History OutGambitted / FanWorks

** During the ''Forever Red'' arc of the sequel ''Ghosts of the Past'', Russian President [[NoCelebritiesWereHarmed Volodya]] attempts to shut down the [[SovietSuperScience Red Room]] by meeting with [[GeneralRipper General Lukin]] while backed with a small army, all of whom are equipped psychic dampeners in case Lukin tries to have one of his telepathic minions take control of them. Unfortunately, the minion Lukin brought with him is [[LivingWeapon the Red Son]], who telekinetically destroys all of the dampeners and the soldiers weapons before killing them all, allowing Lukin to kill Volodya and seize control of Russia.

** Ozai knows about the planned invasion on the Day of Black Sun. But Long Feng learns this and warns the invaders, causing them to change targets; Ozai spends the eclipse hiding inside his volcanic bunker in Caldera City while the raiders launch a massive jailbreak, freeing every prisoner in the war camps across the Fire Nation before destroying the facilities. The fact that two of these prisons were situated on the Fire Nations' largest Naval Shipyard and primary Weapons Factory was just the icing on the cake.

* ''Fanfic/DodgingPrisonAndStealingWitches'': Dumbledore frames Harry for attempted murder of his twin John and convinces the boys' parents to let him defend Harry at trial, intending to lock Harry up in Azkaban until he has to face Voldemort. Unfortunately, not only does Harry refuse to sign a confession, but the prosecution informs him they plan to push for execution. Come the trial, Dumbledore learns that not only is the prosecution pushing for exoneration, but a good deal of evidence he thought was inadmissible is presented. Due to the prosecution insisting the defendant is innocent and the defense declaring him guilty, Amelia forces the two to switch sides.

* ''Webcomic/FeralnetteAU'': During the ''Birds of a Feather'' arc, Lila angles to get Marinette expelled again, this time for good. However, once she manages to get her target in the principal's office, she's shocked to learn that ''Chloe'' has outplayed her; having anticipated that Lila might [[NeverRecycleYourSchemes pull the same stunt]], she informed the principal that Marinette was "tutoring" her, warning him that if he expelled the other girl again, she'd [[ScrewTheRulesIHaveConnections get her father involved]]. Marinette then negotiates a punishment that [[BriarPatching works in her favor]], and alerts Ms. Mendeleiev that Lila was "being weird" about [[PoliticallyIncorrectVillain a friend's gender identity]], getting the BitchInSheepsClothing into more trouble than her target was.

* ''Fanfic/BadForBusiness'': Roman poses as a FakeDefector in an attempt to find the White Fang's headquarters, only for a ''real'' defector to reveal his plan to Cinder. Cinder then uses Roman as bait for a trap, intending to catch his allies... but rather than contacting his ''allies'', Roman calls in an anonymous trip to Ozpin about the base's location, who sends [[SummonBiggerFish Glynda and Team CFVY]] to raid the place, providing him with the perfect distraction.

* In ''Fanfic/RiskItAll'', [[spoiler:Ren's grandparents conspired to kill his father to prevent him from ever challenging Ren's uncle for the position of patriarch of their clan. They didn't count on Ren's father going as far to torch their ancestral home and plant explosives to create a diversion and escape]].

** During the Siege of the North, Alex and the Gaang catch Zuko by setting a trap in the Spirit Oasis. The following night, Zhao arrives with five times the amount of soldiers they'd expected him to bring... along with Iroh. Alec immediately informs Iroh that they have Zuko hostage, but will let both of them go free if Iroh helps them defeat Zhao. Iroh instantly agrees, proceeding to hold off three-quarters of Zhao's forces by himself.
** Ozai knows about the planned invasion on the Day of Black Sun. But Long Feng learns this and warns the invaders, causing them to change targets; Ozai spends the eclipse hiding inside his volcanic bunker while the raiders launch a massive jailbreak, freeing every prisoner in the war camps across the Fire Nation.

* ''Fanfic/BadForBusiness'': Roman poses as a FakeDefector in an attempt to find the White Fang's headquarters, only for a ''real'' defector to reveal his plan to Cinder. Cinder then uses Roman as bait for a trap, intending to catch his allies... but rather than contacting his ''allies'', Roman calls in an anonymous trip to Ozpin about the base's location, who sends [[SummonBiggerFish Glynda and Team CFVY]] to raid the place, providing him with the perfect distractioin.

* In ''Fanfic/{{Mergers}}'' Brock chooses to be merged with Steelix for pragmatic reasons given its strength and difficult capture rate, but unfortunately the Rockets were prepared and catch him in a Master Ball.

* ''Fanfic/{{Antipodes}}'': Rubidium kills the Attenuator for Stalliongrad, banking that Jigsaw will give himself up to save the city before Tantalus realizes Stalliongrad is defenseless. However, Tantalus sent Jigsaw and Tiptoe to him in the first place, banking that they would lower the shield somehow, and was ready to attack at a moment's notice.
* ''Fanfic/RosarioVampireBrightestDarkness Act IV'': After learning that Hokuto is apparently planning a full-on attack on Yokai Academy to capture Moka in the future, Tsukune and co. take time to prepare. However, they fail to consider the fact that Luna and Falla, two {{Time Master}}s, weren't present during the attack in ''[[AlternateTimeline that]]'' [[AlternateTimeline timeline]], and are caught unprepared when Hokuto ''does'' factor in Luna and Falla's presence and instead has [[CoDragons Jovian and Jacqueline]] kidnap Tsukune's mother and cousin and hold them hostage at opposite sides of Tsukune's hometown in order to DivideAndConquer the group while a BrainwashedAndCrazy Felucia forces Moka to go with her to Hokuto without a fight.
* ''Fanfic/RealityChecksNyxverse'': ''Alicornundrum'' has [[spoiler: Prince Blueblood's father, Duke Blueblood. He tries to con Twilight into a marriage contract with his son. Unfortunately, he never considered: 1) Twilight is ''not'' going to take it lightly, 2) [[MamaBear Celestia's]] reaction if she finds out (which she does indeed). 3)Threatening or trying to boss around Twilight or [[GodEmperor Celestia]] carries ''bad'' consequences]].
* ''Fanfic/TheEquestrianWindMage'': Once Vaati discovers Queen Chrysalis's ruse during the Canterlot Wedding episode, he secretly transports all his monsters to Canterlot (while having Celestia secretly evacuate the city's civilians), and then ''allows'' the Changelings to attack, which triggers an utter massacre once his monsters reveal themselves.

* ''Fanfic/TheUltimateEvil'': During the climax of the Demon Portals arc, the J-Team and Shendu [[EnemyMine team up]] to open the last portal so that Jade can escape from the Netherworld, in exchange for the Chans' friend (and object of Shendu's [[VillainousCrush obsession]]) Valerie Payne surrendering herself to him. However, Uncle realizes that Shendu is probably planning to double-cross them all when the time comes, so he already has a spell in place to banish him before he has a chance to. [[spoiler:Ironically, Shendu's [[EtTuBrute subsequent interactions with Valerie]] when he [[DemonicPossession possesses her]] imply he genuinely wasn't going to leave any strings attached when upholding his end of the bargain.]]

* ''Fanfic/SecretsOfTheEmeralds'': Knuckles, of all people, pulls one on ''Robotnik''. When he tries to rescue Sonic from Robotnik's fortress, Sonic asks him to tell him what the real secrets of the Chaos Emeralds are. Knuckles explains that each emerald has a different power, depending on the color, and gives the light blue one as an example, telling Sonic that it's a teleporter. When Knuckles is captured and brought in front of Robotnik, the doctor mockingly tells him that the conversation was recorded and uses that Emerald on Knuckles to transport him into a cell. Unfortunately for him, Knuckles was well aware (or at least, strongly suspected) that Robotnik might be listening. Turns out that the light blue Emerald that Robotnik uses on the badly injured Knuckles has the power of healing, ''not'' teleportation.
* In ''Fanfic/RiskItAll'', [[spoiler:Ren's grandparents conspired to kill his father to prevent him from ever challenging Ren's uncle for the position of patriarch of their clan. They didn't count on Ren's father going as far to torch their ancestral home and plant explosives to create a diversion and escape.]]

** [[spoiler: Bloodraven foresees Euron's LongGame (gain Stannis' trust until he can become Hand, become regent for Stannis' children after eventually killing him, marry one of his daughters to become king) and [[TheChessmaster arranges events]] to have him killed during the above-mentioned battle at Fair Isle.]]
* ''Fanfic/SecondBiteOfTheCherry'': Jin Guangshan offers one of his bastard daughters as a bride to Lan Wangji, hoping to ally with another powerful Great Sect and make it seem the very honourable Gusu Lan are alright with his immoral conduct. Unfortunately for him, the Lan elders already have trained a bride for Lan Wangji ''precisely'' to avoid this kind of political trap.
* ''Fanfic/PokemonHarmonyAndChaos'': This happens to Team Shadow when they first try to invade the Crystal Empire. [[spoiler:[[BigBad Sombra]] is able to enter the Crystal Empire without issue [[TheMole due to being on good terms with everyone]], and secretly installs a virus in Androrg that messes with its security list in its systems, allowing Chrysalis and the grunts to invade while also turning Androrg and all the Guardroids against everyone in the Crystal Empire. Team Shadow attempts to obtain the Heart Fragment of the Crystal Heart and the Shadow Spear, contained in two cases, with Sombra subtly assisting them by taking the cases and planning to hand them off to one of the grunts and make it look like he was robbed, and Chrysalis at one point [[HostageForMacGuffin pretending to threaten his life to force everyone to hand over the cases]]. In the end though, although Chrysalis manages to snatch both cases and escape, she finds out too late that Shining Armor and Cadance already thought ahead and hid both of the artifacts somewhere else. The cases were just empty decoys, and the whole battle was just buying Cadance time to remove the virus and get Androrg and the Guardroids back on their side so Team Shadow could not immediately attack again after realizing they were tricked, or try the same trick in the future. The only silver lining for Team Shadow is that Sombra managed to keep his cover, with nobody realizing he is the leader of Team Shadow.]]

* In ''Fanfic/FateZeroSanity'', Gilgamesh believes that he is the Fourth Grail War's resident MagnificentBastard as in [[LightNovel/FateZero canon]]. He is gravely mistaken and ultimately taken advantage of by Assassin![[spoiler:[[Manga/{{Naruto}} Obito Uchiha]]]], the War's true MagnificentBastard, ending in [[spoiler:Gil's death via Saber and Berserker when Obito steals Tokiomi's Command Seals and orders Gilgamesh to attack the latter two]].