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Win Your Freedom

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To any victim of long-term incarceration, being set free from it is the ultimate MacGuffin. Of course, it won't come cheap, but when the alternative is to rot and die in captivity, they'll gladly risk their life on whatever No OSHA Compliance Death Course is required of them to get it.
The favorite motivational carrot of Boxed Crooks and Condemned Contestants, since they're already locked away, but the threat of incarceration can be used preemptively so long as the victim is already powerless to resist. Any kind of Deadly Game or Gladiator Games is likely to have this as the prize since most people wouldn't risk their life without an appropriately large reward. Likewise, the Most Dangerous Game has life as the reward.
One common variant would be when it's the victims friend or family member whose freedom they're trying to win. Shows great dedication when the victim could just turn and walk away and leave them to their fate.
Since the kind of people who are locked up are typically not someone the captors want to let out, not to mention that doing so would mean losing their services, it's common for them to sabotage the victims attempts at fulfilling the terms of the agreement, just changing them as needed, or lying and killing them. If anyone asks, the previous "winners" were Released to Elsewhere. Just about every Evil Overlord does it at some point, typically making the challenge Unwinnable by Design. Of course the hero wins, only to realize he was being baited and breaks free instead.
Forced Prize Fight and Death Course often go hand in hand with this. Practically every Closed Circle adventure game ever.
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DBTropes
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In This Immortal, when captured by the Kouretes, the group of protagonists is given the option that one of them fight the Dead Man to win all of their freedom. Moreby is very confident that whoever fights will lose, as that's what always happens.
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Ross's Game Dungeon: While reviewing Armed & Delirious, Ross proposes that the prison system be changed so that instead of criminals being sentenced to X number of years in prison, they should instead have to stay in prison for as long as it takes them to win their freedom by beating a brutally difficult gaming challenge. For instance, the punishment for assault would be to complete a no-death run of Super Meat Boy, and the punishment for murder would be to beat Armed & Delirious with no hints or walkthrough of any kind (an Impossible Task considering the game's utterly incomprehensible Moon Logic).
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Megara in Disney's Hercules will regain her soul from Hades if she helps him find Hercules' weakness. Naturally, she ends up falling in love with him - which gives Hades the leverage he needs anyway. Hercules gives up his Super-Strength for twenty-four hours in exchange for Meg's freedom (and, crucially) safety. Hades agrees, in an unspoken Magically-Binding Contract.
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Between The Winter Queen and The Turkish Gambit, Erast Fandorin fights in the Russo-Turkish War and is taken as POW by the local governor. However, when he accidentally discovers information crucial to the Russian army, he wins his freedom in a game of checkers (because he is Born Lucky and never loses bets, even when they don't actually involve games of chance) and leaves.
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In The Phantom Menace, Qui-Gon Jinn makes a bet with Watto that if Anakin wins the podrace, then Watto must give Anakin to Qui-Gon. When Anakin wins, Qui-Gon immediately frees him and takes him to the Jedi Academy.
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Togainu no Chi: After being accused of murder and threatened with a life sentence, Akira agrees to join a bloodsport called Igura to challenge the game's undefeated champion, Il-Re. He is promised that if he kills Il-Re, the charge against him will be dropped. He does not win.
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AI Programmer Sofia Mendes has to book enough programming jobs to be released from her "intellectual prostitution" by her broker in The Sparrow.
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In The 100, when people were riding out the second nuclear apocalypse in an underground bunker, they developed a system of justice in which people convicted of a crime were sentenced to gladiator combat with one simple rule: "Be the last." The winner could earn a pardon; the losers were dead. It also helped with the food supply situation.
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The Garlean Empire in Final Fantasy XIV conscripts soldiers from conquered territories to feed their war machine and prevent any uprisings. They offer an incentive for service by promising full Garlean citizenship to the soldiers and their families if they provide twenty years of service in the military.
The Coliseum in Uldah is another variant on this - gladiators who gain the favor of the Sultana or certain factions are appointed to military or royal guard positions. Specifically, this is how Raubahn became the general of the Immortal Flames.
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In old Draenor in World of Warcraft, an ogre city kept orcs as slaves and gladiators for their amusement. They promised freedom to any orc who could kill one hundred opponents in the ring. One orc, Kargath, met the challenge, but found that freedom to be a lie and was locked up in a deep prison with those other orcs who met the quota. Kargath and the orcs cut off their hands to escape their bonds, grafted weapons to their stumps, murdered the ogres, and became the Shattered Hand Clan.
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Freedom Wars: You (and most people living in the Panopticons) have been sentenced to one million years' imprisonment, but you can work off that sentence by volunteering to take up arms against robotic monsters and other Panopticons.
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Beyond Temptation: Demons who abandoned Lucifer during his Rage Against the Heavens are imprisoned in boxes. Their only chance for freedom is to tempt enough souls.
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On My Name Is Earl when Earl was incarcerated the warden kept giving him "time off" coupons for various good deeds, but when Earl earned enough of them to get out the warden reneged.
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Miguel Dominguez in Day Break (2006) was let out temporarily so that he could commit a murder.
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Subverted in Thor: Ragnarok. The Grandmaster of Sakaar claims that anyone who can best his "champion" in the Gladiator Games will win their freedom. Not only is his champion the nigh-invincible Hulk, but the moment it looks like Thor's going to win, the Grandmaster goes back on his word and activates Thor's Shock Collar.
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Mortal Kombat is this on a much larger scale. The tournament determines whether or not Earth Realm will be spared an invasion from Outworld.
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In Berserk, when Guts decided to leave the Band of the Hawk to find his own dream so he could be a true friend and peer to Griffith, Griffith didn't take it well at all. He reminds Guts that he won Guts' service by beating him in a swordfight years ago and declares that Guts would have to win his freedom with his sword. As they get ready for a rematch, Griffith realizes that the strike with the best chance of defeating Guts in one blow also has a high chance of killing him. Griffith decides it doesn't matter, having gone Yandere for him over time. All for naught, since Guts is strong enough to break Griffith's sword with one strike, defeating him effortlessly.
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In the ThunderCats (2011) episode "The Pit", prisoners of the Dogs are set free if they can win one hundred gladitorial fights in a row.
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In Girl Genius the Castle Heterodyne prisoners are all trying to earn enough points that the bombs strapped around their necks are disabled and they are allowed to go free. This happens very rarely as the castle usually kills prisoners before they earn enough points.
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In Ferdinand, the bulls believe if they defeat the matador they will be set free. Only when Ferdinand enters the rancher’s house does he learn that the bull never wins. Ferdinand, however, does win his freedom by not fighting the matador and winning the crowds’ respect.
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Sawyer in Lost ironically bypassed most of a six year sentence by agreeing to con an inmate into revealing the location of a large sum of money he stole.
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Radiant Historia: Stocke has to do this by trampling through a set of gladiators.
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Assassin's Creed Origins: Two different quests in Libya deal with former gladiators who were promised freedom after winning a certain amount, only for their masters to renege because their fights earned so much money, at which point the gladiators made a break for it anyhow. In the first, the slave's owner doesn't even give a rat's ass about the escaped slave, just the fact he stole the man's favourite sword.
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Near the end of Warcraft 2016, Anduin Lothar is challenged to Mak'Gora by Warchief Blackhand. After Lothar wins the duel by killing Blackhand, the Orcs allow him to leave on his gryphon, carrying the body of King Llane with him. Gul'dan demands that the Orcs kill him instead, but is told that Lothar has won his freedom through the victory in the Mak'Gora and that he would lose the Horde's support if he did anything to keep Lothar from leaving.
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In Gladiator, Maximus pretends this is his motive for fighting. In reality, he wants to get close enough to Emperor Commodus to kill him.
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In the Dressrosa arc of One Piece, this is part of the legendary gladiator Kyros's backstory. As a teen, he killed two people in cold blood as revenge for his own dead friend, and was arrested as a result. King Riku, not wanting the youth's life and fighting prowess to go to waste, offered him a deal: he'd give the boy his freedom back if he could win 100 battles at the Corrida Colosseum tournament. Kyros effortlessly won those battles, but kept going as the townspeople still hated him for his crime. He eventually did stop, at 3000 victories, and earned himself not just his freedom but also a place as captain of the Dressrosan army and bodyguard for King Riku and his daughters.
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The story of Joseph in The Bible has this. Joseph was in jail on (false) rape charges, and Pharaoh was having some bad dreams that no one could interpret. Pharaoh eventually wound up talking to Joseph, who said that the dreams were a prophecy about an upcoming famine and suggested that Pharaoh appoint a wise man to take charge and see Egypt through it. Pharaoh was so impressed that he decided Joseph was just the guy for the job.
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Discussed in the ending credits of Portal 2
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Recurring in Spartacus: Blood and Sand, related to reasons in Real Life, below:
Earliest (chronological) use, Gannicus is freed at the end of the games to inaugurate Capua's new Arena, as part of a Batman Gambit by Batiatus' rival to deprive him of the best gladiator in the city (and perhaps the Republic).
Spartacus agrees to channel his passion into victories in the Arena, under the condition that Batiatus will find and procure his wife, and the two of them can eventually be freed together. This doesn't work precisely the way Spartacus had hoped.
Invoked by Spartacus' friend Varro. A Roman citizen who'd sold himself into slavery to cover his gambling debts, he hopes to win enough money fighting in the Arena to cover the remainder of his debts and earn his freedom to be reunited with his (still free) wife. This also does not go according to plan.
Barca earns enough money betting on Spartacus and Crixus' victory against Theokoles to buy freedom for himself and his lover, Pietros. Barca makes the mistake of pressing Ashur too hard for his winnings, so Ashur sees to it this also goes awry.
Crixus and Spartacus again find themselves at cross-purposes briefly in the first season finale, as Crixus wants to remain a gladiator, earn his freedom, then seek out his lady love, fellow slave Naevia, while Spartacus wants to lead a slave revolt.
And of course, the bulk of the series is about the slaves trying to win their freedom in a way Rome had never intended.
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In The Rock, FBI Director Womack promises Jon Mason that if he helps them infiltrate Alcatraz, then they will set him free. Womack has no intention of actually setting Mason free, but Agent Goodspeed pretends Mason was killed and vaporized during the operation, so Mason can gain his freedom.
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The Penal Legions in Warhammer 40,000 are groups of condemned criminals sent on suicidal missions they wouldn't even send Imperial Guard to do, with a promise of forgiveness if they die, and freedom on the very, VERY small chance they live.
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Shin Megami Tensei III: Nocturne - Wanna prove your "innocence" in front of the Mantra Army Court? Get ready to punch out Thor.
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In Midnight Tides, book five of the Malazan Book of the Fallen, the Drownings are a popular public spectacle in Letheras in which condemned criminals who couldn't pay the required fine to win their freedom can do so by trying to swim across the canal with a sack full of coins strapped to their back. The amount of coins depends on the crime. Since few ever manage to make it across, wagers are usually made about things like the distance, number of strokes or the manner of drowning. note The sacks of coins have ropes attached to allow for them to be pulled back out of the canal, while the bodies get dumped right back in.
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So far, Last Res0rt looks like it's playing this straight, for the criminal contestants. They've all been offered their freedom, if they survive (and, one assumes, win) the games. Cypress Vaeo, one of the people behind the show's creation and their 'face', has this to say to critics:
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In the Criminal Minds episode "Legacy", the barefoot victim wakes up in a house of horrors and is told that if she can escape by sunrise, she can have her freedom (and her shoes).
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The Stainless Steel Rat: when the teenage Jim diGriz and his mentor, The Bishop, are double-crossed and sold into serfdom in a world based on the nastier aspects of medieval Italy, diGriz fights his way out of slavery and sets into motion a series of events that cause the dissolution of condottieri society. This begins with a nasty fight with a slave-bully to establish his place in the hierarchy.
In later life, diGriz helps a planet with a suspiciously Latin American/Francoist Spain set-up to throw off its dictatorship: this time the battle to the death takes the form of the universe's most crookedly rigged election.
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Jonny Quest episode "Dragons of Ashida". Mad Scientist Dr. Ashida refuses to let the Quest team leave his island, but he promises to let them go if Race Bannon defeats his servant Sumi in a judo match.
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The premise of Alias Smith and Jones. The reformed outlaw heroes will get a pardon once they convince the governor that their Heel–Face Turn is real.
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We Who Are About to Die: A staple in Gladiator Games, and thus a staple here. Aspirants with the Slave origin aim to gain enough Fame, and enough sway with the Patrons hosting the gladiatorial games, to be released from servitude. This is easier said than done, as their starts are rough and they must give away half their earnings, but they do have one advantage: The longer they survive, the more the crowd enjoys their presence (they have a thing for unlikely champions), so they get more Fame than usual. Criminal Scum Aspirants often seek the same, surviving long enough to get a pardon, but while they do have a better time (and don't need to give away their money) the crowd tends to dislike them.
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Win Your Freedom
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In Undead Friend the main characters are trapped in a Deadly Game and the only way out is to earn enough points and challenge the people in charge during a specific event in the year. If they don't play they get erased from existence. So the story centers around the main characters trying to get free of the game.
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Win Your Freedom
 Win Your Freedom / int_e3b8885
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A Funny Thing Happened on the Way to the Forum: Almost everything Pseudolus does is because his master, Hero, has offered Pseudolus his freedom in exchange for helping Hero win the heart of Philia, a "courtesan" in the house of Marcus Lycus.
 Win Your Freedom / int_e3b8885
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Win Your Freedom
 Win Your Freedom / int_f2495e2b
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In The Slammer, the prisoners have to win their freedom by being the most popular act in the Freedom Show.
 Win Your Freedom / int_f2495e2b
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Win Your Freedom
 Win Your Freedom / int_fbf28b9d
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The Warden of the Zufu prison in Lupin III: Dead or Alive tells the prisoners they have a chance to escape the jail. They have five minutes to run before the guards start Hunting the Most Dangerous Game.
 Win Your Freedom / int_fbf28b9d
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Win Your Freedom
 Win Your Freedom / int_fcf43f47
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The very premise of the Fighting Fantasy book, Trial of Champions. Right in the opening paragraph, you were Made a Slave and purchased by Lord Carnuss, a ruthless overlord who puts you and forty fellow slaves through a series of Gladiator Games; should you win, you'll then be drafted into the titular annual Trial. Completing it earns you a chance to fight Carnuss to a Duel to the Death to avenge your fellow slaves, your final victory which leads to your freedom as well as a life of wealth and luxury.
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The following is a list of statements referring to the current page from other pages.

 Win Your Freedom
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A Slave to the Index
 Win Your Freedom
processingCategory2
Crime and Punishment Tropes
 Superboy (1994) (Comic Book) / int_c1d9d74c
type
Win Your Freedom
 Hercules / Disney / int_c1d9d74c
type
Win Your Freedom
 Danganronpa: Dead on Arrival / Fan Fic / int_c1d9d74c
type
Win Your Freedom
 Dreadnought Despair (Fanfic) / int_c1d9d74c
type
Win Your Freedom
 Escape The Ronpa (Fanfic) / int_c1d9d74c
type
Win Your Freedom
 Fallout: Equestria - Murky Number Seven (Fanfic) / int_c1d9d74c
type
Win Your Freedom
 More Than Human (Fanfic) / int_c1d9d74c
type
Win Your Freedom
 The Violet Demon (Fanfic) / int_c1d9d74c
type
Win Your Freedom
 Death Race / int_c1d9d74c
type
Win Your Freedom
 Gladiator / int_c1d9d74c
type
Win Your Freedom
 Kaiji: The Ultimate Gambler / int_c1d9d74c
type
Win Your Freedom
 Series 7: The Contenders / int_c1d9d74c
type
Win Your Freedom
 Soldier Boyz / int_c1d9d74c
type
Win Your Freedom
 The Phantom Menace / int_c1d9d74c
type
Win Your Freedom
 The Running Man / int_c1d9d74c
type
Win Your Freedom
 Thor: Ragnarok / int_c1d9d74c
type
Win Your Freedom
 Fighting Fantasy / int_c1d9d74c
type
Win Your Freedom
 Midnight Tides / int_c1d9d74c
type
Win Your Freedom
 War of the Worlds: Global Dispatches / int_c1d9d74c
type
Win Your Freedom
 Wings of Fire / int_c1d9d74c
type
Win Your Freedom
 ExitPath
seeAlso
Win Your Freedom
 Mario4812LikedTropes3
seeAlso
Win Your Freedom
 War of the Triple Alliance
seeAlso
Win Your Freedom
 Battle Beast (Music) / int_c1d9d74c
type
Win Your Freedom
 The Freewheelin' Bob Dylan (Music) / int_c1d9d74c
type
Win Your Freedom
 Danganronpa: Return to Despair Academy (Podcast) / int_c1d9d74c
type
Win Your Freedom
 AmnesiaER
seeAlso
Win Your Freedom
 Celestial Despair: The Cosmic Confluence in Conspiratorial Confinement (Roleplay) / int_c1d9d74c
type
Win Your Freedom
 Cynismi (Roleplay)
seeAlso
Win Your Freedom
 Demonic Despair (Roleplay) / int_c1d9d74c
type
Win Your Freedom
 FatalFrenzy
seeAlso
Win Your Freedom
 Peak of Hope (Roleplay) / int_c1d9d74c
type
Win Your Freedom
 Revival Of The Fittest (Roleplay) / int_c1d9d74c
type
Win Your Freedom
 Solar City (Roleplay) / int_c1d9d74c
type
Win Your Freedom
 Terror Across The Stars (Roleplay) / int_c1d9d74c
type
Win Your Freedom
 The Ouroboros Project (Roleplay) / int_c1d9d74c
type
Win Your Freedom
 Day Break (2006) / int_c1d9d74c
type
Win Your Freedom
 Lost Girl / int_c1d9d74c
type
Win Your Freedom
 My Name Is Earl / int_c1d9d74c
type
Win Your Freedom
 Zorro (1990) / int_c1d9d74c
type
Win Your Freedom
 Exit Path (Video Game) / int_c1d9d74c
type
Win Your Freedom
 Fist of the North Star: Lost Paradise (Video Game) / int_c1d9d74c
type
Win Your Freedom
 Freedom Wars (Video Game) / int_c1d9d74c
type
Win Your Freedom
 Jedi Knight: Jedi Academy (Video Game) / int_c1d9d74c
type
Win Your Freedom
 Shin Megami Tensei III: Nocturne (Video Game) / int_c1d9d74c
type
Win Your Freedom
 The What-Iffers in: Final Fancy (Video Game) / int_c1d9d74c
type
Win Your Freedom
 We Who Are About to Die / Videogame / int_c1d9d74c
type
Win Your Freedom
 Dangan Ronpa (Visual Novel) / int_c1d9d74c
type
Win Your Freedom
 Iron Lung: The Machinima (Web Animation) / int_c1d9d74c
type
Win Your Freedom
 SuperThings (Web Animation) / int_c1d9d74c
type
Win Your Freedom
 Ross's Game Dungeon (Web Video) / int_c1d9d74c
type
Win Your Freedom
 Welcome To Sanditon (Web Video) / int_c1d9d74c
type
Win Your Freedom
 A Tale of Two Rulers (Webcomic) / int_c1d9d74c
type
Win Your Freedom
 Basic Instructions (Webcomic) / int_c1d9d74c
type
Win Your Freedom
 Asterix Versus Caesar / int_c1d9d74c
type
Win Your Freedom
 Jonny Quest / int_c1d9d74c
type
Win Your Freedom
 The New Adventures of Jonny Quest / int_c1d9d74c
type
Win Your Freedom