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Sympathetic Slave Owner

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While most (modern) stories that depict slavery portray it as unambiguously evil and slavers are generally the worst of villains, there are a lot of different approaches one can take when depicting individual slave owners. Sometimes, owning slaves is portrayed as a sign of being a crappy person, or even crossing a Moral Event Horizon. Other times, however, a writer will portray slaveholders in a more favorable light by making them act benignly towards their "property". That is, in essence, what the trope is about — slave owners that appear benevolent towards their slaves, or at the very least aren't as bad as they could be.
It usually comes in one of two variants:
The character doesn't see slavery as immoral and willingly uses it to their own advantage, but they extend a level of kindness towards their slaves. There may be several reasons for this:
They were just raised in a culture or environment in which slavery is seen as normal, and thus don't see much problem with it themselves. It is a common way to portray a historical character who owned slaves without them appearing too unsympathetic.
They do derive some amount of pleasure from their power over the slaves, and may mess around with them and act condescendingly towards them - but deep down, they do care for the slaves, and would never do anything actually harmful to them. They would also demonstrate Hypocritical Heartwarming if someone else mistreats their slave. Expect overlap with Power Dynamics Kink and (if the slave owner is an older female and the slave is a younger male) Mistress and Servant Boy.
Their slaves used to be Jerkasses or outright villains, and they see slavery as a way of reforming their character and changing them for the better. This often verges on Good Is Not Nice territory.
The character does not approve of slavery and only owns slaves because of necessity. It could be that they cannot legally free their slaves, that the slaves are bound to them by some sort of magical contract, or that they simply see it as a sad necessity. They may own the slaves to protect them from a worse fate. They are likely to be courteous to the people they own and will not resort to using force unless absolutely necessary, if ever. A few may even adopt the persona as a cover for being members of an Underground Railroad-esque organization.
Slaves owned by such a person often exhibit Happiness in Slavery, but it is not a given; whereas some will be perfectly happy in their situation, others will not be satisfied with such an arrangement and will yearn for freedom all the same. The latter attitude ties in with a common deconstruction of this trope — if the slave owner is really as benevolent as they like to believe/claim they are, why won't they just free all their slaves? If the slaves are actually happy in bondage, they would keep working for their master even after being freed, right? It's not as though they have their own plans and desires.
Super-Trope of Hero's Slave Harem, in which the slave owner is romantically involved with slaves.
Sub-Trope of Benevolent Boss. Contrast Slavery Is a Special Kind of Evil and Human Traffickers. Compare Nice to the Waiter, when a character is acting politely to working-class members rather than their own slaves (or both), and Honest Corporate Executive, another sympathetic portrayal of the higher-ups who may or may not be slave owners. And while it is considered somewhat discredited in realistic settings, it's still very much in use in fantasy settings, especially when the slave is an ordinary human, and the master is a mage or a supernatural being (one of the reasons is that it fits the religious archetype of the relationship between humans and God).
No Real Life Examples, Please! While treatment of slaves varied somewhat throughout history and there likely were some slave owners who could be considered benevolent, we are not here to discuss the morality of historical people and societies, especially since we have no way of asking the slaves how they really felt about their owners.
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Kelly The Roman Warrior: The narrator admits that Kelly's father, the "Ceaser" who rules all of Rome, does own slaves as an instance of Deliberate Values Dissonance, but stresses that he's nice to them.
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South Park: The Fractured but Whole: Played for Laughs and completely defied in the "Bring the Crunch" DLC. After beating the final boss, Mintberry Crunch reveals that the alien they just fought was an escaped slave of his. Jimmy tries to rationalize how being a slave owner can add complexity to a hero, only for the Creepy Gas-Station Attendant to come by and tell him that he should probably drop that line of thought as soon as he can.
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The Rising of the Shield Hero: Iwatani Naofumi finds himself summoned to a fantasy world as one of four legendary heroes, but he turns out to be the "Shield Hero", the least-respected of all the heroes to the point that when a two-faced party member accuses him of trying to rape her, everyone believes her immediately. The shield's lack of any offensive abilities whatsoever makes him unable to level up on his own, but the experience with his traitorous former comrade makes him unable to trust anyone else. As such, he settles for buying slaves who are magically-bound to obey his commands, can't betray him, and can fight on his behalf. Though this does little to quell public opinion about him (especially since his slaves are cute young girls, causing everyone to jump to conclusions), his first slave, Raphtalia, quickly learns that he's a kind and decent master, to the point that she begins to fall in love with him. Moreover, as the story progresses, Raphtalia and Filo quickly become slaves in-name only, and Naofumi ends up regarding them as his daughters. Raphtalia is eventually freed when she becomes the Katana Hero, and from then on fights alongside him as his equal.
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Patternmaster is set in a Feudal Future with a Supernatural Elite of psychic Patternists owning mind-controlled "mute" Muggle slaves. Jackson the muteherd is respected for being compassionate and attentive towards the mutes in Coransee's House, even when Coransee allows the more sadistic House members free rein with them.
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Adventures of Huckleberry Finn:
According to Huck, Mary Jane Wilks is a compassionate girl to her family's slaves. For example, she was crying when one slave had to be sold and thus separated from his family, especially his children.
Zig-Zagged with Huck's adoptive mother the Widow Douglas. She's said to treat her house slave Jim reasonably well, but he runs away, joining up with Huck when she decides to sell him to another family and he can't be assured of similar treatment. She ultimately frees Jim in her will.
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The Phantom Menace: Watto's no saint, but he's comparatively a lot nicer to his slaves than most other slave owners depicted in Star Wars (such as Jabba the Hutt, who sexually harasses his slaves and feeds them to his rancor if they displease him). He lets Shmi and Anakin have their own home which, while nothing fancy, seems comfortable enough and pretty much lets Anakin do what he wants provided he completes his work. He also appears to have a soft spot for them; he seems genuinely sad to see Anakin go when Qui-Gon wins his freedom and is happy to see him again a decade later in Attack of the Clones, calling him "little Ani". When he had to sell Shmi due to money troubles, he also made sure she'd be bought by someone who would treat her well, and is tickled that her new owner wound up freeing and later marrying her.
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Captive Prince:
Slavery is a respected institution in Akielos, with slaves elevating obedience to a high art and owners expected to provide perfect treatment and care. As Prince, Damen exemplified that ideal and was highly thought of for his use of Sex Slaves — even by the slaves. After being Made a Slave and regaining his freedom, he comes to question the institution and takes steps towards ending it.
Erasmus the pleasure slave and Ambassador Torveld represent the "ideal" master-slave relationship. They fall head over heels for each other at first meeting; both are happy for Torveld to become Erasmus' owner; and they become the Beta Couple of the first book.
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From the Dark Sun novel series, The Prism Pentad, Agis Asticles starts out as one of these. While slightly condescending, he genuinely has the best interests of his slaves at heart, treating them well and fairly, as opposed to the vast majority of other slaveholders in the series. Part of his Character Development, however, is recognizing that well-treated or not, a slave is still a slave, unable to even argue with their masters will, and he quickly frees them all when he has the chance.
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Guardians of the Flame: Baron Zhell Furnael, despite slavery's evil being a main theme, is portrayed as a kind, fair man despite being a slave owner. He even has his family live as they do during a brief part of the year, to appreciate their work. Karl tries to have him free all his slaves, but he doesn't get it-slavery is so ingrained it's just taken for granted among most people. He does adjust easily when slavery is abolished though, likely due to his relative benevolence.
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Quo Vadis:
Petronius treats his home slaves relatively well and is a lenient master. Eunice, a Greek slave and a great beauty, falls in love with him and finds Happiness in Slavery. She is later elevated to a position of Petronius' lover, though she stays his slave.
Marcus Vinicius starts treating his slaves better when he falls in love with a Christian barbarian princess Lygia (raised in a Roman household as a hostage, but she was like a daughter for her new family) and hears about Christian ways and their philosophy.
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Vikings sometimes portrays slaves as servants but at times we are reminded that slaves were taken as spoils during their raids. Ragnar Lothbrok takes a Saxon monk Athelstan as his slave and treats him relatively well, even trusts him enough to let him take care of his children and his farm when he and his wife go on a raid. Athelstan points out that most slaves in Kattegat are treated worse than dogs. Ragnar learns the Saxon language from Athelstan and he later considers him his dearest friend.
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The Tempest: The magician Prospero has two slaves, the air spirit Ariel and the savage Caliban. Ariel was initially saved by Prospero from a Fate Worse than Death (being trapped inside a pine tree), and eventually Prospero set him free. As for Caliban, he was initially a villainous creature who even attempted to rape Prospero's daughter Miranda; however, after many years of servitude, he repented, and was probably also granted freedom.
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In 1776, Thomas Jefferson wants to add abolitionism into the Declaration of Independence and rebukes the Southern representatives who won't entertain the idea. One of them points out that Jefferson himself owns slaves, and Jefferson stiffly replies that he is planning to free them. This isn't elaborated on and Benjamin Franklin eventually convinces the rest of the Declaration Committee to let the matter drop in order to pass the Declaration. (Historically, Jefferson never freed his slaves, and Franklin was one of the first prominent abolitionists.)
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Dragon Age: Inquisition: If the Inquisitor recruits the Templars, the storyline eventually leads them to meet Magister Erasthenes, who formerly owned The Dragon Calpernia. A side story Paying the Ferryman shows him being somewhat kind towards Calpernia, even teaching her how to control her magic instead of disposing of her or punishing her for her outbursts. Downplayed as Calpernia still has little sympathy for Erasthenes, resenting him for never fully mentoring her, and off-handedly recalls being beaten at multiple occasions.
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In the Tamuli sequel series to The Elenium, the Proud Warrior Race Woman Mirtai was Made a Slave at age eight in a raid, killed her first owner, and was inherited by his nephew. To her relief, the nephew got her exonerated for the killing, treated her as a trusted friend, and taught her the local language. She even avenged his death when he was killed by an ex-lover and speaks fondly of him years later.
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The Fourth Wise Man has a slave, Orontes, who gently bemoans his status, but is generally treated kindly by his master and eventually freed.
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Overlord (2012):
Ainz' underlings consider him a Physical God in every aspect and only want to serve in any way possible (and can't imagine he was ever a human, a species most of them have ingrained hatred for). If anything, they resist his attempts to improve their lives (giving them salaries and vacations) because they deem themselves unworthy. In one case, he finds that the guards assigned to his rooms are there 24 hours a day. He tells them to get some rest and is furious with the underling who assigned them there but stops when he sees the guards clearly consider it a Bewildering Punishment (they have an item that removes the need for sleep in the first place).
The Lizardmen subjugated by Nazarick wear Slave Collars, but seem well-treated by their standards (Ainz resurrected their tribal leaders at Cocytus' request, feeling they could better serve Nazarick).
After Ainz (accidentally) gets the Baharut Empire to submit to him, the Empire is technically his to command... but the only thing that's really changed is that Nazarick's inexhaustible undead armies now defend its borders, multiple races live together in his lands, and the Emperor can now deal with every complaint the nobles have with "take it up with Ainz", which does wonders for his stomach ulcer and stress levels.
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Death March to the Parallel World Rhapsody: Satou is summoned to another world where slavery is common. As a game programmer stuck in an RPG Mechanics 'Verse, as well as gaining a nigh-infinite amount of experience and leveling points, he is able to adjust to this world and emerge as a great and powerful man. One of his first acts is to rescue three demihuman slaves from a cruel master and then buy them himself when they make it clear that they'd like to stay with him (beastfolk are targeted by Fantastic Racism, and having a kind human owner is safer than being freed outright). At the same time, a pair of half-sisters sold into slavery also coerce their way into his service. One of the half-sisters did this because she was specifically hoping that Satou would use her as a Sex Slave since she fell in Love at First Sight. Unfortunately for her, Satou refuses to sleep with any of his slave girls, even when they clearly desire it, because A) most of them are too young (he prefers women his own age and usually hires prostitutes when they visit towns) and B) he feels that it would be an abuse of his position.
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The Vipers Scheme:
Implies with Anereth. He and his family are better than the other slave owners we see by a mile. He has never acquired a slave on purpose, and if he could have freed them or sold them without putting them into a far worse situation, he probably would have. However, he's also incredibly ambitious, and with slavery being such a deeply ingrained institution in his society, it's unlikely he'll speak out against it, whether he believes its immoral or not. He's also not above manipulating a slave in his power to get what he wants, though he does aim not to be cruel about it.
Anereth's sister. Anereth believes that, when she begins to understand that other slave owners are not like her and are, in fact, committing atrocities on a regular basis, she's likely to become an abolitionist.
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Saints Row: The Third: One mission results in a Morton's Fork where you rescue a bunch of girls who are being forced into prostitution by a rival gang. At the end of the mission, you're given two choices: You can sell the girls back to the rival gang for profit, or you can employ the girls as prostitutes for your own gang. There is no freedom for the women who were forced down this path against their will. However, if you choose to keep them, Zimos informs you that he treats his hos like humans, allowing them to unionize and live otherwise normal lives.
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TwoKinds: Eric is a slave trader who starts to develop second thoughts about his choice of profession over the course of the comic. It helps a bit that he thinks of one Keidran slave his family has had since he was a kid as his little sister (and she has a crush on him).
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Hayven Celestia: A few of the sourang slaveowners in Fair Trade are portrayed somewhat sympathetically, especially in contrast with the downright sadistic krakun. Tikkatikkachitter, Kanti's first sourang owner, revives him after he's stabbed by Saquel, before claiming him as her slave; she also allows her slaves to visit their home tribes when practical and doesn't punish Kanti for his escape attempts, just make it clear that she knows about them. Kanti's second sourang owner, Tittichitterti, gives him even more free reign, to the point of trusting him to go on trade missions to other sourang colonies, believing him when he warns him of his nephew's plans to murder him for the inheritance, and establishing contact with Kanti's tribe as a reward for his help.
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In Tsumiko and the Enslaved Fox, Argent, a supernatural creature, is enslaved via a generational bond to a certain bloodline, and this trope is explored with some of his mistresses.Tsumiko, the titular heroine, is the second type, who only accepted Argent's magical bond because it was the dying wish expressed in her predecessor's letter to her, because Michael, Argent's caretaker and best friend, assured her Argent would die if she did not, and because Argent did not actually refuse to consent when she pressed him, although he does not give affirmative consent. She avoids giving Argent commands, willingly frees him from any previous restrictions that he brings to her, and willingly joins the "secret plot" to free him. Nevertheless, Argent refuses to show any signs of Happiness in Slavery and outright tells Michael that responding gratefully to Tsumiko's kindness would just make her and others believe that his situation is acceptable, when it completely isn't. This is further explored with Argent (and Ginko)'s complex relationship with Amy, who was Argent's kindest mistress prior to Tsumiko, and seems to have been the first type. She gave Argent a comfortable existence as "family butler" and inflicted none of the horrors that many of her predecessors did, but she still violated Argent's personal autonomy in many small ways (like forcing him to accompany her yearly to England, despite him being openly harassed by her husband's relatives, forcing him to allow her in his private spaces, and to reveal some of his secrets to Stu) and kept him as a slave. Ultimately, Argent chooses to forgive her after her death, accepting her choice of Tsumiko as her successor to be her gift to him and an expression of a better self than her actions were able to be. Ginko, on the other hand, never forgives Amy or any of his father's other mistresses, and the narrative presents this as a valid choice as well.
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In the novel Atar Gull, the plantation owner Mr. Wil is considered a "good master" (even by the escaped slaves on the island) because he only applies half the legal punishment to his slaves (and as a result his slaves last longer and are less inclined to revolt), and is complimented on his humanism by other plantation owners. But he's still a slave owner, responding to the news that one of his slaves' children has gone missing with anger because negro children sell better or getting rid of a slave too old to work by accusing him of theft and collecting the reward. Unfortunately, that old slave was Atar-Gull's father, and he proceeds to get the most thorough revenge he can by poisoning Wil's livestock and slaves, murdering his daughter, and taking care of him for years after Wil is reduced to being a mute paralytic and gloating about his revenge at every opportunity.
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In Doctrine of Labyrinths, Felix casts the obligation d'ame on Mildmay in large part to keep him protected in the Mirador, as the contract makes them as one legally. But it still makes Mildmay his slave.
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The Stormlight Archive takes place on the world of Roshar, where slavery is a part of everyday life and only Kaladin really objects to it. The other main cast members, and especially Dalinar Kholin treat slaves respectfully, Dalinar even giving up his magic sword to purchase the lives and freedom of forty slaves previously used as arrow-fodder. Priests are also enslaved on this world to prevent their ever gaining political power again but seem to retain a great deal of freedom to speak their minds.
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Rai Kirah: Durgan, the master of slaves for the Derzhi summer palace, is portrayed as a Reasonable Authority Figure who ends up building a rapport with the enslaved protagonist Seyonne. He's entirely loyal to the institution, but takes other Derzhi to task for their gratuitous cruelty, tries to keep the slaves in good condition, and even lets Seyonne give him instructions in an emergency.
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Ascendance of a Bookworm takes place in the sort of setting where orphaned children are considered the property of whichever institution is caring for them, the institution is often keeping itself going by asking money for children taken away from it and the operation is treated like the child is being purchased on both sides. In addition to this, the odd commoner can find themself in a situation where their options are becoming a noble's slave or dying:
Freida is one of the aforementioned characters with the "slavery or death" choice. She's lucky enough to be born in a wealthy family, which allowed her to get a contract in which she will become an Impoverished Patrician's mistress upon reaching adulthood and be allowed to run her own store from her new home. The age gap between her and the man is on the low side for a deal that has to be made between a child and an adult. He also treats her as a proper guest when she visits his home.
The protagonist winds up as an orphanage's director, which means she has to handle any future purchases of orphans, some of whom are adults. She sees no reason to refuse the transaction if one of said adult orphans finds a person they actually want to serve and the person can afford to buy them.
After being Adopted into Royalty, the protagonist buys one of her attendants from her time as just the orphanage director and populates a new branch of her orphanage by buying orphans from the town in which it's built. She also helps a baby in the "slavery or death" situation by leaving a pre-signed ownership contract between herself and the baby with the latter's caretaker.
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Slavery is a thing in Shadow of the Conqueror, and—at least as it is known in Hamahra—is not depicted as evil. One enters slavery via one of two methods: voluntarily (exactly why anyone would choose to become a slave is not elaborated on), or as a criminal sentence. Voluntary slaves get a copper metal collar, whereas criminals sentenced to slavery get a steel one with the duration of their sentence and the date of their conviction etched into it. Daylen receives this at the end of then novel as a life sentence after finally being tried for his warcrimes.
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House-elves in the Harry Potter series have Happiness in Slavery as their hat; setting them free is probably the cruelest thing you can do to them, analogous to throwing them away. However, as explained in Harry Potter and the Deathly Hallows they still like to be treated humanely and will be reluctant to serve (and sometimes betray) a wizard who's mean to them. Thus some of the wiser and more kind-hearted wizards owning house elves will act like Sympathetic Slavers, such as Dumbledore does towards the Hogwarts kitchen elves (he's explicitly willing to pay Dobby, and in fact pay him considerably more than Dobby was willing to accept, suggesting that he'd probably be comfortable paying them instead, but they won't hear of it) and Harry towards Kreacher.
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Emperor (2020): Mostly averted, but Shields' first owner, Duvane Henderson, comes across as a flawed Upper-Class Twit, but one who is far more humane than his peers. He appreciates and listens to Shields' comments about the running of the plantation when Shields' new owner whips him for not acting subservient enough later in the movie, and Duvane' actions seem to go beyond Pragmatic Villainy. He respectfully tips his hat to Shields as he and his family leave their former home. He also lets Shields' son Tommy take books to read and listen to Duvane's children's nursery stories. Once Randolph wins Duvane's plantation in a card game, things rapidly go downhill for the slaves.
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Trail of Glory: During the timeskip between Rivers of War and The Arkansas War, Sam Houston sees fit to establish himself as a southern gentleman with political ambitions, and to avoid the proverbial kiss of death that overt abolitionist sympathies would be he must perforce be a slave owner. Therefore, he is in the habit of purchasing a personal servant (he wanders about too much to properly manage an actual plantation), manumit them and their families after the servant has picked up a perhaps vaguely unseemly set of useful-to-profitable skills (firearms, horse-riding, literacy, etc.), buying another manservant, and repeating the whole thing. He is a nationally famous war hero if an eccentric one, who is to tell him what he cannot do with his property?
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12 Years a Slave: Ford, at the very least, does reward his slaves for hard work and isn't needlessly cruel. Solomon in the book especially saw him as a decent person twisted by a corrupt society.
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Minotaur Hotel: While Asterion is officially a "servant", he's basically a slave in all but name. That being said, he's had a least a few masters that were mostly benevolent, even if was for reasons that had nothing to do with Asterion himself.
Joseph the Merciful refused to torture Asterion, though mostly out of his religious beliefs telling him so. Asterion looked back on him fondly.
Jean-Marie was not above punishing Asterion, yet he only did so if he truly believed Asterion deserved it. Otherwise, he was a splendid master, doing everything he could to fulfill the hotel's mission, and make it the best it could have been.
And of course you yourself in the Main route (and to a lesser extent the Lukewarm route). In the Main Route, Asterion even declares you to be the best master the hotel has seen due to you going out of your way to not hurt Asterion while still fulfilling the hotel's mission. At that point though, you don't even see Asterion as a servant, so it's essentially just a technicality.
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+Anima: Crystala is a slave trader who seeks to give the slaves she owns a fulfilling life. In Sailand, her slave caravan actually serves as a safe haven for +Anima, where free +Anima would otherwise be captured and probably enslaved to worse masters. She even used to own Senri in the past, and had taught him many things.
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The Confessions of Nat Turner: Played with, sometimes played straight, sometimes subverted. Samuel Turner is initially portrayed as about as sympathetic a slave owner as one might find in 1820s Virginia. He gives his slaves adequate food, clothing, and shelter, and forbids anyone to beat them. He takes on the education of little Nat and, after Nat learns to read, promises him his freedom. But Turner's lip service to the idea of helping blacks is shown to be insincere; when he runs into financial difficulties he sells off all his other slaves, while he simply forgets about his promise to Nat, leaving him in the care of Rev. Epps until Epps sells Nat to a different master. Nat also admits that his last owners, the Travises, treated him reasonably well, even as Nat planned their murder. Young Margaret Whitehead is the most straightforward example, a kindhearted and pure young woman who even goes so far as to tell Nat she thinks "darkies" should be free—but she does not actually own any slaves of her own. This trope is thoroughly averted elsewhere in the novel in cases of other slave owners, who are savagely cruel. One slave master gets drunk and forces two of his slaves to fight in public.
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TRON: As the Programs are, essentially, a Servant Race created by humans (who have no idea they are sentient), most of the human characters are this by pure accident. Needless to say, Disney does their best to downplay this.
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×××HOLiC: The protagonist, Kimihiro Watanuki, is plagued by visions of ghosts and monsters, and asks the witch Yuuko Ichihara to help him. In exchange for her help, he agrees to become her de facto slave: she does genuinely care for him, but also enjoys having fun at his expense.
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Mass Effect 2: Though the batarians are regarded very unsympathetically for considering it a cultural right to raid other planets for slaves, indentured servitude is legal (and heavily regulated) on the asari colony Ilium. In one optional interaction, Shepard can meet a quarian software developer who sold herself to an indenture agency to cover gambling debts; one solution is to arrange for her to be purchased, freed, and properly hired by a programming company rep (who then garnishes part of her wages to cover the purchase price).
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Silverfall: Stories of the Seven Sisters (a collection of Forgotten Realms short stories). The Harper named Dove goes to a slaver in Scornubel for information. When he realizes who she is, he asks her why she hasn't killed him (since Harpers kill slavers). She says that she has been keeping track of him over the years and knows that he is tender and kind toward some of his slaves, including freeing female slaves and arranging for them to meet men who would be good romantic matches for them.
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In The Roman Mysteries, Flavia treats her slave Nubia as a friend, rescuing her from her previously abusive master. Eventually, Nubia is even freed and continued living with Flavia as her true friend.
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Star Wars: The Old Republic:
Zig-Zagged with Darth Malgus. He became the owner of a Twi'lek slave woman named Eleena Daru. He used her as a Sex Slave and for other tasks, but became fond of her. The two even were a Battle Couple at the sacking of the Coruscant Jedi Temple and considered each other common-law husband and wife. Still, Malgus beat Elena when displeased (and since he's a Sith, he was often angry...), and Eleena had no legal status other than being the favored property of a high-ranking Sith. In the end, one of Malgus's rivals pointed out she could be used as a weakness against him, and he murdered her in her sickbed. Of course, he faced no repercussions; Sith are above any sort of law, and she was just a Twi'lek Sex Slave, after all.
Can be played straight with a Sith Warrior. Their first companion character is Vette, a Twi'lek woman who used to be a criminal. The Warrior can treat Vette as a little sister or (if playing male) a treasured concubine, but it still does not change that Vette is legally property, not a person.
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Schindler's List: Schindler starts out as a self-interested war profiteer, undisturbed by the fact that his laborers are unpaid prisoners, but gradually morphs into this until his only motivation for buying as many Jewish "slaves" as possible is to save their lives. In the end, he saves over 1,000, but is distraught that it wasn't more and breaks down before the survivors. He is the only Nazi Party member buried in Israel, and was awarded for saving so many, making it clear just how completely against the Nazis Schindler went.
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In The Familiar of Zero, an ordinary teenager Saito Hiraga becomes a familiar (and basically a slave) of a young magic student Louise. Louise acts in typical Tsundere fashion, often acting haughty and demanding to Saito, physically abusing him, and going from berating and yelling at him to kissing in the matter of seconds. She does mellow out to him over time though, and they eventually marry.
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Vinland Saga: Deconstructed thoroughly with the character of Ketil. He seems to be playing this straight at first, a fairly nice man who treats his slaves with respect and even promises Thorfinn and Einar their freedom once they finish preparing his new fields for harvest in a few years, but you soon see the problems as you get further into the farming arc. Ketil does not offer the same promise to his female slave Arnheid, and uses her as a Sex Slave to boot. After he suffers a Despair Event Horizon, he beats Arnheid nearly to death despite her being pregnant with his child, and still refuses to part with her after Leif offers to buy her. When all is said and done with the Farming Arc, Ketil is left grieving over Arnheid's death. Through all this we can see that while Ketil does not go out of his way to treat slaves badly, he still uses them for his own needs and is not above exploiting his status as his master to take out his frustrations on them or to make them suffer.
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The book The Eagle of the Ninth (and its film adaptation, The Eagle (2011)) deals with two boys, one a Roman officer, one a recently captured Briton slave, going on an extended quest in which the possibilities of murder, and escape come up, and their positions are reversed when they finally meet the Briton's tribe. But his compassionate and trusting treatment of his slave to that point is then rewarded.
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Wyvern Queen: Master Yezzen thinks he's this, that slavery is simply a facet of how the world works, and that his slaves are happy serving him. Edelgard disagrees. In reality, it's Downplayed, his slaves do want freedom, but they also don't think he deserves to die and they demand that Edelgard spare his life when she takes over Yunkai. To his credit, Yezzen genuinely does hope Edelgard can prove herself right in her assertions that Yunkai does not need slavery, and regrets that he can't do much to support her once she takes over because of his sickness. In the end, it's played straight enough for Yezzen to get a second chance at life, though the fact that he converts to Seirosism afterwards only manages to make the tension among the Black Eagles worse.
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Tales of the Five Hundred Kingdoms: In The Fairy Godmother, the titular fairy Elena punishes prince Alexander for his cruelty by transforming him into a donkey and taking him into her custody, where he is constantly made fun of and has to do a lot of work. Eventually he makes a Heel–Face Turn, after which she warms up to him, and eventually they become a romantic couple.
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Incarnation of Legends: Romulus describes the people he captured for use as labor in Rakia as vassals rather than slaves. He also swears to Bell that they will not be used as tools and will instead be treated as individuals who will one day become part of Roma, albeit they have no real say in the matter. This does little to assuage Bell's misgivings, and Romulus accepts that Bell doesn't agree with his viewpoint and doesn't begrudge him for it, instead wishing him well in his travels despite the sour note they part on.
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Aveline's father in Liberation has slaves as it was typical for anyone of status in 1700's New Orleans, but he is depicted as a very sympathetic character, friendly and humane to those who work for him. In fact, Aveline is his child with an African woman he owned, whom he then freed.
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Pokémon: This trope is discussed, where trainers occasionally question the ethics of having animals fight for them. This is complicated by the fact that most Pokemon are Blood Knights with superpowers and that the game encourages you to befriend them: the general impression is that it's much more a symbiotic relationship than master-slave.
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In The Bible, Potiphar, the Egyptian who takes Joseph as a slave, isn't as horrible as one might expect, and Joseph's Darkest Hour doesn't come until he's imprisoned over a False Rape Accusation from Potiphar's wife. The musical Joseph And The Amazing Technicolor Dream Coat portrays him as Affably Evil, while the animation Joseph: King of Dreams portrays him as explicitly sympathetic, reconciling with Joseph after the latter fulfills his destiny.
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In How Not to Summon a Demon Lord, Diablo technically owns his two female companions (Shera and Rem) as his slaves, due to an enslavement spell they used that had Gone Horribly Wrong. As a result, the girls were bound with enchanted Slave Collars around their necks that force them to obey Diablo's commands. However, Diablo always has their interests in mind and almost never uses his power over the girls, with the only instance he was forced to use it was to break Shera out of a Brainwashed and Crazy trance.
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In Game of Thrones:
Mereen is a city run by "the Masters" that Daenerys conquers and frees the slaves. As penance for the Masters crucifying over 162 children, she has an equal number of slavers crucified. Later episodes, however, show that some of the Masters were kind and spoke out against the acts, and some slaves found Happiness in Slavery because they were essentially members of a family.
There's a bit of a subversion early in the series. Daenerys marries Khal Drogo, and part of the deal for him to get her, would be that he would lead an invasion of Westeros. In preparation for this, Drogo leads numerous raids, which in Dothrakki fashion leads to multiple women being enslaved. Daenerys, appalled by the slavery, tries to play into this trope, preventing some women from being raped by claiming them as her slaves. This later bites her in the ass when she comes to trust one of the slaves to heal Khal Drogo, and the woman instead renders him catatonic. Daenerys expected the woman to be a loyal, helpful slave, grateful for being saved by her and well treated by her owner, when she failed to account for the fact that the entire reason the woman was enslaved to begin with is because of Daenerys' claim on Westeros.
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Hamilton: John Laurens is from a very wealthy slave-trading South Carolina plantation family. Despite this, he is a committed abolitionist and dreamed of raising a battalion of slaves whom he intended to free afterward. This just makes his untimely death in battle near the end of Act I even more tragic.
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American Girls: Felicity: Felicity Merriman's family has two servants, Marcus and Rose, and whilst the book does clearly imply the two being slaves, they are by and large treated well by their owners.
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Epic Rap Battles of History discusses Thomas Jefferson's historical reputation as this in his battle with Frederick Douglass; he openly acknowledges the evils of the institution while making rather weak, hypocritical excuses in his own defense when called out for participating in it, and while Douglass refuses to forgive him, he and the overall tone of the battle ultimately still acknowledge his genuinely positive accomplishments. Basically the whole battle is a big What the Hell, Hero? towards Jefferson without outright condemning him.
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How a Realist Hero Rebuilt the Kingdom:
Souma enslaves Castor and Carla Vargas following their defeat in the Elfrieden Civil War. Considering the alternative was beheading them both,note Besides the fact they only rebelled because they were Locked Out of the Loop on a Zero-Approval Gambit that Souma had arranged with Duke Carmine, their execution would be politically untenable because they're respectively the son-in-law and granddaughter of one of Souma's chief allies, and Carla is respectively the childhood friend and the cousin of two of his wives-to-be. nobody concerned really complains. He places Castor in the custody of his mother-in-law Duchess Excel Walter, while Carla is placed in the royal palace to serve as a Ninja Maid—with secret orders from Souma himself to kill him should he slide down the slippery slope into tyranny.
A young man named Ginger Camus inherits the slave business from his grandfather (who apparently was this trope as well) upon his death. At first, he intends to slowly sell off the slaves to good people (even making sure that those who are family stick together), and not only makes sure to treat all of them well, but also goes the extra mile by teaching them to read, write, and do arithmetic to give them more value than just sex slaves or manual labor. Despite initially suffering financial losses due to his reluctance to sell slaves to bad owners, Ginger hits the Karmic Jackpot when Souma's change in policy caused his educated slaves to become highly sought after as bureaucrats by the Idle Rich. Souma immediately recruits him as a subordinate in order to manage a training facility to prevent people from falling into slavery, with the goal of peacefully making slavery obsolete so that there are no significant objections when he eventually outlaws it.
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In the Detectives in Togas children's books, the main characters are preteen sons of Ancient Roman senators with household slaves, whom they're generally pleasant towards. They also buy their teacher a slave as a birthday present in the second book, but end up working with him to solve a mystery and ultimately grant him freedom in thanks.
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Beloved: Mr. and Mrs. Garner seem like good slaveowners at first. Mr. Garner believes in treating his slaves like men: "'Now at Sweet Home, my niggers is men every one of em. Bought em thataway, raised em thataway. Men every one.'" The slaves at Sweet Home get to act more like employees than slaves, encouraged to correct Mr. Garner, or even defy him and do what's needed without asking for permission. Paul D later starts to question Mr. Garner's intentions and asks himself whether there could be such a thing as a good slave owner. Halle never fully trust Mr. Garner, either. He points out to Sethe that Mr. Garner let him buy out his mother Baby Suggs's time at Sweet Home, but in return, Mr. Garner got him, Sethe, and their three children. Wouldn't a truly benevolent slaveowner just emancipate his slaves? Once Mr. Garner dies and Mrs. Garner becomes sick, the slaves are left to schoolteacher's horrible treatment.
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Disney's Aladdin:
Prince Ali, Aladdin's prince persona, is advertised as a benevolent master. The slaves that accompany Ali/Aladdin during his Big Entrance are actually conjured by the Genie.
Aladdin himself becomes a slave owner once he gets the lamp, with the Genie as his slave. He promises that he'll free the Genie with his last wish, but not before he fulfills his first two wishes.
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League of Legends: Azir was the ruler of an empire that made extensive use of slaves, and he owned many slaves himself, including Xerath, his best friend since childhood. He was against slavery, but even though he was emperor, he could not overturn slavery so easily—Shurima's noble houses had relied on slavery for wealth and power for millennia, and openly opposing slavery would likely get him assassinated. So he kept his plans to end slavery a secret, and never told Xerath about any of it, believing Xerath wasn't in a hurry to be freed. Xerath eventually came to resent his best friend for seemingly not lifting a finger to free him, and his plans to betray Azir eventually destroyed Shurima just after Azir made his move and declared all of Shurima's slaves free.
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The Chronicles of Narnia: In The Voyage of the Dawn Treader, the magician Coriakin governs an island inhabited by foolish dwarf-like creatures known as the Duffers. They see him as their oppressor, but in reality, he has to force them to work in the garden using tricks and magical spells because they are otherwise Too Dumb to Live (for instance, they tried to plant boiled potatoes, so they would not have to boil them later), and would not survive without his oversight.
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In No Game No Life, Feel Nirvalen's elven family owns Kurami Zierh's Imanity family, due to the Zierhs losing to the Nirvalens generations ago and being Made a Slave as a result. Feel, however, treats Kurami like a friend or even a daughter, and is determined to outlaw slavery in Elven Gard despite the fact that doing so is tantamount to treason.
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The Count of Monte Cristo: The Count claims not to be one, saying he has right of life and death over his slaves, though his actual slaves don't seem to consider him a bad master (Ali is too grateful for the count saving his life, Haydee considers herself his slave to the point of refusing freedom and wishes he'd love her as she loves him). As slavery is outlawed in France, it only adds to his mysterious Oriental schtick (everyone who works for him has their own theory as to where he's from, but they all believe he's from the Eastern Mediterranean).
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Sir Topham Hatt, aka The Fat Controller, of The Railway Series and its Animated Adaptation Thomas & Friends, can be considered a family-friendly variant of such. Part of it comes from the fact that the engines, being sentient but limited objects, require managing and are built to enjoy their work, however, the Fat Controller represents a stern but caring father figure in his railway, a case that, in the books especially, is ever decreasing due to steam being abolished and most other railways having their engines coldly disposed of and scrapped. Other limelight examples such as the Thin Controller in both media also usually count.
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The Alchemist Who Survived Now Dreams of a Quiet City Life: The main character, Mariela, awakened from a 200-year-long sleep and has to adjust to living in a world that she's unfamiliar with. She makes it to the nearest town with the help of a caravan that happened to be transporting slaves. When she sees a severely injured slave about to be subjected to a Fate Worse than Death, she decides to buy him on impulse to save him. Although the slave, Siegmund, has endured a massive Break the Cutie process before meeting Mariela, thereby obeying all her commands, she treats him with kindness and compassion, from making food for him to making special healing potions to heal his many injuries, some of which he had sustained years ago and never got treatment for them. Mariela personally hates the idea of slavery, but knows there's not much she can do about it, and is at least happy to be able to help Siegmund and allow him to be his own person. Needless to say, Siegmund blossoms under her care and by the end of the first novel, he's much better off than he used to be, promising to stick by Mariela and protect her like a bodyguard, though she wants to see him as a friend.
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Marcus Didius Falco, the hero of a long sequence of books set in Ancient Rome, ends up fitting the trope, as do most of the other sympathetic characters in the books. It's unavoidable; they're living in Ancient Rome and not dead broke, so it would be very weird if they didn't own slaves. But they're drawn as likeable for modern readers, so they treat their slaves quite decently on general principles.
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Belisarius Series:
Belisarius once purchases a slave as a clerk and on another occasion enslaves captured POWs. On both occasions, this was a temporary state.
Prince Eon's Battle Butler and Stern Teacher in the same series was also a temporary slave who had volunteered and would be freed and rewarded lavishly when his job was done if Eon's fellow soldiers decided he had done his job well.
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Rimworld: Certain traders will buy or sell slaves. Buying a slave is essentially buying a new colonist since they aren't treated any differently from colonists who join you willingly. Selling anyone into slavery will give all of your non-psychopathic colonists a negative thought. There are Game Mods that allow you to keep slaves or force prisoners to work for your colony, but how humanely they're treated is up to the player.
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Aida not only becomes Amneris' personal handmaiden, the latter genuinely comes to regard her as a confidant and friend.
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Monstress: Mistress Ilsa. A slave dealer whose specialty is Arcanic children, she is pretty unquestionably a villain. However, she isn't terrible about it. She lies to the children about their fate at the Cumaea compound (though that might have been to keep them from struggling), she offers Maika her cigarette in a small act of simple kindness, and when Maika is unchained and led into the compound, she wishes her well and asks her to send her best to her daughter, who apparently she doubts she'll ever see again.
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Assassin's Creed:
Aveline's father in Liberation has slaves as it was typical for anyone of status in 1700's New Orleans, but he is depicted as a very sympathetic character, friendly and humane to those who work for him. In fact, Aveline is his child with an African woman he owned, whom he then freed.
Vitruvius, a Quest Giver from Origins is a Roman slave owner in Egypt responsible for the construction of one of the Romans' aqueducts. He sees his Egyptian slaves as his own people and does his best to protect them from the harassment of the Roman soldiers. In addition, from what we see of the construction site, the workers are healthy and well-treated, being allowed rests and frequent meals.
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The people who sold Theo Ngoni into slavery in the Mortal Engines series are implied to be this. Based on Theo's own descriptions of them, they didn't want to sell him, but he was a prisoner of war and keeping him near the front lines of the conflict was deemed too much of a risk, he was treated remarkably well while in their custody, and he bears them almost no ill will.
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Fire Emblem: Radiant Dawn: Hetzel bought and nursed Rafiel when he was sold from an auction. Unfortunately, this is his only redeeming quality, as his cowardice and passiveness allowed the corrupt Begnion senators to do as they please. None of the heroes sympathized with him as he still stands against them, and even Rafiel refused to speak to him.
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The title character of Uncle Tom's Cabin had three masters, and the second master was the most sympathetic of them all. Alas, all good things must come to an end, and after a series of tragic events, the deceased master's widow, broken from the tragedy, decides to sell off all of the family slaves, and then in comes that total arsehole named Simon Legree...
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Being Able to Edit Skills in Another World, I Gained OP Waifus: Souma Nagi gets summoned to another world along with the rest of his class, but rather than follow everyone else, he ticks off the king and is thrown out where is he left to fend for himself. Shortly after he keeps gaining slave girls through circumstances beyond his control, but he always treats them with respect and cares for them even though they would like nothing more than to submit to his will and bear his children.
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The following is a list of statements referring to the current page from other pages.

 Sympathetic Slave Owner
processingCategory2
A Slave to the Index
 Sympathetic Slave Owner
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Morality Tropes
 Sympathetic Slave Owner
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Undead Horse Trope
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