Follow TV Tropes

Following

History MyGreatestFailure / Literature

Go To

OR

Is there an issue? Send a MessageReason:
None

Added DiffLines:

* ''ComicBook/PrimalWarriorDracoAzul'': In the short story "Reminiscence", Ekchuah reveals to Eric that his greatest failure was a battle with the Mesoamerican FeatheredSerpent god K'uk'ulkan[=/=]Quetzalcoatl that ended disastrously--costing the lives of countless innocents and destroying the city of Teotihuacan in the process.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* ''Literature/TheHypnotists'': Avery Quackenbush, a dying billionaire who hires Jax to help his medical team in ''Memory Maze'', has a lot of deep-seated trauma that traces back to being unable to save his brother from drowning during a boating accident, a memory which he's worked hard to repress by imagining his brother participating in all of his successes.
Is there an issue? Send a MessageReason:
None


* ''LightNovel/TheUnexploredSummonBloodSign'': Kyousuke is driven to save people because he sees himself as bearing half the responsibility for [[CrapsackWorld the current state of the world]]. The exact reasons for this are outlined in the first book, and further elaborated on the fifth. [[spoiler:In the past, he summoned [[TopGod the White Queen]] into the world, and she fell in love with him at first sight. After interacting with her, he decided to try and use her power to help solve the problems in the world. However, others tried to gain control of the White Queen, enraging her and causing her to kill many people. The loss of so major important leaders resulted in the chaotic state of the present world. On top of that, the White Queen is now driven to make him love her again, [[{{Yandere}} at any cost]]]].

to:

* ''LightNovel/TheUnexploredSummonBloodSign'': ''Literature/TheUnexploredSummonBloodSign'': Kyousuke is driven to save people because he sees himself as bearing half the responsibility for [[CrapsackWorld the current state of the world]]. The exact reasons for this are outlined in the first book, and further elaborated on the fifth. [[spoiler:In the past, he summoned [[TopGod the White Queen]] into the world, and she fell in love with him at first sight. After interacting with her, he decided to try and use her power to help solve the problems in the world. However, others tried to gain control of the White Queen, enraging her and causing her to kill many people. The loss of so major important leaders resulted in the chaotic state of the present world. On top of that, the White Queen is now driven to make him love her again, [[{{Yandere}} at any cost]]]].
Is there an issue? Send a MessageReason:
None


** Creator/AgathaChristie did a hilarious subversion of the trope, and a very obvious TakeThat against the original Sherlock Holmes example just above. Literature/HerculePoirot, the brilliant if egotist detective, retells, at [[TheWatson Hasting's]] insistence, the story of his only failed case, which had involved a poisoned chocolate box. He then tells him to whisper "chocolate box" to him whenever he gets too pompous, adding, "I, who have undoubtedly the finest brain in Europe at present, can afford to be magnanimous." Hastings then immediately says "chocolate box." Poirot doesn't get the joke. At all.

to:

** Creator/AgathaChristie did a hilarious subversion of the trope, and a very obvious TakeThat against the original Sherlock Holmes example just above. Literature/HerculePoirot, the brilliant if egotist detective, retells, at [[TheWatson Hasting's]] insistence, the story of his only failed case, which had involved [[Literature/PoirotInvestigates a poisoned chocolate box.box]]. He then tells him to whisper "chocolate box" to him whenever he gets too pompous, adding, "I, who have undoubtedly the finest brain in Europe at present, can afford to be magnanimous." Hastings then immediately says "chocolate box." Poirot doesn't get the joke. At all.
Is there an issue? Send a MessageReason:
None


** Creator/AgathaChristie did a hilarious subversion of the trope, and a very obvious TakeThat against the original Sherlock Holmes example just above. Literature/HerculePoirot, the brilliant if egotist detective, retells, at [[TheWatson 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, adding, "I, who have undoubtedly the finest brain in Europe at present, can afford to be magnanimous." Hastings then immediately says "chocolate box." Poirot doesn't get the joke. At all.

to:

** Creator/AgathaChristie did a hilarious subversion of the trope, and a very obvious TakeThat against the original Sherlock Holmes example just above. Literature/HerculePoirot, the brilliant if egotist detective, retells, at [[TheWatson Hasting's]] insistence, the story of his only failed case, which had involved a poisoned chocolate box. He then tells him to whisper "chocolate box" to him whenever he gets too pompous, adding, "I, who have undoubtedly the finest brain in Europe at present, can afford to be magnanimous." Hastings then immediately says "chocolate box." Poirot doesn't get the joke. At all.
Is there an issue? Send a MessageReason:
None


* [[CormoranStrikeNovels Cormoran Strike]] is haunted by the time he fractured the skull of a major who had been sexually abusing his stepdaughter. Afterwards his superiors killed the case, to avoid a police brutality scandal, and the major was allowed to leave the army and disappear - still together with the wife and stepdaughter.

to:

* [[CormoranStrikeNovels Former military policeman [[Literature/CormoranStrikeNovels Cormoran Strike]] is haunted by the time he fractured the skull of a major who had been sexually abusing his stepdaughter. Afterwards his superiors killed the case, to avoid a police brutality scandal, and the major was allowed to leave the army and disappear - still together with the wife and stepdaughter.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* [[CormoranStrikeNovels Cormoran Strike]] is haunted by the time he fractured the skull of a major who had been sexually abusing his stepdaughter. Afterwards his superiors killed the case, to avoid a police brutality scandal, and the major was allowed to leave the army and disappear - still together with the wife and stepdaughter.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* ''Literature/HiveMind2016'': Kareem's greatest failure wasn't the failed strike that killed seventeen people. It was quitting as tactical commander afterwards, putting someone less skilled into the role. He estimates that hundreds of people died because of that.
Is there an issue? Send a MessageReason:
Up To Eleven is a defunct trope


** In ''Fall of Damnos'', Scipio keeps flashing back to an attack of Nurglite cultists, when he failed to stop [[spoiler:the daemon from possessing Chaplain Orad, thus holding himself responsible for deaths of two of his squadmates]]. This leads him to become a perfectionist [[UpToEleven by Space Marine standards]], and when more squadmates die to the Necrons he's having trouble accepting it truly isn't his fault this time.

to:

** In ''Fall of Damnos'', Scipio keeps flashing back to an attack of Nurglite cultists, when he failed to stop [[spoiler:the daemon from possessing Chaplain Orad, thus holding himself responsible for deaths of two of his squadmates]]. This leads him to become a perfectionist [[UpToEleven by Space Marine standards]], standards, and when more squadmates die to the Necrons he's having trouble accepting it truly isn't his fault this time.
Is there an issue? Send a MessageReason:
None


* Twenty years before the events of ''Literature/TheSharingKnife'' books, as he faced the creatures of a powerful [[EldritchAbomination Malice]] during what became known as the Battle of Wolf Ridge; Patrol Leader Dag Wolverine lost all but three of his joint command, his left hand, his ''wife'', and [[ArsonMurderAndJaywalking the ridge in question]] in the space of an hour[[note]](the successful delaying action aspect that facilitated the death of the Malice in question was cold comfort)[[/note]]. Heroic Songs and Epic Poems have been composed since, and Patroller Dag [[TheMaidenNameDebate Redwing]] tends to slip out the back when the younger generation of Lakewalkers start in on them.

to:

* Twenty years before the events of ''Literature/TheSharingKnife'' books, as he faced the creatures of a powerful [[EldritchAbomination Malice]] during what became known as the Battle of Wolf Ridge; Patrol Leader Dag Wolverine lost all but three of his joint command, his left hand, his ''wife'', and [[ArsonMurderAndJaywalking the ridge in question]] in the space of an hour[[note]](the successful delaying action aspect that facilitated the death of the Malice in question was cold comfort)[[/note]]. Heroic Songs and Epic Poems have been composed since, and Patroller Dag [[TheMaidenNameDebate Redwing]] [[TookTheWifesName Bluefield (ne Redwing)]] tends to slip out the back when the younger generation of Lakewalkers start in on them.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* ''Literature/BazilBroketail'': Not necessarily ''the'' greatest, but in retrospect Relkin thinks he failed by falling in love with Lumbee, and most importantly having sex with her. It's not that they parted on bad terms later -- he just feels that by doing so, he betrayed the trust of his one true love Eilsa. To his credit, he wasn't ''quite'' sure whether he'll ever return to Argonath at the time and he knew that he and Lumbee are too different to have a child.
Is there an issue? Send a MessageReason:
None


* Jemidon from ''Secret of the Sixth Magic'' by Creator/LyndonHardy 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 [[spoiler:... which is ''insane'', because he was only ten when his folks urged him to get tested, and they're the ones who'd set ambition for one child above the life of another]].

to:

* Jemidon from ''Secret of the Sixth Magic'' ''Literature/SecretOfTheSixthMagic'' by Creator/LyndonHardy 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 [[spoiler:... which is ''insane'', because he was only ten when his folks urged him to get tested, and they're the ones who'd set ambition for one child above the life of another]].
Is there an issue? Send a MessageReason:
None

Added DiffLines:

** In the book ''Literature/{{Shatterpoint}}'', Mace Windu muses on how his greatest failure happened in ''Film/AttackOfTheClones'', where he had Count Dooku within arm's reach of him and decided to try to threaten him rather than kill him in a surprise attack. While it would have led to his death at the hands of Jango, it would have ended the war in an instant, which would be well worth sacrificing his life.

Added: 103

Changed: 10

Is there an issue? Send a MessageReason:
None


%%%
%%
%% This page has been alphabetized. Please add new examples in the correct order. Thanks!
%%
%%%

----



** Prior to the story's beginning, an unnamed man lost everything he had to a financial crash. Upon pleading with the bank to help him, the callous bank owner coldly blamed him just for giving the bank his money in the first place. Shortly after, the man committed suicide. Years later, the bank owner--Zara--may still seem cold and cruel on the outside, but she's been carrying the guilt of this for years. She keeps the man's suicide note to her unopened in her purse just as a reminder. [[spoiler:Though in the end, we discover the message: "It wasn't your fault."]]

to:

** Prior to the story's beginning, an unnamed man lost everything he had to a financial crash. Upon pleading with the bank to help him, the callous bank owner coldly blamed him just for giving the bank his money in the first place. Shortly after, the man committed suicide. Years later, the bank owner--Zara--may owner -- Zara -- may still seem cold and cruel on the outside, but she's been carrying the guilt of this for years. She keeps the man's suicide note to her unopened in her purse just as a reminder. [[spoiler:Though in the end, we discover the message: "It wasn't your fault."]]



** In the original novelization of the first ''Star Wars'' movie, Obi-Wan Kenobi speaks of Darth Vader as "One of my brightest pupils...One of my greatest failures".

to:

** In the original novelization of the first ''Star Wars'' movie, Obi-Wan Kenobi speaks of Darth Vader as "One of my brightest pupils... One of my greatest failures".



** Grand Admiral Thrawn of ''Literature/TheThrawnTrilogy'' 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 [[EarthShatteringKaboom destroy the planet]]. Pity.

to:

** Grand Admiral Thrawn of ''Literature/TheThrawnTrilogy'' 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 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 [[EarthShatteringKaboom destroy the planet]]. Pity.



* In ''[[Literature/EddieLaCrosse The Sword-Edged Blonde]]'', Eddie is haunted by... well, several things, but the biggest is the time he let his girlfriend (a princess, no less) be attacked and killed by a band of thugs. Most people think his failure was just not being able to protect her, but it turns out his culpability was greater than that — Eddie [[spoiler:was actually the one who escalated the confrontation to violence, out of pride and desire to impress his girlfriend]].

to:

* In ''[[Literature/EddieLaCrosse The Sword-Edged Blonde]]'', Eddie is haunted by... well, several things, but the biggest is the time he let his girlfriend (a princess, no less) be attacked and killed by a band of thugs. Most people think his failure was just not being able to protect her, but it turns out his culpability was greater than that -- Eddie [[spoiler:was actually the one who escalated the confrontation to violence, out of pride and desire to impress his girlfriend]].
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* ''Literature/AnxiousPeople''
** Prior to the story's beginning, an unnamed man lost everything he had to a financial crash. Upon pleading with the bank to help him, the callous bank owner coldly blamed him just for giving the bank his money in the first place. Shortly after, the man committed suicide. Years later, the bank owner--Zara--may still seem cold and cruel on the outside, but she's been carrying the guilt of this for years. She keeps the man's suicide note to her unopened in her purse just as a reminder. [[spoiler:Though in the end, we discover the message: "It wasn't your fault."]]
** The very same suicidal man was spotted by a teenage boy named Jack. He tried to talk him out of it, and said everything he was "supposed to," but ultimately failed. He cannot accept that it wasn't his fault, and years later, as a police officer, the guilt of not saving the man fuels him to try and help as many people as possible.
Is there an issue? Send a MessageReason:
None


* In ''DanielFaust'' Daniel had an apprentice at one time, but she was killed by some sort of magical construct and he's never forgiven himself for not saving her.

to:

* In ''DanielFaust'' ''Literature/DanielFaust'' Daniel had an apprentice at one time, but she was killed by some sort of magical construct and he's never forgiven himself for not saving her.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* In ''DanielFaust'' Daniel had an apprentice at one time, but she was killed by some sort of magical construct and he's never forgiven himself for not saving her.
Is there an issue? Send a MessageReason:
None

Added DiffLines:

** In the original novelization of the first ''Star Wars'' movie, Obi-Wan Kenobi speaks of Darth Vader as "One of my brightest pupils...One of my greatest failures".
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* In ''Literature/SolarDefendersTheRoleOfAShield'', it's strongly implied that [[spoiler: Kawena wasn't careful enough with secrets, which ended up somehow getting her sister killed,]] and that's why she cares so intensely about the rules now.
Is there an issue? Send a MessageReason:
None


** The Romans lost their eagle standard in a disastrous campaign in Alaska in the 1980s. They're still sore about it.
** They made up for it with some help.

to:

** The Romans lost their eagle standard in a disastrous campaign in to Alaska in the 1980s. They're still sore about it.
**
it. They made up for it with some help.help.
** Back when Coach Hedge was still an active-duty Protector, he received a message from his mother who was being hunted and feared for her life. Hedge, [[GoodCannotComprehendEvil unable to believe anybody would hurt an innocent cloud nymph]], chose to deliver Clarisse to Camp Half-Blood before trying to help his mother. He never saw her again, and the moment has haunted him ever since.
Is there an issue? Send a MessageReason:
None


** As quoted above, ''The Yellow Face'' is a case where his theory about the cause of certain mysterious events proves to be wrong. Yes, even Sherlock Holmes makes mistakes. Within the work, it's more of a [[DownplayedTrope Downplayed]] example, as the situation resolved itself well (unlike many cases of MyGreatestFailure), and the worst harm was to Holmes' pride.

to:

** As quoted above, on the main page, ''The Yellow Face'' is a case where his theory about the cause of certain mysterious events proves to be wrong. Yes, even Sherlock Holmes makes mistakes. Within the work, it's more of a [[DownplayedTrope Downplayed]] example, as the situation resolved itself well (unlike many cases of MyGreatestFailure), and the worst harm was to Holmes' pride.
Willbyr MOD

Added: 19356

Is there an issue? Send a MessageReason:
None

Added DiffLines:

* Jake from ''Literature/{{Animorphs}}'', whenever he recalls the David incident. Also the fact that Jake couldn't save Tobias from being trapped as a hawk. Even moreso, the fact that he couldn't save [[spoiler:Rachel or Tom from dying, not to mention the order to kill seventeen thousand Yeerks. Those two failures become the entire focus of his personality for about five years]].
* ''Literature/TheBartimaeusTrilogy'': Bartimaeus feels the death of his master Ptolemy [[spoiler:in order for Bartimaeus to live]] is this, and his guilt is so bad he wears the face of Ptolemy millennia after the boy's murder.
-->'''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.
* ''Literature/{{Beachwalker}}'''s protagonist had one of these in the form of [[spoiler: her mother's death]]. She is determined to keep the past from repeating itself, whatever the cost to herself.
* In Anne [=McCaffery=]'s ''[[Literature/TowerAndTheHive Damia]]'', the title character accidentally fried the mind of [[TheirFirstTime her first lover]]. She considers it this because not only did she never consider keeping her mental guard up while with a far lower [[PowerLevel 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[[note]]Though not only did Afra actually want her, but wanted Damia to see him as himself and not just "Good Ol' family friend Afra", but she thought the whole thing was being driven by her mother, the Rowan.[[/note]] 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.
* Near the start of ''Literature/DoctorSleep'' we get a glimpse of Daniel Torrance's adult life, one spent with alcohol and drugs in order to weaken the terrible visions his shining gives him. He eventually reaches the lowest point, however, when he robs a young mother of her money. For the next couple of years, Danny can't forgive himself over this (the visions of the child and mother's deaths don't help), and it causes him to eventually stop drinking and settle in a town for good. [[spoiler:At the end of the book, 15 years later, he eventually decides to come clean and tells his friends about the deed... and is surprised to see that they don't give it much thought (being ex-drunkards like him, they had heard and done things just as bad)]].
* ''Literature/TheDresdenFiles'':
** Harry considers [[spoiler:his lover]]'s 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 HeroicBSOD shortly after it first happens. Years later, when he [[spoiler:destroys the Red Court at the cost of said lover's life]] and then learns that that act [[spoiler:cured all the other half-turned people]], he says that whatever number of people he saved, it will always be one too few.
** ''Bombshells'' reveals that Molly thinks of [[spoiler:Harry]]'s SuicideByCop this way, because she enabled it. If she'd thought through the consequences of this act, [[spoiler:the Fomor would not have such a stranglehold on Chicago]]. Notably, when [[spoiler:Harry is resurrected]], she becomes fiercely protective of him.
* ''Literature/ForeverGate'': Hoodwink never forgave himself for allowing a rich guy to brainwash his daughter into the ideal HouseWife. It led him to drinking which drove away his wife. Now he throws himself into harm way's way whenever Ari's in danger to make up for it.
* John in ''Literature/TheGrapesOfWrath'' 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.
* From the ''Literature/HarryPotter'' series:
** 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 (who similarly is wracked with self-loathing over [[spoiler: inadvertently causing a sibling’s death]]) in ''Film/FantasticBeastsTheCrimesOfGrindelwald '' that it’s his biggest regret in life.
** It could be argued that Harry's own greatest failure comes in ''Literature/HarryPotterAndTheOrderOfThePhoenix'', when his recklessness ultimately results in [[spoiler:Sirius' death]].
** 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 [[FantasticSlur Mudblood]] in anger after she comes to his defense. Later, in ''Deathly Hallows'', we find out ''why'' it's his worst memory: [[spoiler:it ruined his friendship with Lily, the only person he ever loved, and destroyed any chances of him getting together with her. And for even more Snape karma, the person she ultimately ''did'' get together with... was the reformed James Potter, [[TookALevelInKindness who had mellowed out of his bullying tendencies by then, according to Remus Lupin]]]].
** Sirius' own greatest failure: convincing James to let Peter Pettigrew become the Potters' SecretKeeper, not knowing that Peter was a Death Eater.
** Horace Slughorn regards divulging information [[spoiler: about [[SoulJar Horcruxes]] to [[BigBad the then-teenager Tom Riddle Jr., a.k.a. Lord Voldemort]]]] as this, as revealed in ''Literature/HarryPotterAndTheHalfBloodPrince''.
* ''Literature/TheHeroesOfOlympus'':
** The Romans lost their eagle standard in a disastrous campaign in Alaska in the 1980s. They're still sore about it.
** They made up for it with some help.
* Numerous characters, including the titular one from the ''Literature/HonorHarrington'' series, consider the events of Oyster Bay to be this for themselves, as Honor puts it, it was their job to stop things like that, and if they can't, what good are they to their people? To be fair, though, the people who did this had tech that was ''far'' better than even Manticore's, and it was specifically designed for stealth.
* Navidson's greatest failure in ''Literature/HouseOfLeaves'' was his failure to save [[spoiler:Delial]], a little African girl dying of starvation, and taking her picture instead. This would continue to haunt him for years.
* ''Literature/JourneyToChaos'': The death of his first three students has haunted Basilard Bladi for years and defined him as a person ever since.
* ''Literature/LookingForAlaska'''s titular character [[spoiler:blames herself for her mother's death when she was a little kid, as she was too shocked to call an ambulance]]. Later in the novel, most of the principal cast (including the narrator) gets their own greatest failure when [[spoiler:Alaska dies in a drunken car accident halfway through the novel]]. The kicker? [[spoiler:The reason she was driving in the first place was that she realized she forgot it was the day her mother died and was trying to visit her mother's grave]].
* North from ''Literature/OfFearAndFaith''. At first this is just implied to be the case with him, as he tells August he only has a single regret. Later on we see what this regret is during a flashback. [[spoiler: When North was a child, he let his three-year-old sister go outside by herself while he was supposed to be watching her. By the time their parents got home (which was about five or ten minutes later), the girl had disappeared without a trace and was assumed dead, and [[ILetGwenStacyDie North has carried guilt over that mistake ever since then]]]].
* ''Literature/ProphetsHouse'' has Sir Magnus, who lost a critical battle during a war between his patron House and its enemies. He's also TheAtoner.
* Lord Wyldon of ''Literature/ProtectorOfTheSmall'' realizes he's screwed up ''horribly'' as the training master for would-be Tortallan knights when two of them fail the Chamber of the Ordeal in one year [[spoiler:with Joren dying and Vinson being revealed as a rapist]]. One of the jobs of a training master is to make sure unworthy pages shape up or get shipped out before they get ''near'' the Ordeal, and while the squires' knight-masters didn't save them either, Wyldon blames himself for letting themselves run wild as bullies because of the "traditional" hazing. It's compounded when he knows that people will probably speak of Keladry as his greatest student when he spent most of her first two years trying to make her leave, so he resigns his post as training master and goes back to being a regular knight despite Kel trying to persuade him otherwise.
* In the ''Literature/RangersApprentice'' book ''The Lost Stories'', it's revealed that Halt's greatest failure is [[spoiler:accidentally causing Will's mother's death]]. Thankfully, nobody blames him for it.
* In the ''{{Literature/Redwall}}'' novel ''Martin the Warrior'', when [[spoiler:the title character's girlfriend is killed fighting alongside him in battle]] he blames himself and goes into self-imposed exile, setting up the events of ''Mossflower'' to which that book was a prequel.
* Jemidon from ''Secret of the Sixth Magic'' by Creator/LyndonHardy 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 [[spoiler:... which is ''insane'', because he was only ten when his folks urged him to get tested, and they're the ones who'd set ambition for one child above the life of another]].
* Twenty years before the events of ''Literature/TheSharingKnife'' books, as he faced the creatures of a powerful [[EldritchAbomination Malice]] during what became known as the Battle of Wolf Ridge; Patrol Leader Dag Wolverine lost all but three of his joint command, his left hand, his ''wife'', and [[ArsonMurderAndJaywalking the ridge in question]] in the space of an hour[[note]](the successful delaying action aspect that facilitated the death of the Malice in question was cold comfort)[[/note]]. Heroic Songs and Epic Poems have been composed since, and Patroller Dag [[TheMaidenNameDebate Redwing]] tends to slip out the back when the younger generation of Lakewalkers start in on them.
* ''Literature/SherlockHolmes'':
** Holmes often dwells on his defeat at the hands of Irene Adler in ''A Scandal In Bohemia'', although [[WorthyOpponent 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.
** As quoted above, ''The Yellow Face'' is a case where his theory about the cause of certain mysterious events proves to be wrong. Yes, even Sherlock Holmes makes mistakes. Within the work, it's more of a [[DownplayedTrope Downplayed]] example, as the situation resolved itself well (unlike many cases of MyGreatestFailure), and the worst harm was to Holmes' pride.
** Creator/AgathaChristie did a hilarious subversion of the trope, and a very obvious TakeThat against the original Sherlock Holmes example just above. Literature/HerculePoirot, the brilliant if egotist detective, retells, at [[TheWatson 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, adding, "I, who have undoubtedly the finest brain in Europe at present, can afford to be magnanimous." Hastings then immediately says "chocolate box." Poirot doesn't get the joke. At all.
* ''Literature/SisterhoodSeries'' by Creator/FernMichaels: 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 UsefulNotes/{{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.
* ''Literature/SpaceMarineBattles''' Damnos arc has two people with this problem.
** In ''Fall of Damnos'', Scipio keeps flashing back to an attack of Nurglite cultists, when he failed to stop [[spoiler:the daemon from possessing Chaplain Orad, thus holding himself responsible for deaths of two of his squadmates]]. This leads him to become a perfectionist [[UpToEleven by Space Marine standards]], and when more squadmates die to the Necrons he's having trouble accepting it truly isn't his fault this time.
** In ''Veil of Darkness'', Sicarius considers Damnos his greatest failure and is fairly confident that he'll be severely punished for losing the planet. Understandable, considering it's his first time that he ever lost as a Captain.
* ''Franchise/StarWarsLegends'':
** ''Literature/XWingSeries'':
*** 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 the poster child for HeroicBSOD and [[DefrostingIceQueen Defrosting Ice]] [[ColdSniper 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 LastSecondChance. Another Wraith, Castin Donn, was a slicer in a Rebel cell on Coruscant. When they received the broadcast of the [[Film/ReturnOfTheJedi 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 [[spoiler:Castin]] 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 [[IDidWhatIHadToDo 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 DysfunctionJunction the Wraiths are, it's not surprising these are handed out pretty liberally.
** Grand Admiral Thrawn of ''Literature/TheThrawnTrilogy'' 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 [[EarthShatteringKaboom destroy the planet]]. Pity.
** Darth Vader is both Emperor Palpatine's greatest triumph ''and'' greatest failure, as he muses upon in ''Literature/DarkLordTheRiseOfDarthVader''. He'd spent years moulding Anakin into the perfect Sith, only to have it all go to waste on Mustafar. He even considers just killing Vader, but decides against it since even in his crippled state Anakin is still obscenely powerful and there's no telling how long he'd have to wait until another strong Force user came along.
*** Should have looked on [[VideoGame/TheForceUnleashed Kashyyyk]].
* ''Literature/TheStormlightArchive'': Dalinar was passed out drunk while his brother fought and lost against an assassin. Years later, he still hasn't forgiven himself. [[spoiler:It's not until the Assassin in White comes for him that he finally forgives himself; he realizes at that time that even if he'd been there to defend Gavilar, Szeth would have killed him without breaking a sweat]].
** Also from Stormlight, Kaladin has a ''lot'' of these. Thanks to his HeroComplex, every time he loses someone, this happens, the first of which being [[spoiler:his little brother Tien, who got killed in front of Kaladin after being sent to the front lines to act as bait]]
* In ''[[Literature/EddieLaCrosse The Sword-Edged Blonde]]'', Eddie is haunted by... well, several things, but the biggest is the time he let his girlfriend (a princess, no less) be attacked and killed by a band of thugs. Most people think his failure was just not being able to protect her, but it turns out his culpability was greater than that — Eddie [[spoiler:was actually the one who escalated the confrontation to violence, out of pride and desire to impress his girlfriend]].
* ''LightNovel/TheUnexploredSummonBloodSign'': Kyousuke is driven to save people because he sees himself as bearing half the responsibility for [[CrapsackWorld the current state of the world]]. The exact reasons for this are outlined in the first book, and further elaborated on the fifth. [[spoiler:In the past, he summoned [[TopGod the White Queen]] into the world, and she fell in love with him at first sight. After interacting with her, he decided to try and use her power to help solve the problems in the world. However, others tried to gain control of the White Queen, enraging her and causing her to kill many people. The loss of so major important leaders resulted in the chaotic state of the present world. On top of that, the White Queen is now driven to make him love her again, [[{{Yandere}} at any cost]]]].
* Dimitri Belikov from ''Literature/VampireAcademy'' feels a lot of guilt over not being able to save his friend, the Zeklos lord he'd been assigned to guard, from a Strigoi attack. It's part of the reason he likes going to mass in the Academy chapel.
* Miles Vorkosigan of the ''Literature/VorkosiganSaga'' became fixated on the death of Sergeant Beatrice at Dagoola IV, [[spoiler:but moved on from this when Ekaterin, who would eventually become his wife, pointed out to him that saving her would have resulted in both their deaths]].

----

Top