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  • Downplayed in A Voice Among the Strangers: Captain Swift Dawn, one of the Royal Guards assigned to protect Jessica, loses track of her in Baltimare, and she almost gets recaptured by the Flim Flam brothers. He rescues her and ends up shielding her from a whip, leaving him with a scar across his muzzle. Jessica later learns that he refused to have it healed so that it would be a constant reminder of his near failure.
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  • Ancient Sins: During their fight, Celestia remarks that she had immense pride in Dante when he was younger, but is now ashmed at his fall from grace.
    Celestia: I remember when you were younger. You had so much potential, but you allowed darkness to wrap around your heart. You were my greatest hope, but you became my biggest regret.
  • Asha al'Wahim's ancestor from the Mass Effect/Avatar: The Last Airbender crossover Avatar of Victory was actually a pretty good general, until he made a mistake during the First Contact War that got the previous Avatar killed. As such, her entire family is considered jinxed, and she takes it upon herself to try and regain some of her family honor.
  • In the Back to the Future fanfic Back to the Future Prequel, Doc still regrets the day one of his inventions malfunctioned and crippled Holly Webb.
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  • For Naruto in Black Flames Dance in the Wind: Rise of Naruto he has two for the price of one. Defeating a powerful demon accidentally caused a horrific attack on Konoha that resulted in scores of deaths, if not hundreds. Then dealing with said attack caused him to forget about Anko who very nearly died before she was found. Worse is that Anko was only still alive due to taking multiple blood pills to replenish her lost blood, so she was conscious for the entire day she was tortured to the point of near-death. Even weeks later, Naruto is clearly tortured by his "abandonment" of Anko, at one point writing "I left her behind" on the written portion of the Chunin Exam.
  • The Bridge:
    • Godzilla Junior deeply regrets not being able to defeat Destroyah the first time they fought, as that led to his father Godzilla Senior fighting her and his death.
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    • Back when they were active soldiers, Stalwart Sentry and Fancy Pants arrived too late to prevent a dragon from killing Starlight and Moonbeam Glimmer's parents and neighbors. Though they were able to save the girls and kill the dragon, the event still haunts them.
  • In the Harry Potter story Cruciamentum Eternus, Lucius fails to stop Voldemort from killing Draco, conducts a Heel–Face Turn, and spends years trying to make up for it.
  • In The Dear Sweetie Belle Continuity: Dear Scootaloo, Rainbow Dash seems to view failing to save Applejack's parents from the Great Storm as this- at least, when she gets a note worded as such from the one responsible for said storm, she knows what he's talking about.
  • In Empath: The Luckiest Smurf, Papa Smurf sees taking his only begotten son Empath to Psychelia where he was forcibly taken from him by the Psyche Master, and then having to hear the child's "dying" screams, as this. While it would lead to his wife separating from him and having Brainy with another Smurf, it would also lead to his redemption when he became the sole parent of about a hundred orphaned young Smurfs whose parents died in The Plague that was Only Fatal to Adults.
  • Evangelion 303: This is how Asuka sees the Unit-04's crashing. Even though it was not her fault, she considers herself responsible for the failure of the mission and her best friend's death.
  • In Fate Zero Sanity, Saber has two: Her canon failure to prevent Camelot's fall and her role in Mordred's betrayal, refusing to acknowledge her as her successor due to her bitterness against Morgan le Fay. The later is only revealed after she fights an illusion of Mordred created by a trap left by Assassin.
  • In Innocence once lost Rainbow Dash blames herself for Fluttershy losing a leg during the war. She was showing off dodging enemy fire and forgot Fluttershy was flying behind her, she didn't warn Fluttershy to dodge and one of the projectiles hit her.
  • Life in Manehattan: Orange Sherbet sees her failure to be able to properly bond with Applejack during her stay in Manehattan as her biggest failure. Turns out, Applejack sees walking out on her aunt as hers.
  • Loved and Lost: Due to being banished from Equestria as hated pariahs, Princess Celestia, the Mane Five, Shining Armor, and Spike express deep regret over mistreating Twilight and inadvertently causing the Changeling invasion. This motivates them to return to Canterlot so that they can clear their names and make amends.
  • Mare of Steel: Jor-El feels this way about being unable to cure his wife's lung condition. Rainbow Dash feels the same way about being unable to save her sick adoptive father from dying.
  • In Mega Man: Defender of the Human Race, while Duo had failed to stop the Stardroids on occasion before, his greatest moment of doubt came when he watched them destroy a planet in front of his eyes.
  • In Mega Man Reawakened, Police Chief Marmalade thinks his biggest failure is voting for Wily to have a bail sum at all.
  • In Metroid: Kamen Rider Generations, just like in Gaim's post-series canon (listed below in Live-Action TV) Mitsuzane, for the rest of his life, will never live down the enormity of the sins he committed that culminated with Kouta and Mai's deaths. This portrayal of him is also coupled with Byronic traits led him to fight alongside Samus in her adventures.
  • My Hero School Adventure Is All Wrong As Expected: Hachiman regrets losing contact with Zaimokuza after entering high school and never thanking him for letting him copy his Healing Factor Quirk, especially after learning that Zaimokuza went missing and likely died without Hachiman finding out until it was too late. This is the reason why he goes out of his way to be nice to Saki Kawasaki, another student who (albeit unwittingly) provided him with a Quirk essential to his heroic lifestyle. This is also why Hachiman is so determined to do everything he can in the U.A. Sports Festival to earn himself a spot on Hiratsuka's investigative team as they look into Zaimokuza's disappearance.
  • This is the theme of the MLP:FiM fan-song Lullaby for a Princess, combined with Celestia blaming no-one but herself.
  • In one subplot of Parting Words, Applejack gets a very harsh wake-up call when she discovers how her lack of action (and good advice for that matter) with regards to the Cutie Mark Crusaders' bullying problem has essentially caused Applebloom to lose all faith in her. Learning from this mistake and fixing the damage this has done to their relationship becomes one of the focal points in the sequel The Great Alicorn Hunt.
  • In Pretender, Robin blames himself for not saving Emmeryn and feeling that he failed as a tactician for not predicting the events that led up it, even telling Chrom to let her die instead of giving up the Fire Emblem.
  • In Queen of All Oni, a Jackie Chan Adventures fanfiction, Uncle views Jade's Face–Heel Turn as this, since he noticed the scar on her chi that allowed the Queen persona to be reawakened, but didn't do anything about it since he didn't feel it was a threat.
  • Seen in Shepard's R&R. Commander Shepard chose the "Destroy" ending for Mass Effect 3, and although it saved the galaxy, it killed all the allied geth and his close friend EDI. He almost breaks down when he visits EDI's spot out of habit and remembers he caused her death, and it becomes a regular source of grief for the rest of the story.
  • In the Tamers Forever Series, this is how Rika views being unable to save Takato from dying in front of her.
    • Izzy also feels this way about being unable to save Mimi from being kidnapped.
  • Dragon Age: Inquisition's Walking in Circles: Solas, as per canon, considered his act of creating the Veil to be the biggest mistake of his life but by the time canon events start, he also considers what happened to Evelyn to be his other greatest failure. As he put it, he promised to save her but in the end, it was always her who saves him and she has to suffer for that, yet she has never once blamed or hated him and still chooses to accept him which only further his Guilt Complex.
  • Professor Oak's in Shudo cross Modern Ash: The Professor Who Observes his Charges is the fact that his son, Gary's father, grew to hate him because the Professor did not know he was conceived. While the Professor did try to reconcile, it did not go well and his son died hating him.
  • Prodigal Son: It is not until after one of the children under his supervision dies in the arena during training does Gobber retire from training, passing on that responsibility to Astrid.
  • Weight of the World: Having found a Silver-Eyed Warrior for the first time in decades, Ozpin became foolishly overconfident and reckless in his fight against Salem. Summer Rose paid for his arrogance with her life and Ozpin vowed not to make the same mistakes again.
  • This fanart makes the case that Superman's greatest failure isn't his inability to redeem Lex Luthor, save Krypton, enlarge Kandor or eradicate crime... but his total and complete failure to protect his family.
  • Apotheosis (MHA): All Might's is Villain Protagonist Izuku Midoriya's descent into evil. A Moment of Weakness and a lack of tact led to him crushing the dreams of his greatest fan and turning him into Japan's worst supervillain since All For One. The worst part is that All Might didn't even remember Izuku until he became a possible suspect for the titular Apotheosis's civilian identity. His guilt over the situation ultimately becomes a double-edged sword: while it drives him to stop Izuku before finally passing One For All onto a successor, it also prevents him from doing what is necessary to take Izuku down.
  • Gligarman in Pokémon Reset Bloodlines considers his greatest failure having not stopped the children of the criminal Heratia from killing her in front of his eyes. From that day onwards, he vowed to never let anybody die in front of him ever again, not even a criminal he's trying to stop. The next time it happened, he retired from crimefighting for a long time.
  • In Metallurgy, All-Might considers the USJ to be his greatest failure as using up most of his time dealing with petty crimes and joyriders beforehand resulted in Izuku losing a hand to Shigaraki.
  • Blood Moon: Sokka harbors a considerable degree of self-loathing for his failure to prevent the Fire Nation from capturing Katara.
  • one day at a time:
    • Damian's death is implied to be this for Jason. Jason was only present in the aftermath of Bruce's and wholly un-involved in the respective incidents that caused the deaths of Dick and Tim due to being busy with other pressing situations when they happened. Cass and him, however, were there when Damian made his Heroic Sacrifice, ending in him dying in their arms. Jason privately admits that out of all his siblings, Damian's death was always the one he regretted the most.
    • The death of Joker III. Jason considers killing the third Joker to be the biggest mistake of his life, because it led to the rise of Joker IV, who ultimately killed Bruce. He fully admits that there isn't a day that goes by where he doesn't think about what life would've been like had he never pulled that trigger. It was this event that caused Jason to become more family-oriented and, most noticeably, give up killing.
    • Dick's first great failure during his tenure as Batman were the deaths of Kate Kane and Renee Montoya during the Bat-Family's war with the Court of Owls. It's all but stated that their deaths are what drove Dick to be so obsessed with removing the Court from Gotham.
    • Dick's other, more noticeable failure is the deterioration of his relationship with his brother Tim. In one timeline, this led to Tim making a Face–Heel Turn and traveling back in time to both brainwash the world and personally murder Dick.
    • When Death of the Endless first forged the Balance, the first wielder she chose was a warrior of great renown who she instructed to kill all immortals. He did exactly that — and then started murdering innocents to keep seeing her, as he had fallen in love with her. A horrified Death promptly marked his soul when he died so he would be Deader Than Dead and chose the next wielder much more carefully.
  • Integrity's death is this for Sans in Not As Simple As A Happy Ending.
  • Here There Be Monsters: Several millennia later, the wizard Shazam still considers giving Teth-Adam powers was his biggest mistake.
    Even so, he had seemed old when he bequeathed his powers in ancient times to Teth-Adam, which was a great mistake. Then, millenia later, he gave those powers to the three youths, which was anything but a mistake.
  • In the Octonauts fanfic Junior Officers, Professor Inkling considers allowing the previous captain, Seacliff, whom was abusive to the rest of the staff, to be this.

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