Out Gambitted / Western Animation

• In the American Dad! episode "With Friends Like Steve's", Steve's mildly retarded friend Barry turns out to be a criminal mastermind kept in check only by powerful anti-psychotic "vitamins". After he goes off them and causes havoc, Steve challenges him to a game involving two cups, one of which contains his medication. The scene that follows is a parody of the one from The Princess Bride, and naturally Steve put Barry's meds in both cups. Unlike Westley, however, Steve has no immunity to the meds.
• In the Avatar: The Last Airbender episode "The Crossroads of Destiny", Long Feng and Azula are savvy enough to know they are both attempting this, but Azula's Break Them by Talking speech is just too good, and he concedes.
• In Beast Machines, Tankor/Rhinox is Out-Gambitted by Megatron when he reveals that Tankor/Rhinox can't actually hurt Megatron thanks to the Restraining Bolt Megatron hardwired into him when he first implanted Rhinox's Spark into the Tankor body.
• Big City Greens:
  • In "Harvest Dinner", Cricket and Gramma end up buying a papaya instead of the intended paprika for the family stew, so they distract Tilly and switch the groceries; however, when they get home, Bill reveals the jar is empty. Turns out, Tilly knew they would switch the groceries, so she hid the paprika in her pocket to throw them off.
  • In "Bleeped", Cricket overhears a (kid-friendly) cuss word "blort" from Gramma and becomes so amused by it that he ends up passing it to the rest of the choir children but Tilly; Bill goes to great lengths to stop the potty-mouths, to the point he ends up going "full dad" and outright frightening the kids into no longer cussing and leaving the room in silence. But it turns out Cricket only pretended to be scared because he didn't like Bill controlling his language, and plots to drop a B-bomb at the end of the concert.
• In the Season 3 finale of Carmen Sandiego, Roundabout sets up a gambit to bait Carmen into attempting to steal St. Edward's crown so that she'll get arrested and he'll be able to steal the crown easily afterwards. Unfortunately for him, Carmen and Shadow-san knew him well enough to know that he'd pull something like this and so set up their own gambit to work around his. The result: Roundabout's cover as a member of Her Majesty's secret service is blown out of the water, leading to his arrest.
• DC Animated Universe
  • Batman: The Animated Series:
    • In "You Scratch My Back", Catwoman should have known better that to try and play Nightwing, Batman's protege. He has after all been taught by the best.
    • In "Mad Love" (adapted from an issue of The Batman Adventures), Harley Quinn actually gets Batman to fall for one of her traps, but then Batman (rather expectedly) uses a Batman Gambit to exploit both her feelings for the Joker and how the Joker would react.
      Batman: She almost had me, you know. Arms and legs shackled, dizzy from the blood rushing to my brain... I had no way out other than convincing her to call you. I knew your massive ego would never allow anyone else the honor of killing me, though I have to admit she came a lot closer than you ever did... Puddin'.
  • Justice League:
    • In "Injustice for All", the Injustice League has captured Batman and begins working on different ideas to tear the league apart to defeat them. What they don't realize before it's too late is that a) Batman's manipulating them into screwing up, and b) He can escape whenever he wanted. Naturally, the Joker — the member who actually caught Batman for the team — is the only guy (except for the Ultra-Humanite) who fully expects Batman to escape, and pleads for the right to kill him immediately. Lex Luthor doesn't listen, and the team listens to Lex, which means, of course, that The Joker was the Only Sane Man in that situation. The real man who Out-Gambitted the Injustice League, though, was the Ultra-Humanite, who had already agreed to help Batman out...in return for a generous donation in his name to his favourite public broadcast station.
    • Green Arrow versus the Question in the Gail Simone-written episode "Double Date". Arrow spots Question pocketing evidence, and confiscates a locker key. Once he's gone, Question then reveals that the key was a fake-out, and the real evidence he palmed was a shipping manifest. Then we find out that Arrow knew he was being conned, and hid outside so that he could follow Question when he chased up the real lead.
    • The third season of Unlimited revolves a great deal around the conflict between supervillains Lex Luthor and Grodd. In their final confrontation in "Alive!", Luthor manipulates Grodd into using his own powers to destroy himself, resulting in this exchange:
      Luthor: Goodbye, Grodd. It could have gone the other way.
      Grodd:: It really could have, couldn't it?
      Luthor: No. But why speak ill of the dead?
• Gargoyles: David Xanatos in episode 12, "Her Brother's Keeper". No, seriously. His plan is to woo Elisa's brother to his side, first taking advantage of the fact that she can't tell him about the gargoyles (and hence why she thinks Xanatos is an evil mastermind) and then tell him his own version to make sure not even their testimony will help anymore. He even orders Fox to tell Elisa this outright, because with her brother no longer believing her, it will do her no good. Except that it does, because she brought a tape recorder. Duh. This plan is hardly Xanatos's best anyway, since it involves setting hypercompetent killers on himself with serious lethal intent and real weapons.
• In Generator Rex, all of the villains who spent the entire series scheming to obtain the Meta-Nanites, the keys to godhood, were outmaneuvered before the series even began. The Salazars — Cesar and his parents — had programmed the Meta-Nanites in such a way that only Rex could tap into their full power.
• Throughout the first season of He-Man and the Masters of the Universe (2021), Evelyn and Kronis have been plotting behind Skeletor's back to betray him and take the power he had promised but failed to deilver on for themselves. They eventually convince Skeletor to share with them the power of Havoc to counter the Masters of the Universe, who beat them soundly before because He-Man shared the Power of Grayskull with all of them. After successfully stealing Kirbinite to improve Skeletor's staff, he gives them and R'Qazz, recruited by Evelyn to help the coup, Havoc to become the Dark Masters. After Skeletor brainwashed the entire Red Legion and sent them to conqure Eternos, the Dark Masters attack Skeletor to usurp the throne for themselves. Skeletor then reveals he never needed the Kirbinite to empower them with Havoc, but to control them with Havoc, proving he always suspected their treachery and placed them completely at his mercy.
• Looney Tunes
  • Elmer Fudd and Yosemite Sam are "masters" of this trope.
  • As is "super genius" Wile E. Coyote, at least in those shorts where he's pitted against arch Karmic Trickster Bugs Bunny. (In the Road Runner shorts, he's not really outwitted so much as victimized by fate, gravity, poorly designed ACME products, and his own ineptitude.)
  • Daffy Duck is a victim of this due to Hoist by His Own Petard. ("Wabbit season!" "Duck season." "Wabbit season!" "Duck season." "Wabbit season!" "Wabbit season." "Duck season! Fire!"
  • The theatrical compilation film 1001 Rabbit Tales starts with Bugs and Daffy as door-to-door booksellers. After they get out of the opening meeting with their boss at the publishing company, they take the elevator down. Daffy switches territories with the utterly apathetic Bugs about six times.
• In My Little Pony: Friendship Is Magic:
  • Discord has seemingly won, having broken Twilight and brainwashed her friends so they can't use the Elements of Harmony against him. What Princess Celestia does next is send back all of Twilight's friendship reports, and the memories sparked by reading those old letters convinces Twilight to fight for her friends and the bonds they share. That way, Celestia outwitted a Reality Warper spirit of chaos by mailing a bunch of letters.
  • In "Keep Calm and Flutter On", Discord tries to ensure his safety by driving a wedge between the Mane 6 and getting Fluttershy to promise never to use the Element of Kindness against him. However, Fluttershy knew this was happening and managed to reform him by threatening to withdraw the friendship she had been building with Discord throughout the episode, which made Discord realize that her friendship did matter to him.
  • In "The Cutie Map Part 2", Starlight Glimmer is hit with this when the Mane Six use a Fake Defector gambit to turn her attempt to brainwash them against her and ultimately set up an Engineered Public Confession.
    • And again in "Viva Las Pegasus", involving an Enemy Mine alliance between Applejack and the Flim Flam Brothers, who make Gladmane think he's thwarted their Engineered Public Confession gambit and gloats — Oh sulat, my gloating's just been broadcast on the PA!
• In one Rick and Morty episode, Rick is kidnapped and put in a simulation of his life by alien scammers who are, once again, trying to steal his formula for concentrated dark matter (a powerful spaceship fuel). Rick knows he's in a simulation, but this time the aliens are prepared for this, and allow Rick to think that he's escaped the simulation and is returning home, and then enter the code to his safe filled with scientific secrets... before revealing that he was still in the simulation, they always had his formula, but now they have the code to his safe too. Rick tries countering this by escaping and attempting to fly home to change the safe code, but while being chased in the flight back to earth he needs to mix up some more of his special high-power fuel to escape. But as soon as he instructs Morty on which ingredients to mix, it's revealed that — once again — he's still in the simulation, and now the aliens have his formula. The aliens, flush with pride and having finally gotten what they wanted, let Rick leave. As Rick flies back to Earth, the aliens throw a party for their success and prepare the first batch of concentrated dark matter, only for the formula to result in a volatile compound that instantly destroys their entire ship.
• She-Ra and the Princesses of Power: Twice in Season 4, a scheme involving Double Trouble leads to this happening to someone. In "Mer-Mysteries", Double Trouble gets caught because Adora and Glimmer set a trap in the dining room, baited it with a lie about a backup communications unit that DT would have to destroy, and staged an argument to provide a "distraction" that DT would be able to exploit; even though that specific job of DT's was a success because it distracted the princesses from the conquest of Salineas, being captured takes them out of play until they switch sides out of self-interest. After switching sides, they blow open Catra's manipulation of Hordak by tipping him off about the real reason Entrapta disappeared; Hordak's resultant rampage sets a decent chunk of the Fright Zone on fire and is only stopped when Catra destroys his Arm Cannon and crushes him under a pile of metal, which combines with the Hordes' forces being stretched thin and Catra being rendered virtually catatonic by DT's Breaking Speech to leave the Fright Zone virtually undefended when Glimmer and Scorpia infiltrate.
• South Park: Scott Tenorman. He thought he was getting around Cartman's Batman Gambit, thanks to some sabotage by Stan and Kyle. Instead, Cartman caused all three of them to run straight into another one that was far, far worse and ended with Scott crying the delicious tears of unfathomable sadness.
• Star Wars: The Clone Wars had Obi-Wan and Anakin negotiate for a captured Count Dooku. The negotiations concluded, they celebrate by having a party. Our heroes are wise to the fact their drinks are spiked, and use the Force to switch theirs with some nearby partiers. Not to be outdone, Hondo poisons all the air in the room.
• Star Wars Rebels: In Grand Finale "Family Reunion -- and Farewell", an outgambit gets defeated by another outgambit. The Rebels take the main dome of the Imperial complex and make preparations to launch it into space with all hands on board, essentially wiping out the entire occupying force of Lothal in one swoop. Thrawn arrives and puts his own Star Destroyer right above the dome to prevent the launch, while secretly sending his own team to disable the city shields, and then fires upon the city until Ezra agrees to surrender himself. However, Ezra realized that Thrawn might arrive and made a contingency plan: summon a gigantic pod of purrgil that he'd previously befriended and use the Force to direct them to disable the Star Destroyers' hyperdrives, then use the purrgil's own natural abilities to hyperspace the entire fleet to somewhere they can't return from.
• In Teen Titans (2003), Robin creates the identity of Red X so he can finally meet with Slade. Slade figures this out and not only does Robin only meet with a Sladebot, but this causes tension between him and his friends.
  • Robin manages to get one back on Slade a few episodes later. Slade injects the other Titans with deadly nanites and forces Robin to be his apprentice or else he'll activate them. Robin ultimately wins by injecting himself with the nanites, thus forcing Slade to release them since he wants Robin alive.
• In Young Justice (2010), this happens to the Light on a few occasions. Near the end of the first season, they try to use blackmail to get Artemis, Superboy and Ms. Martian to join them, but they defuse the blackmail by telling the other team members their secrets. Then they manage to create a cure and vaccine to the mind-controlling Starro-Tech, and catch the Light by surprise, allowing them to free the JL from the Light's control. Then, in Season 2, not only does Aqualad get the Light and Reach to admit their actions, he also revealed how they had double-crossed each other at multiple points, utterly shattering their alliance. Then in the third, for Vandal Savage, a 50,000-year-old immortal himself says that no one has ever upset his plans like that in his entire life. Then the Team shows up, and not only did the Light fall for Aqualad and Artemis's fake deaths, the Team managed to infiltrate the assassins and capture nearly half the Light.

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