversion, not for long, as he realized it was a hypocritical vow, given that he had often seen the necessity of killing orcs, humans, goblins, duergar, wererats, and others who actually tended to be less Always Chaotic Evil than his own people.
 * In the Warhammer 40000 universe, the vast Imperium of Man has its own greatest failure during the end of the Great Crusade. During the beginning, it was believed that there was nothing science and reason couldn't conquer. And then they met Chaos... Horus rebelled, the Emperor died, and suddenly the Imperium became very suspicious of itself. So new measures were taken to make sure such heresy never happened again.
 * Another 40K example is Sarpedon of the Soul Drinkers, who nearly led his Chapter into the clutches of the Dark Gods...and has eight legs to remind him of the danger of Chaos.
 * The Emperor is not dead. He is the living God of the Imperium who sits upon the Golden Thrones and guides us through these trying times. To say otherwise is Heresy. Repent immediately, before I have a chance to get the Promethium.
 * Of course, this is nothing compared to the Eldar race's greatest failure, which resulted in: 1) the destruction of their galaxy spanning empire (although it was admittely decadent by that point), and the deaths of billions (if not trillions) of their race; 2) the fragmenting of the race into repressed ivory-tower ascetics, nature-attuned tribal agrarians, and blood-thirsty torture-obsessed sociopaths; and 3) the creation of one of the most powerful, and seriously messed-up Chaos gods.
 * In Exalted, this is how Green Sun Princes become Green Sun Princes. They're on the edge of a heroic, epic act that would grant them Solar Exaltation...but then they choke, and then, in their moment of weakness, despair, and regret, the Yozis are there to offer them the Deal with the Devil that grants them the Infernal Exaltation.

Toys

 * Lesovikk in Bionicle once briefly hesitated in a fight against a group of Zyglak, costing him his entire Toa Team, and driving him into a millennia spanning Heroic BSOD and Walking the Earth for ages.

Video Games
""Eventually I hope to be able to get it through their thick Spartan skulls that Thom is dead because he chose to pursue a group of enemy combatants ON HIS OWN rather than wait for backup.""
 * In Final Fantasy VII, Cloud feels regret over several failures. His  leads to Cloud suffering from psychological disorders like Trauma-Induced Amnesia and Split Personality. He also regrets failing to prevent the death of , which motivates Cloud to take down Sephiroth.
 * In the prequel Crisis Core, Zack's failure in capturing Genesis and preventing the  also fall into this category.
 * In the backstory for Halo: Reach: both Carter and Kat consider the same event, the death of their squadmate Thom, to be Their Greatest Failure. Kat planned the operation he was killed on, while Carter blames his "inadequate team preparation." However, to quote their commanding officer:


 * The Didact seems to consider his entire life to be this trope. Of particular note is his hand in nearly wiping out humanity over a misunderstanding, losing every one of his children in the effort, being defeated by the Builders in his effort to prevent and safeguard against the inevitable return of the Flood, and, to top it all off, . This guy just couldn't catch a break (except for that thousand-year coma he was forced to go into after the again-aforementioned struggle against the Builders).
 * projects this onto Phoenix Wright in Ace Attorney: Trials and Tribulations, feeling that  is Phoenix's greatest failure. It's a cover for blaming himself.
 * Detective Badd of Investigations wears a bullet-riddled trenchcoat to remind himself of his failure to protect Cece Yew from being murdered by a smuggling ring before she could testify. This also led him to
 * In Tales of Symphonia, Lloyd and Genis are most troubled by the mutation and death of their friend Marble after Lloyd had been caught sneaking into the ranch to visit her with Genis, which also led to an attack on Iselia. It's made worse when her granddaughter Chocolat refuses to be rescued after learning this.
 * Sheena is also burdened by her failure to make a pact with Volt, even though she was unable to understand what he was saying and (unbeknownst to her at the time), he no longer wanted to make a pact.
 * Kratos has at least two of these, both spoilery:
 * In Metroid: Other M, Samus's falling out with Adam is implied to be a result of her greatest failure. The incident in question turns out to be.
 * Pick a BioWare game, and chances are you'll hear one of these from at least one of your party members. Chances are, you'll end up with them when they attempt to correct said failures, too.
 * A more comprehensive list:
 * In Mass Effect, Garrus was rather angry about an organ farmer that C-Sec's regulations prevented him from stopping. His personal mission in that game is to hunt down and kill the organ farmer.
 * In Mass Effect 2, you recruit Garrus from the battlefield in which most of his team was slaughtered. His loyalty mission is to hunt down the man that sold them out.
 * Also in Mass Effect 2 is Thane's regret that he left his son behind following his vengeance on his wife's murderers. His loyalty mission is to keep Kolyat, the son in question, from following in his footsteps.
 * While Samara cannot be blamed for having daughters who are Ardat-Yakshi, Asari with a rare genetic disease that makes them addicted to murdering people by draining their life energy, she later makes it her life's mission to hunt down and destroy Morinth, the daughter who ran to preserve her freedom rather than join her sisters in isolation at a remote monastary where they learn to supress their urges and are far removed from any temptations.
 * In Mass Effect 3, being forced to leave Earth in the midst of a Reaper invasion is this for Shepard
 * In the same game,
 * In Jade Empire, Sagacious Zu regrets his failure to save Master Li's family from the Emperor's vengeance. You learn later that.
 * In Dragon Age, Wynne was assigned to mentor a young elven mage during her younger days, and he ended up fleeing the Circle and getting killed by the Templars..
 * Sten considers losing his sword to be his greatest failure. Swords are very important to the Qunari.
 * Oghren also blames himself for his entire clan dying and his wife Branka going insane, believing that had he been a better husband she may have not gone on her mad quest for the Anvil of the Void and dragged their clan into their gruesome fate.
 * In Knights of the Old Republic, Carth considers his failure to stop Admiral Karath from turning on the Republic to be his greatest failure; about three-quarters of the way through the game he gets to kill the Admiral.
 * In Neverwinter Nights, the confused angsty mess of a person that is Aribeth considers her fiancee's unjustified execution at the end of chapter 1 to be her failure.
 * In the Sam & Max game The City that Dares Not Sleep,
 * In Metal Gear Solid 4  views the killing of his mentor and friend who taught him everything he ever knew as a soldier and then going on to fight for causes that she never would have believed in as his greatest failure. He goes so far as to claim after that point he was already dead emotionally. At the end of Metal Gear Solid 4 as he stands above her grave   proclaims to his son that if he had been in his place he probably wouldn't have made the same mistakes and that he still has a chance to do things better than he ever had.
 * In Okami, when, he didn't realise that  was on board, leading to the   getting slaughtered.
 * Goenji Shuuya (Axel Blaze) in Inazuma Eleven blames himself for his sister's serious accident a year before the game's event because playing a national soccer tournament  put his sister into a coma, but is snapped out of a Wangst state by The Hero's Hot Bloodedness. Then he is determined to win a Football Frontier tournament for his sister.
 * In Persona 3, one of the things The Answer deals with is Aigis's Greatest Failure. That is,
 * In Tales of the Abyss, Jade's backstory includes having accidentally killed his teacher with experimental magic as a child. He's mostly gotten past it now, but it drove him to extreme lengths trying to make a Replacement Goldfish for about ten years until Peony knocked some sense into him.
 * According to the original backstory, Serious Sam was the captain of the starship that drew Mental's attention to humanity and he threw himself headlong, even suicidally, into the fighting to try and atone.
 * Ethan Mars from Heavy Rain believes that his his son Jason's death was his fault, and seems to suffer some degree of PTSD as a result.

Web Comics

 * In El Goonish Shive, Grace cowered as Damien went on a killing spree breaking her and her brothers out of the lab that created them. Grace later finds out that she was created to fight Damien, and her guilt over failing to act the first time overcomes her pacifistic tendencies and drives her berserk when Damien threatens to kill Nanase and Ellen. Despite saving her friends' lives and freeing her brothers by defeating Damien, she feels even more guilty for losing control and then failing to keep him from committing suicide. This hat trick of perceived failure leads her to swear off using her shapeshifting powers until her sister and grandfather convince her to stop blaming herself.
 * Vaarsuvius from Order of the Stick is a highly intelligent elven wizard with a large ego. That ego takes a severe beating when the elf is unable to defeat a highly spell-resistant death knight, fails to prevent the hobgoblins from overrunning the breach at Azure City and winning the battle (including having fleeing allied soldiers beg him/her to help them and one of them cursing the elf's "useless goddamn magic" with her dying breath after V is unable to help them due to having run out of spells), and then spends months trying to overcome the effects of an anti-scrying abjuration without luck, in a situation when the fate of the world practically hinges on the elf's success. The long-term consequences for Vaarsuvius remain yet to be revealed, but in the short term, they certainly include Bad Dreams, every symptom in the book for Post Traumatic Stress Disorder, and easy temptation to a Face Heel Turn when his/her self-perceived lack of ability puts his family in danger.
 * Elan gets a bit of this when the half-orc Therkla is killed trying to protect him. She's poisoned, and Elan lacked the Bard spell that would have cured her. It affects Elan enough that when he reunites with Haley, he reveals that he took "Neutralize Poison" at his next level up.
 * Homestuck: Even after 413 years, WV still won't let himself forget that

Web Original

 * In Survival of the Fittest, Adam Dodd doesn't only have one of these, but two. The first of these is allowing himself to become separated from the other members of his group - among them his girlfriend and other close buddies of his. . Adam, of course, blames himself for this. His second stems from an incident where his (mentally unstable) brother attacked him. Adam regrets throughout version 1 his failure to forgive his older brother.
 * In Greek Ninja, Sasha fails to save her sensei during the invasion of Ariadnio.

Western Animation

 * Number 5 of Codename: Kids Next Door blames herself for some Noodle Incident where the Delightful Children made Number 1 bald and sees an opportunity to save a random girl from the Delightful Children as My Greatest Second Chance.
 * In the third season of Transformers Generation 1, Optimus Prime's successor, Rodimus Prime (formerly Hot Rod) doubted his abilities to fill Optimus's shoes, in part because during Optimus's last stand, Hot Rod tried to join the battle and help, only to wind up being used as a hostage/shield by enemy leader Megatron--had Hot Rod not stepped in, Prime may have survived. Visiting Prime on his deathbed, Rodimus asked for forgiveness... But Prime slipped away before he could forgive Rodimus.
 * Although he did
 * Aang's loss to Azula in the second season finale of Avatar: The Last Airbender, resulting in not only the loss of the entire Earth Kingdom but Aang's death as well. Cue Aang stealing Zuko's "I must restore my honor" speech when he gets better.
 * Justifiably, since he thought it possible he'd lost the Avatar State FOREVER.
 * He expresses a similar regret over running away, feeling that he's responsible for the escalation of the war and the destruction of the Air Nomads.
 * Several other characters, however, say that running away was beneficial, even fateful, in the long run. After all, if he hadn't run, he would've just been another 12-year-old body in the massacre of the air nomads -- but by spending a hundred years out of time, he becomes the Right Man in the Wrong Place.
 * Aang's predecessor, Avatar Roku, had several opportunities to stop his best friend Fire Lord Sozin from starting the hundred-year war in the first place. Sozin expresses to Roku that maybe he should Take Over the World to share the "greatness" of the Fire nation? Roku, without even, you know, explaining to Sozin just why this would be a terrible idea, just blows him off and says forget it. Sozin sets up colonies in the Earth Kingdom? Roku fights him off but doesn't kill him, incarcerate him, warn the Earth Kingdom and the Water Tribes of his leanings, or anything beyond telling Sozin "never try this again or else". Is there any surprise at Sozin's dick move in ? Naturally,, both regret what happened.
 * A side-story, shown as motion comics, gives Avatar's Kyoshi and Kuruk one of these. Kyoshi formed the Dai Li, which went on to assist an Evil Chancellor from turning Ba Sing Se into a totalitarian city-state which carried after Azula conquered it. Kuruk wasn't a good Avatar, spending most of his time impressing people with his bending prowess. But when he found a wife and started shaping up, Koh the Face-Stealer snatched her, possibly to punish him.
 * For Uncle Iroh, it's his failed seige of Ba Sing Se during his time as a Fire Nation general. It's hinted many times that the failure isn't because of the military disgrace, but because he lost his son in the battle.
 * In Transformers Prime, Arcee takes the deaths of her partners  very personally. Whenever either of them comes up in conversation, her normally assertive confident personality slips into rage, and the possibility of it happening again turns her into a nervous self-doubting train wreck of a person.
 * Ratchet greatly regrets  along with his life.
 * Lao Shi, Jake's grandfather and trainer in American Dragon Jake Long, became much more focused and wise when he nearly got killed by the Dark Dragon.
 * Princess Celestia from My Little Pony Friendship Is Magic seems to feel this way about being forced to imprison her own little sister, Luna, in the moon when Luna became Nightmare Moon. Luna, after being redeemed, seems to feel this about becoming Nightmare Moon in the first place. At one point of "Luna Eclipsed", she's seen looking forlornly at the statue of her evil self and has become The Atoner.