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I don't see it as rigth to say to people(of either species) you now have to live with elves getting paid and wearing clothes.
Well-- but it isn't about money or clothes. Admittedly, in practical terms, money often
is a major issue in dealing with slavery, because giving people cash is the simplest method of compensating them for their labour, and, once freed, a wealthy person has considerably more power than an impoverished one-- Chrysogonus may have been barred from holding public office, like any freedman in the Roman republic, but his wealth (and his association with the dictator) made him scary. But it's mostly about acknowledging that people-- whether they be human, elf, or any other sentient species-- have rights.
Look at Winky.
She didn't like being enslaved either. You could never get her to put it in those terms because she had been indoctrinated with the idea that 'freedom' meant 'dishonour,' but she didn't. The idea of liberation as a form of punishment makes the form of slavery inflicted on house elves particularly obnoxious because it absolves wizards of
any duty to their ex-servants. There is nothing like the patron/client relationship that, at least theoretically, meant that a former master had to take an interest in the well being of his freedmen.
What Winky
wanted was her job and her home. She had the illusion of freedom. With Mrs Crouch dead, Barty Junior reduced to a kind of permanent childhood by the Imperius Curse and Crouch himself obsessed with work, Winky was mistress of the house. She mothered Barty and could and did bully Crouch into giving his son treats. Though Hermione was first horrified that Winky had been stuck in the Top Box, though she was terrified of heights, that is in fact
exactly where Winky wanted to be; she spent months persuading Crouch to let her take Barty Junior to the Quidditch World Cup.
But because she was a slave, Crouch could take those things from her on a whim. However happy her life may have been, it could be torn apart in an instant. She couldn't appeal her dismissal, or plant her hands on her hips and point out that
Crouch was supposed to be managing the Imperius Curse and it was hardly
her fault if he wasn't strong enough to subdue his son forever. Crouch had no duty at all to treat her fairly, or to help her find a new position once he had sacked her. Her inability to get her job back destroyed her, drove her to depression and alcoholism. It didn't matter that she had a place at Hogwarts, where she would be well treated; that wasn't what she wanted, and the things she
did want had been taken away.
If she had been free, Winky could not have been dismissed so brutally, and certainly not without Crouch offering her something in return. Perhaps Dobby
was exceptional in wanting a salary and as many socks as he could get his hands on. Perhaps house elves, as a species, have no particular interest in money and clothes-- as goblins have their own ideas about property and inheritance-- but Dobby was
not exceptional in wanting some control over his life. Winky's misery and Kreacher's initial horror at having been bequeathed to Harry Potter make
that clear.
In Order of the Phoenix Kreacher primarily represented an aspect of Sirius' past. He was simplified, as Mrs Black was simplified, in order to make number twelve Grimmauld Place better represent 'bad memories,' and thus a kind of second Azkaban. Though there are hints of a family resemblance between Sirius and his mother, the strongest image with which one is left is the screaming, dogmatic portrait, interesed in nothing more than causing her firstborn pain. Kreacher, too was 'what he had been made by wizards;' what
he thought was unimportant. What mattered was that he kept up that horrible litany of bigotry, the things that his mistress thought.
The kind of freedom that Sirius might have offered Kreacher at that point would likely have destroyed him. At sixteen, Sirius ran away, removing himself from a poisonous environment. Since he couldn't run away again, he did to the entire house what he first did to his bedroom-- stripped away all references to his family and filled it with his things, his people. Kreacher was just another nasty thing that his parents had owned-- and Kreacher himself didn't help matters by acting like a broken record-- and he could only have freed him in the same sense that he 'freed' so many of his other possessions: by throwing him out. Even had somebody convinced him that liberating Kreacher was the moral thing to do, I doubt he could have done so with much grace, any more than he and Snape could convincingly shake hands. Kreacher
might have survived by running off to Narcissa, but still, given his mental state and the length of time he had spent couped up in the house, it doesn't seem likely that he could have fared well.
Had Sirius lived long enough to achieve some kind of perspective and realise that the balance of power had shifted-- that Kreacher was
not just a relic of the oppression of his mother, but a person in his own right, who had suffered his own tragedies, it might ultimately have been possible for him to offer him a different kind of freedom; had Sirius known about the circumstances of Regulus' death, he might have thought better of both him
and Kreacher. They had common ground: long imprisonment, the sense of having failed a loved one. Sirius and Snape never overcame their differences, but Kreacher was not Snape. He kept a secret because he was ordered to keep it, not because he couldn't face it, and once the poison was let out he was able to move on, change his mind about things.
Hermione claimed that 'Kreacher doesn't think like that,' when trying to explain how Kreacher was capable of betraying the Order. It was patronising, but it wasn't entirely wrong. Kreacher wasn't incapable of looking at the bigger picture, thinking that Regulus had died destroying something that Voldemort wanted kept safe and that therefore helping those who fought against him might be the best way to honour him because he was an elf, or even exactly because he was a slave. But the circumstances of his life meant that he hadn't had much cause to expand his horizons; he was preoccupied enough with dealing with the aftermath of Regulus' death and what it meant to Mrs Black. Dobby achieved intellectual freedom long before he was literally free. No doubt the emotional distance from his masters helped. The Malfoys just 'let Dobby get on with it,' except for reminding him to punish himself. He always had difficulty speaking against the Malfoys, because the order to punish himself for disloyalty was so deeply ingrained, but he had no great difficulty in thinking ill of them. He wasn't as well integrated into the family as Winky or Kreacher so he was best positioned to think of himself primarily as an elf and only after that as attached to his family. He could make decisions in terms of the greater good, like: it will be better for all house elves if Harry Potter survives. Of course, once he met him, he also found that he wanted to protect Harry for his own sake, but that doesn't negate his original decision.
Kreacher spent time in Dobby's company once Harry inherited him. Granted, they argued, but that doesn't mean Kreacher was incapable of hearing what Dobby said, or of considering what he heard again in light of his new affection for Harry. His battle cry was 'fight for my master, defender of house-elves!' That's Dobby's influence leaking through, combined with his own experience of Harry's kindness.
There were three groups that showed up late in the Battle of Hogwarts: the parents, led by Slughorn, in order to show that Slytherins sometimes are good in a crisis, the centaurs and the house-elves. The latter two groups are polar opposites: the centaurs, so determined to maintain their autonomy that they would rather be called 'beasts' than 'beings' and inclined to murder one of their own kind for associating with wizards, and the house-elves, so steeped in slavery that they regard liberation as an insult. Hagrid called the centaurs to battle, because maybe they needed to be shamed a bit, to see that isolating themselves wasn't always the right thing to do. The house-elves were led by one of their own, by Kreacher, because they needed to learn to make decisions for themselves-- they had to come to fight evil on their own terms. Dobby was the natural choice for the role of leader, but he was dead, so Kreacher became his successor: the one who appreciated Harry for his civility, who had personal experience of the evil of Death Eaters, who could make the house-elves do something of their own accord, rather than at a wizard's bidding.
Of course elves ought to be freed. The three elves that we know by name suffered due to their condition-- no, four, there was Hokey too, of course-- though only Dobby, who was, after all, an extraordinary person, was able to be blunt about how unpleasant it was to be a house-elf. People ought to have rights; elves are clearly people, not clever magical objects, like talking mirrors. What they want once they
are free is their own business. Goblins want to collect all the artefacts made by their ancestors; maybe house-elves want to clean bathrooms in exchange for room and board. Whether the ritual of clothes is necessary in order to
give them freedom, I don't know. From a legal standpoint, one might think it would be simpler and better for the Ministry to be able to declare that house-elves were all freed; that they were people and could not be held against their will or abused. It would spare them the unpleasant associations the act of being given clothes, and it would make the act of freeing them separate from removing them from their homes. It wouldn't stop all abuses at once, of course-- the attitudes of both wizards and elves would have to change, and that kind of thing takes time-- but it would give those in situations like Dobby's a way out. But house-elves are magical beings, and there is magic that goes with actions; in voluntarily dying for somebody, in retrieving the sword of Gryffindor, in putting your name in the Goblet of Fire. It might be that it really is necessary to give an elf clothing to free him, and that there is therefore the complicated unpleasantness of explaining away the shame to deal with. If that is the case, I think Kreacher would be one of the most likely candidates to accept it first, and lead the way. His relationship with Harry was good enough to allow for explanations, and in any case, that was the way his character arc worked. He arrived as a pawn, clinging to the views of a dead woman and easily manipulated by Bellatrix and Narcissa, and ended up as somebody capable of rallying his people and leading them into battle.