Failure Gambit

"See? Being defeated by the Mazoku was precisely the cathartic jolt he needed to resolve his inner turmoil and pay off his guilt."

— Itsuki, YuYu Hakusho

Let's face it. Sometimes a villain's (and occasionally even a hero's) great big, all-encompassing master plan can be... a little convoluted. It might not make complete sense even after it's finally been thoroughly explained at the end of the day. But it's a special kind of deviant who is able to conjure a plan so incredibly obtuse that it hinges on their own defeat, and will inevitably fail should they happen to win. Somehow, some way, someone has managed to twist the plot completely on its ass to the point that the only way for them to win is to lose, and the only way to lose is to win. That Magnificent Bastard.

This presents an especially dangerous situation to their opponent, who is usually out of the loop on this grand master plan. After all, what can the unwitting hero do when beating the bad guy means ending the world, and losing will actually save it? Sometimes a character seeks to become a political martyr in order to inspire others to take action after their crippling defeat (Inspirational Martyr), others might be tied to some ultimate power that will unleash itself upon their death (My Death Is Just the Beginning). Still, others don't seem to make any sense until after the plan has played out successfully— surprise! Turns out that ass-kicking you just gave them was all they needed to transcend the mortal coil and become a god.

The bottom line is, this is what you get when a character deliberately sets out to fail for some intended positive outcome. The failure of such a plan — that is, accidentally succeeding, or failing to fail — results in a Springtime for Hitler. Note that a scheme that has a beneficial outcome for the schemer whether he/she succeeds or fails is not an example of this trope, but of a Xanatos Gambit. In order to qualify here, the plan must be thought of well in advance, and it must completely hinge on failure. Without the threat of the plan failing if one fails to fail, it fails to qualify.

The plan usually relies to some extent on a Batman Gambit, and often one's only hope of overcoming the plan is to Sheathe Your Sword... or occasionally Take a Third Option.

The inverse of this trope is a Pyrrhic Victory — a successful endeavor that ultimately results in an undesirable outcome, which is usually what the opposing party of a Failure Gambit planner experiences. Gone Horribly Right also arguably qualifies. A Failure Gambit often overlaps with I Let You Win. A character who plans on taking harm in such a plan overlaps with Deliberate Injury Gambit. A character seeking to end his or her own life with such a plan also falls under Suicide by Cop, as well as Thanatos Gambit.

Springtime for Hitler is a Sub-Trope — specifically, a failed Failure Gambit. See also Throwing the Fight for a sports version. Compare Death Is the Only Option.

As this is an Ending Trope, unmarked spoilers abound. Beware.

Examples:

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Anime and Manga

Food Wars!: The final arc shows Joichiro Saiba losing a Cooking Duel against his disciple/adopted son Asahi in what looked like a Curb-Stomp Battle. Later on, Joichiro's biological son Soma implies that Asahi only won because Joichiro was deliberately holding back, and it's all but stated that Joichiro set this up purposefully to make his two sons face each other.
Heavy Object. The Northern Restricted Zone is home to several prototype superweapons which all fail soon after deployment due to flaws in their design. This is an intentional gambit by the four officers overseeing the Zone. The home countries want proof that no other weapon can rival Objects on the battlefield, so the officers develop superweapons whose failure act as that proof. This ensures the home nations continue to funnel money into the Zone, which the officers can skim off of while building yet more flawed machines.
Liar Game. Players of the Liar Game Tournament are forced to participate and pay an enormous debt if/when they lose. At first, the goal appears to be to win each round and move on to the next round with large amounts of money as winnings. However, the real way to win the game is to deliberately lose and drop out of the game while hauling in a profit. But because it's a zero-sum game (one person winning means another person loses), Nao and Akiyama's goal is to win and move on to the next round while shouldering an enormous debt, using all of their winnings to zero out the debt of their teammates and/or opponents so that they can all safely drop out of the game.
- The final game turns into this: with both surviving teams tied at 1 hit point each, neither team can attack the other without dropping their hit points to 0. Under the game rules, nobody can win the prize money anymore... so Akiyama suggests that they use a loophole and perform a filibuster. Since the Liar Game office officially stated that any lie told by the sponsors means paying everyone in the game a huge sum of money, and they said that the game would not kill anyone and would have a winning team, that means they could hold out with food supplies and force the sponsors into paying the lie penalty. So basically, they created a situation where failure is the only option, but that failure is now directed toward the game sponsors.
Naruto:
- Itachi Uchiha had planned for his brother Sasuke to kill him in order to make Sasuke a hero of Konoha village in a Zero-Approval Gambit/Thanatos Gambit. Unfortunately for him, further manipulation by Tobi just manages to make Sasuke hate Konoha.
- Tobi's plan in Naruto the Movie: Road to Ninja. It banked on Naruto winning in a specific way so the Kyuubi's seal would be weakened in the same way it was for Kushina after his birth. Though Tobi even remarked that Naruto performed a lot more admirably than expected.
- Also Tobi's plan in canon. He pulls Kakashi and himself into Kamui, isolating the two of them from the rest of the fighting and enter with him into battle in order to remove Madara's seal as it prevented him from becoming the Ten Tails Jinchuuriki. So he allowed Kakashi hitting him in the heart, to remove Madara's seal and become Jinchuuriki.
Paranoia Agent. Though it's never fully explained why, the only way that Lil' Slugger/Shonen Bat is finally thwarted and life restored to some semblance of normalcy is for the giant wave of paranoia that Slugger has become to devour EVERYTHING, resulting in the utter annihilation of the city and a strange inner-world revelation by Tsukiko that results in Slugger's ultimate erasal. The ending is so incredibly vague that it's impossible to determine if Slugger had planned this outcome, but given that he and Maromi are functionally the same entity in Tsukiko's mind, it could be argued that they both wanted only for Tsukiko to find inner peace.
Slayers. While his defeat in the first season of the Slayers anime was not necessarily intentional or foreseen, in Slayers Evolution-R, the villain Rezo reveals that he intentionally set up a situation in which he would be defeated by Lina and the evil lord Shabranigdo sealed inside of him would be released. In true Heroic Sacrifice style, he realized that this was the only way for the mighty demon lord to be erased from existence once and for all, making Rezo less of a villain at the end of the day.
YuYu Hakusho's villains have a habit of relying on these, usually in conjunction with Suicide by Cop. Toguro, as Genkai's former teammate, seeks his own death at the hands of Yusuke, her student, for reasons only speculated in the series — perhaps as a form of atonement, or to prove to himself that the decision he made to abandon his humanity was a mistake. The second Big Bad, Sensui, sought to go to the Demon World simply so that he could intentionally die there after seeing the world inhabited by the creatures he felt remorse for over formerly hunting and killing. The fact that Yusuke, a human-demon hybrid, killed him, was a bonus.

Fan Works

Downplayed in Aftermath. After spending months grieving for her deceased friends, what eventually gets Rapunzel out of her depression is some good ol' Slapstick Comedy. After that, Varian got the idea to deliberately let some of his inventions blow up in his face just to make Rapunzel smile and laugh.
A Champion in Earth-Bet: Skylance attempts this when she offers to surrender peacefully to the Guild. She's banking on the notion that this will make her into a martyr for her ultranationalist supporters. A major wrench gets thrown into her plans when Fuji-sama arrives, berating her for her apparent cowardice and encouraging her to team up with him to fight off the Guild.
Children of the Grimmlands has Cinder sending the titular children to their first actual mission outside the Grimmlands knowing that it won't go well. She does this in order to teach them that real missions are nothing like what they're accustomed to when training at home in a safe, controlled environment.
Erika the Radical: Karen stages an apparent coup, ostensibly with the intent of driving the Nishizumi school out of existence. In reality, however, Operation Valkyrie was meant to force Erika to embrace her own style of sensha-do, spurring her to adapt and employ unorthodox tactics in order to defeat Karen and her followers.
Exodus (Worm): Prophet intentionally engineers matters so that the heroes will lose their initial conflicts with Godfrey, as part of a larger scenario that would result in the villain ultimately losing while Prophet and their friends would be given protection from those who'd want to exploit them to their own ends.
It's For a Good Cause, I Swear! has Team Seven travel back in time in hopes of doing things better the second time round. In order to ensure they don't have to waste too much time doing D-rank missions, they deliberately keep screwing them up until they're outright banned from taking them anymore, "forcing" them to move up to C-ranks. They wind up holding the record for the most consecutively failed D-ranks.
In Mega Man: Defender of the Human Race, Terra deliberately lost to Duo to distract him from Sunstar and Luna destroying a planet... and enacting a contingency plan, allowing the surviving Stardroids to repopulate their race.
Persona 5: Hoshi to Bokura to: Kamoshida has Yamauchi reestablish the school's Track Team with the intent of sabotaging it, making his Volleyball Team look even better by comparison.
Platinum Pirate: After Crocodile realizes that Lucas and his team are too powerful to defeat and that Smoker, whom Lucas is in contact with, knows his plans and is in the process of exposing him, Crocodile discards Operation Utopia, reorganizing all of his resources for Operation Prometheus, which boils down to finding the Poneglyph, stealing it, and then escaping the country before anyone is the wiser. And the most important factor of this plan? Crocodile losing, lulling the good guys into a false sense of security. While everyone else thinks that the war is over, Mr. 3 infiltrated Smoker's Marines to pull a mass jailbreak and Robin is coercing King Cobra into leading her to the Poneglyph on pain of blowing up the city, with Mr. 2 posing as King Cobra and the Mr. 4 team building a tunnel to steal the Poneglyph away underground. If it weren't for Mr. 2 having an attack of conscience and revealing the plan, Alubarna would have been destroyed and Crocodile would have gotten away with nobody the wiser.
Rise of the Last Villain: Izuku's plan with the League of Villains. His goal was never to defeat the heroes, as he knew that wouldn't be possible. His goal was instead to defeat the heroes who weren't worthy of the name, leaving only the true heroes (who would inevitably defeat the League) to fix the system in the wake of the League's "war". This plan succeeds in its entirety.
The Umbrella of Almightiness: In order to put himself Beneath Suspicion, Hagrid intentionally sets himself up to be framed by Tom Riddle and expelled.

Films — Animated

In Cars 2, oil baron Sir Miles Axelrod's attempted ploy. He staged an incident where he was lost in the wilderness and converted into an electric car when he emerged alive and created an oil-free fuel named Allinol to take regular fuel's place and featured it as the only fuel type in his own World Grand Prix. During said Grand Prix, cars that used Allinol as fuel and were targeted with a special microwave would burst into flames and exit the competition, creating bad publicity that would "force" Axelrod back into the oil business and kill the fledgling oil substitute industry, allowing big oil to stay on top. But then Mater happened.

Films — Live-Action

In Law Abiding Citizen, a regular Disproportionate Retribution training film, Clyde Shelton confesses to a murder because he wants to be imprisoned, as that becomes key in his plan, while ironically giving him more freedom than he would have had otherwise.
Marvel Cinematic Universe:
- In Avengers: Age of Ultron, Scarlet Witch deliberately allows Tony to take possession of Loki's scepter when the Avengers broke into Strucker's fort knowing that Tony couldn't resist the temptation of using it. She just didn't predict Ultron, but she was right on it.
- In Avengers: Infinity War, having seen the only version of the future out of 14 million where the heroes win, Doctor Strange trades Thanos the Time Stone in exchange for Thanos sparing Tony Stark and thus enables him to wipe out half the universe, including Doctor Strange himself, but not Tony. Five years later, Tony's brilliant mind enables the other Avengers to travel through time and undo Thanos' decimation. Bonus points for Tony being able to kill Thanos and his army in the same way he killed everyone else.
The Producers: As the Trope Namer for Springtime for Hitler, this film naturally has a plot built on a Failure Gambit (a financial fraud) — which goes spectacularly right, in the wrong way. Specifically, they went to gullible rich old ladies and persuaded them to buy shares in the production. Because the percentages they sold totaled much more than 100%, it would be necessary for the production to fail in order for the scheme to work and for them to keep the money. When the show turned out a hit, they were unable to pay the percentages that by definition far exceeded the box office take. The better the production did, the more in debt they would be. It doesn't end well for them.
Shot Caller: Jacob deliberately uses Shotgun's cell phone to tip off the authorities about the illegal weapons deal taking place in the Salton Sea. He gets arrested and refuses any deal they throw at him to inform on his bosses, going back to prison specifically to confront the Aryan Brotherhood leader and replace him.

Literature

Isaac Asimov's "The Bicentennial Man": In his quest to be legally recognized as a human being, Andrew Martin (an android with large financial resources) engages in this. He tries to void legal obligations to people with artificial organs, on the grounds that they're no longer human. Naturally, this is challenged in court, and his lawyers contrive to take it to the highest possible court before losing. As a result, they have a clear ruling precedent that humans are recognized as human, no matter how much of their body is synthetic.
In A Certain Magical Index, the "Level 6 Shift" experiment had Accelerator fighting clones of Mikoto in an attempt to have him exceed the limits of esper powers and become a god. When Mikoto and Touma get it shut down, the 10,000 surviving clones are sent to facilities around the world for treatments that will give them a normal human lifespan. Then it turns out that "sending clones of Mikoto around the world" was Aleister's true plan all along, since he can use their Hive Mind to blanket the world in linked AIM Fields; the Level 6 Shift project was just a smokescreen that let him do it without arousing suspicion. It's eventually revealed Aleister deliberately designs all of his plans this way because he's been "cursed to eternal failure", and thus the only way his true plans can succeed is by building on the failures of lesser plans.
In Dune, Paul Atreides lampshades this in his own mind as one of the possible outcomes just before his final duel with Feyd-Rautha. His thought is "If I die, they'll say I sacrificed myself so that my spirit might lead them", but this is a case of being able to foresee how his actions will be perceived rather than his actual intent.
In Good Omens, Newton — who suffers from a supernatural inability to work with electronics — is able to shut down a military computer network by simply trying to fix it.
During the events of The Hobbit, Sauron gets himself ejected from Dol Guldur by the White Council, but this seeming defeat was actually a long-prepared move back to his real stronghold in Mordor.
In Rogue, Kiara deliberately flunks her tests so she'll be able to stay at home and attend summer school with Chad instead of spending the summer with her mami in Montreal.
In Shards of Honor, the whole plan of the Barrayaran Emperor Ezar hinges on his losing the war he began. He had to kill his sadistic son to avoid another mad emperor, but also wanted 1) to give him at least an honorable death in battle, and 2) to cripple the war party for the next decade with such a resounding defeat, to ensure peace. So he began a war after secretly learning his enemy had a crushing technological superiority that would ensure the defeat of his army, led by his son.
In the Warrior Cats book Shadow, after realizing his birth Clan needs him, Nightheart intentionally fails his final task to join ShadowClan so that he's free to re-join ThunderClan and it'll be less embarrassing for Sunbeam than him just up and leaving her.

Live-Action TV

Farscape: Pirates board Moya while searching for a former colleague, who has gone with D'Argo to rescue Aeryn and Crichton from the pirates' net. The pirates avoid deadly force because Moya is pregnant and they fear her retribution, so they set up camp and wait. Rygel accepts a challenge from the lead pirate to play a strategy game that involves lots of betting and bluffing, and ultimately he wagers the location of their quarry. Despite Zhaan's psychic attempts to help Rygel win, he loses the game and forfeits the intel, and the pirates go on their way. Afterwards, Rygel laments to Zhaan how hard it was to lose convincingly because his opponent was an abominable player; he knew the pirates would never leave empty-handed and had planned all along to trick them into leaving with fake coordinates.
The infamous Eurovision episode of Father Ted was a send-up of this trope as applied to Ireland's long winning streak, which became too much of a good thing. Suffice to say the gambit worked.
My Name Is Earl. In an early episode, Earl's El Camino is impounded with the bulk of his lottery winnings in the glove compartment. To get it back, he tries to help Randy get back into high school football and then bet on the game. Randy plays, but his team unfortunately loses. Earl then wonders what he's going to do until Randy drives up in the El Camino. It turns out that he had made a bet as well...against his own team.
The Punisher (2017): Frank Castle drops into Carson Wolf's large house through the chimney, accosts Wolf when he comes home from work, and ties him to a chair. He then proceeds to torture Wolf for a little bit for information on David Lieberman, but Wolf says he's been to Guantanamo Bay and knows torture is ineffective, and even points out that Frank is answering his own questions. Of course, Frank has left Wolf's restraints just loose enough that he is able to free himself and disarm Frank of his gun. He unmasks Frank, and then gloats the information Frank wanted to hear about Lieberman. Wolf then prepares to execute Frank... but Frank has already emptied the gun.
In the Korean show Taxi Driver, Park Jin Eon goes undercover inside a voice phishing operation and intentionally does a poor job. He prearranges to make all his calls to Ahn Go Eun so as not to victimize anyone, but also so that he goes through too many burner phones without generating enough of a profit to justify it. The scammers need new phones fast, so they don't question the timing of their "chance" meeting the day before with a mysterious man (Kim Do Ge) who can hook them up.
This is the core idea of Ted Lasso: the titular coach is hired to manage an English association football team, despite being an American football coach (and a minor-league one, at that) who doesn't know the rules of the game and has almost no familiarity with association football culture. As it turns out, the current owner of the team is the ex-wife of its former manager, and she wants to run the team into the ground as vengeance for his infidelity and emotional abuse. This is a rather zigzagged case of Springtime for Hitler, as, while Ted is a great coach who genuinely gives the effort his all, he's still well out of his area of expertise.

Music

This is often a hidden goal for less affluent countries in the Eurovision Song Contest. The country whose entry wins the contest gets to host it the following year, an extremely expensive undertaking. As a result, many countries deliberately send bland acts that they know won't win, but they can say they participated. This can also happen with countries that did win the previous year and don't want to host it a second time in a row.

Radio

In The Men from the Ministry episode Conference Trick, Lord Stilton and Sir Gregory send the incompetent staff of General Assistance Department to Paris' international conference to buy pieces of Venus in hopes that they'll screw up and end up with nothing (They can't afford to have landowning-rights on Venus you see). In this case it fails since the trio are so incompetent that they end up getting the whole planet, not to mention every other nation had the same idea.

Tabletop Games

Generally, the class of games known as "misère games", where the rules of a game are altered so that it's "played to lose", i.e. the game condition that loses the normal game will win you the misère game. Of course, since your opponent(s) are also trying to "lose", it can be just as hard as the normal game. Indeed, some game states/hands/etc. may be favorable in both the normal game and the misère game (or unfavorable in both).
Hearts plays around with this in many fashions. For one, while it's a trick-taking game, the goal is to collect the least points, so the easiest way to accomplish this goal is to take as few tricks as possible, which would be this trope in most other trick-taking games. However, you can instead attempt to take all 14 point-scoring cards (the thirteen hearts and the queen of spades), thereby "shooting the moon" and either subtracting points off your score or adding points to everyone else (depending on rules), playing this straight within the conceit of the game. Plus, when the other players realize that an attempt at shooting the moon is happening, one way to stop it is for a player to deliberately take a single heart themselves, a small-scale version of this trope (as ideally they take just that one point and the would-be moon shooter already took the other 25, or can't avoid taking them).
Spades:
- This game revolves around predicting how many times you can play the highest card in a group of four cards. Each group of four cards is called a trick. Bidding nil is when you predict that you won't win any tricks. If you do indeed fail to win any tricks after bidding nil, you gain a hundred points. Winning any trick after bidding nil will make you lose a hundred points. If you bid nil with the ace of spades (the one card guaranteed to win any trick) in your hand, you either Failed a Spot Check or Didn't Think This Through. Variations allowing a blind nil bid (i.e. bidding nil before you even look at your cards, worth double the normal bonus or penalty) take this up a notch, as you're gambling on a combination of having bad enough cards that opponents can't screw you over. Both cases are mitigated in versions of partnered spades where someone who bids nil can pass one card of their choice to their partner (or two if a blind nil bid is made), and the partner gets to pass one (or two) back, but it's still a risky bid regardless.
- Occasionally, a team will intentionally fail to take the promised number of tricks so the other team takes enough bags to incur a penalty. This usually occurs in the endgame, where, if the other team takes the exact number of tricks they bid on, they would win the game.

Video Games

Baldur's Gate II: during the cutscene at the end of chapter 1, the Big Bad Irenicus is seen using his powerful magic to destroy the Shadow Thieves. However, he is in Athkatla, where magic is illegal, and the combat conjures wizard enforcers that strike back and invite to "you will cease your spellcasting and come with us; even if we fall, our numbers are many, you will be overwhelmed". Irenicus accepts to surrender, at the condition that Imoen is arrested too since she cast a magic missile on him. Irenicus knows that he will be brought to the distant asylum of Spellhold, which he can easily take over from the inside and use to set up a more efficient operational base for his plans (which include Imoen as well). And he knows that the player character will do anything to take revenge on him and/or rescue Imoen, falling into his trap.
Final Fantasy X. Operation Mi-ihen early on is a villainous example of one. At first it seems like a Cooperation Gambit between the Maesters of Yevon, the Crusaders, and Al-Bhed to defeat Sin without the use of a Summoner. Utilizing weaponized Machina with the Crusader forces, with the blessing of Yevon's leaders even though it is a terrible taboo and all those participating are excommunicated. It becomes apparent shortly before the operation commences that the Maesters do not believe there is any chance of it working. The result is the utter decimation of Crusader forces and Al-Bhed Machina, leaving spectators and survivors with a sense that straying from Yevon's teachings was their downfall. Auron puts it something to the effect of sending the heretics to die and being left with only the faithful.
In The Legend of Heroes: Trails of Cold Steel, this is Osborne's plan to get rid of the curse of Erebonia for good. By painting himself as the biggest target, he ends up making sure that he would fall so that the source of the curse, who is possessing him because the curse chose him to be his chosen one, will disappear from the world for good. It also involves his son, The Hero, to actually do the deed since Rean's quest in Cold Steel IV is to gather all of the seven divine knights' powers and complete the Great One in order to destroy Ishmelga for good. He succeeds in the Golden Ending.
The Legend of Kyrandia: In Malcolm's Revenge, you end up playing Tic-Tac-Toe against the fish queen, and the only way to progress is to lose (and convince her that she won fairly), or she'll insist on a rematch. Unfortunately she's such a terrible player (the game makes intentionally counterproductive moves) that it's actually a challenge to lose.
Mario Party:
- Sometimes you will want to lose a minigame on purpose. This may seem counter-intuitive... but if you're teamed up with a player who's on the lead in stars and is just short of coins to buy the next one after the minigame, you might want to make them lose by letting yourself be beaten as well. This way your teammate won't get too far ahead on the lead, which is a pretty neat outcome in exchange for declining 10 coins.
- Mario Party 9: One potential outcome of landing on a Bowser Space is having all players take part in a Reverse Minigame. These take an existing minigame, but the goal is to deliberately come in last, such as being the last player to reach the bottom in Chain Event or being the first player to get eliminated in Billistics. The "winner" will receive ten Mini-Stars for their trouble.
Twisting the trope around to the very beginning of the game, Mega Man X5 sees the series Big Bad Sigma launching a spontaneous attack that X and Zero thwart before anything's even really happened. Except he was intending on this, as the body's explosion causes a rapid spread of the very virus that composes Sigma, infection spreading across the Earth and driving Reploids mad, and thus producing Sigma's Maverick forces for this entry without lifting a finger. If that wasn't bad enough, it was also the signal for Dynamo to perform a Colony Drop of the genocided Eurasia space colony, throwing the Earth into its greatest crisis yet.
Metal Gear Solid. In the first installment, Solid Snake's goal is to shut down Metal Gear REX using a special key delivered to him by Otacon. Liquid Snake and his forces had, at this point, spent much of the game trying to retrieve this key from Solid Snake in order to prevent him from shutting down REX. In actuality, the key is the device that launches REX, and Liquid had counted on Solid Snake to make it through his forces and attempt to shut down REX, thus activating it. The reason it counts as this trope is that Liquid thought the device required three keys, and it turns out Solid Snake's key was all three in one^note...and while Solid Snake eventually learned how the key worked, Liquid didn't know anything about it, so he still had to depend on Solid Snake unlocking the launch sequence because Liquid couldn't do it himself.
In Papers, Please, one scripted entrant presents their paperwork as usual, and it's all in order... and then they bribe you with money to stamp their passport with a denial stamp and refuse them entry, as they found better work elsewhere and wants a documented reason to abort their job and come back home. Denying them access will get you the money promised, but your employer will issue a citation for refusing entry to a valid applicant.
In Quest for Glory II, the Evil Chancellor Ad Avis needs a "Hero from the North" to fulfill a prophecy, so he summons elementals and sends them northward specifically so that they'll be defeated by said Hero.
In Town of Salem, the Jester's win condition is to get lynched by the town. The most common tactic to win is to convince the town that you're evil (say, a Serial Killer or Mafia member) and therefore someone who should be lynched, which is game over for literally any other role.
In The Worst Knight, Sir Trihard does not want to marry the princess, and declining outright would be punished by death. He decides to spend his time earning a reputation as a bad knight in order to make the princess not want to marry him.

Visual Novels

Zero Escape Trilogy:
- Zero Time Dilemma retroactively implies that Dio being sent to Rhizome-9 to stop the AB project in Virtue's Last Reward was this. Dio's presence in Rhizome-9 was necessary for the success of the AB project, and Sigma's presence at D-Com, the end result of the AB project, was critical for Delta's plans, and since Delta was the one who sent Dio it's almost certain that Dio screwing up and the AB project succeeding was the outcome Delta wanted.
- Because the story of the trilogy runs off Mental Time Travel, and it's impossible to get the good endings to any of the games without your character learning information from the bad ones and taking that information back with them.

Webcomics

Bad Machinery: A classic real-world Failure Gambit, the idea of "tax scam records" (see below), is referenced in this strip.

Western Animation

Codename: Kids Next Door: In "Operation E.N.D.", the recently turned teenager Chad Dickson, Numbuh 274, tries to send the entire Moon Base hurtling into the sun to prevent the knowledge of his aging out of the KND from leaking. Numbuh 1's quick thinking manages to prevent the plan, and Chad is slated to be decommissioned. Immediately afterward, Cree Lincoln arrives where Chad was being held, culminating a multi-episode Xanatos Gambit to send the Moon Base into the sun, but when Chad reveals he just tried and failed, she immediately gives up and leaves, taking Chad with her. We only learn in the penultimate episode that Chad had known about Cree's plan from the very beginning, and used this gambit to not only save the Moon Base but also become a deep, deep-cover mole in the KND's enemies.
An episode of Garfield and Friends involved Jon's cousin Roscoe attempting to prove he could be successful at something in order to convince his girlfriend to marry him. However, his dimwitted nature and lack of foresight made him a Walking Disaster Area. Garfield eventually set up a scenario that resulted in Roscoe wrecking the living room while he set it up to make it look like Roscoe was a professional demolition expert, convincing Roscoe's girlfriend he could do something right.
Jade Armor: The Crimson Lord pulls one in episode 11 intentionally holding back and losing to Jade Armor to gaslight Kai into believing his lie that Jade Armor is the real villain.
Kaeloo: One episode has Kaeloo, Stumpy, Quack-Quack, Mr. Cat, and Cramoisie playing a game where one person is secretly designated as a "zompire" (a cross between a zombie and a vampire) and the other players must avoid getting bitten by the zompire. Cramoisie is the zompire and she attempts to manipulate Mr. Cat into staying close to her by pretending to be scared. Mr. Cat sees through her guise instantly, but gladly allows her to bite him because then he can use the pretext of being part-vampire to step into a coffin and take a peaceful nap without anyone bothering him.
In the final season of My Little Pony: Friendship Is Magic, this was Discord's plan to help Twilight when she was preparing to take Celestia and Luna's place as Equestria's ruler. Posing as the ancient monster Grogar, he gathered together the Main Six's unreformed enemies into a Legion of Doom and prepped them to attack during Twilight's coronation, figuring that defeating them would give Twilight the confidence she needed to rule Equestria. Unfortunately, he didn't expect the villains to take his teamwork lessons so closely that they'd band together against him and drain him of his magic with the Bewitching Bell before setting out to take over Equestria, making them an actual threat instead of just a ploy.
South Park. In one episode, Satan fights Jesus and intentionally takes a dive after the people of the town have all bet on his victory due to his overwhelming physical advantage. He then reveals that he made a fortune by being the one and only person to bet on Jesus winning, all according to plan.

Real Life

One tax dodge attempted by someone who was more-or-less broke was to sign a note saying they had borrowed a large amount of money, say $100,000, while only really receiving a fraction of this, say $10,000. They then declare bankruptcy on the $100,000. The person who has the note now has a legitimately non-collectible debt and can claim the full $100,000 as a loss on their tax return even though all they really loaned the person was $10,000.
Throwing a sports game by faking incompetence or pain, then cashing in on all the assets your business partner made betting on the other guy. This is one of the oldest tricks in the book, probably ever since losing stopped equaling death on the battlefield. Note that this doesn't really work in the big leagues, as players have a salary that could make a CEO blush, while witnessed by millions of viewers (both in and out of game, so making behind-the-scenes deals is near-impossible), and thousands of sports experts that can spot a fake-out in a split-second.
The concept of "tanking" in professional sports. See, at least in North American leagues, there's a Comeback Mechanic where losing more games in a season means you get better pickings of the new players out of college next year ("the draft"). Therefore, if you know you can't win this year, why not try to do as bad as possible so you get even better draft picks? This is usually done by middling teams that can't get over the hump or bad teams that aren't quite bad enough to net a top pick. Teams have two ways to tank: either not giving full effort in games, or sabotaging an existing roster by cutting and/or trading most of the top-end talent. The first method is usually met by derision by fans and observers but is also fairly rare and difficult to prove. The second method is more accepted, as it can happen involuntarily due to salary cap restrictions, but is liable to turn sour if it doesn't lead to a winning team within a few years.
It's been suspected that Uwe Boll kept making so many bad movies in the late 2000s because of a quirk in German tax law that allowed him to make money on films that failed to turn a profit.
"Tax Scam Records" were records created with no intention of them ever selling, often without the knowledge (let alone the permission) of the artists, as a way of creating fraudulent losses for tax purposes; see this article.
In the 1954 FIFA World Cup, West Germany was about to face favorites Hungary in the group stage. Manager Sepp Herberger rested several key players and played others out of position so they'd lose (and did handily, 8-3 to the Magyars!), but would be at full force for the game against Turkey that would be the knockout qualifiers. Finishing second also guaranteed easier match-ups in the playoffs against fellow group runner-ups, until a Heroic Rematch against Hungary in the final, who - against a German squad no longer holding back - lost their first game in 5 years.
In the Chinese professional League of Legends scene, there was a rather infamous (and hilarious) incident in 2015 dubbed "Oscar Night", a best-to-3 series between Invictus Gaming and LGD Gaming that was their last before playoffs. Neither team wanted to win the game, as they were fighting for a seed that would pit them immediately against Edward Gaming, who was at the time considered nigh-unstoppable— the loser would still be in the playoffs, but would only face Edward Gaming at the grand finals at the most. Because teams couldn't simply forfeit the match, they were forced into a very awkward contest to make the absolute worst plays possible without making it obvious that they were trying to lose, and unsurprisingly, it spiraled into a complete forkin' mess that had to be stopped by referees once the kill scores reached "total bloodbath" levels yet it became clear that both teams were avoiding closing the actual game. Unsurprisingly, the next split restructured the tournament seeding and made it so a situation like this was impossible^note.
There are a handful of seemingly counterintuitive business strategies where products are sold at a loss that end up leading to other forms of stimulation that result in more long-term profitability than if they just had a higher starting price. The "loss leader" strategy involves selling a product at a loss in order to attract (or "lead" in) customers to other products with higher profit margins, with common examples being grocery stories and supermarkets (ever wonder why so many stores place cheap bananas at the entrances? This is why!). The "razor-and-blades" model involves selling a primary item at a cheap price in order to increase sales of a complementary good; the name comes from an apocryphal catchphrase about shaving razors, "Give 'em the razor; sell 'em the blades", and it's also found with other products like video game consoles (console manufactures often sell consoles at a loss, but make up through the sales of video games that they license for release).

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