My Greatest Failure / Literature

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• Jake from 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 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.
• Anxious People
  • 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. 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.
• The Bartimaeus Trilogy: Bartimaeus feels the death of his master Ptolemy 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.
• Bazil Broketail: 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.
• Beachwalker's protagonist had one of these in the form of her mother's death. She is determined to keep the past from repeating itself, whatever the cost to herself.
• In Anne McCaffery'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^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. 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.
• Former military policeman 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.
• In Daniel Faust 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.
• Near the start of Doctor Sleep 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. 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).
• The Dresden Files:
  • Harry considers 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 Heroic BSoD shortly after it first happens. Years later, when he destroys the Red Court at the cost of said lover's life and then learns that that act 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 Harry's Suicide by Cop this way, because she enabled it. If she'd thought through the consequences of this act, the Fomor would not have such a stranglehold on Chicago. Notably, when Harry is resurrected, she becomes fiercely protective of him.
• Forever Gate: Hoodwink never forgave himself for allowing a rich guy to brainwash his daughter into the ideal House Wife. 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 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.
• From the Harry Potter series:
  • It's revealed in Harry Potter and the Deathly Hallows that Dumbledore is wracked with guilt at his failure to take care of his little sister, whom both of his parents died to protect. He instead chooses to run around with Grindelwald 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 inadvertently causing a sibling’s death) in Fantastic Beasts: The Crimes of Grindelwald that it’s his biggest regret in life.
  • It could be argued that Harry's own greatest failure comes in Harry Potter and the Order of the Phoenix, when his recklessness ultimately results in 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 Mudblood in anger after she comes to his defense. Later, in Deathly Hallows, we find out why it's his worst memory: 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, 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' Secret-Keeper, not knowing that Peter was a Death Eater.
  • Horace Slughorn regards divulging information about Horcruxes to the then-teenager Tom Riddle Jr., a.k.a. Lord Voldemort as this, as revealed in Harry Potter and the Half-Blood Prince.
• The Heroes of Olympus:
  • The Romans lost their eagle standard in a disastrous campaign to Alaska in the 1980s. They're still sore about it. They made up for it with some 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, 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.
• Hive Mind (2016): 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.
• Numerous characters, including the titular one from the Honor Harrington 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 House of Leaves was his failure to save Delial, a little African girl dying of starvation, and taking her picture instead. This would continue to haunt him for years.
• The Hypnotists: 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.
• Journey to Chaos: The death of his first three students has haunted Basilard Bladi for years and defined him as a person ever since.
• Looking for Alaska's titular character 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 Alaska dies in a drunken car accident halfway through the novel. The kicker? 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 Of Fear and Faith. 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. 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 North has carried guilt over that mistake ever since then.
• Primal Warrior Draco Azul: In the short story "Reminiscence", Ekchuah reveals to Eric that his greatest failure was a battle with the Mesoamerican Feathered Serpent god K'uk'ulkan/Quetzalcoatl that ended disastrously—costing the lives of countless innocents and destroying the city of Teotihuacan in the process.
• 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.
• Lord Wyldon of Protector of the Small 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 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 Ranger's Apprentice book The Lost Stories, it's revealed that Halt's greatest failure is accidentally causing Will's mother's death. Thankfully, nobody blames him for it.
• In the Redwall novel Martin the Warrior, when 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 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 ... 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 The Sharing Knife books, as he faced the creatures of a powerful 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 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). Heroic Songs and Epic Poems have been composed since, and Patroller Dag Bluefield (ne Redwing) tends to slip out the back when the younger generation of Lakewalkers start in on them.
• Sherlock Holmes:
  • 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.
  • As quoted 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 Downplayed example, as the situation resolved itself well (unlike many cases of My Greatest Failure), and the worst harm was to Holmes' pride.
  • Agatha Christie did a 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 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.
• 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 Solar Defenders: The Role of a Shield, it's strongly implied that 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.
• Space Marine Battles' 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 the daemon from possessing Chaplain Orad, thus holding himself responsible for deaths of two of his squadmates. This leads him to become a perfectionist 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.
• Star Wars Legends:
  • 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".
  • X-Wing Series:
    • 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 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 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 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.
  • 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.
  • In the book Shatterpoint, Mace Windu muses on how his greatest failure happened in Attack of the Clones, 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.
  • Darth Vader is both Emperor Palpatine's greatest triumph and greatest failure, as he muses upon in Dark Lord—The Rise of Darth Vader. 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 Kashyyyk.
• The Stormlight Archive: Dalinar was passed out drunk while his brother fought and lost against an assassin. Years later, he still hasn't forgiven himself. 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 Hero Complex, every time he loses someone, this happens, the first of which being his little brother Tien, who got killed in front of Kaladin after being sent to the front lines to act as bait
• In 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 was actually the one who escalated the confrontation to violence, out of pride and desire to impress his girlfriend.
• The Unexplored Summon://Blood-Sign: Kyousuke is driven to save people because he sees himself as bearing half the responsibility for the current state of the world. The exact reasons for this are outlined in the first book, and further elaborated on the fifth. In the past, he summoned 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, at any cost.
• Dimitri Belikov from Vampire Academy 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 Vorkosigan Saga became fixated on the death of Sergeant Beatrice at Dagoola IV, 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.

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