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A follow up of this related question: Why did the Ministry order a Dementor’s kiss for Barty Crouch Jr. without any trial?
If all the Dementors are loyal to Voldemort and Barty Crouch Junior is a Death Eater who Voldemort trusts, why did a Dementor torture Barty Crouch Junior?
When a Dementor sucked the soul out of Barty Crouch Jr., that was before the Dementors joined the Dark Lord. They only joined him after his return. When he returned to a body, he said the Dementors ‘will join’ him and the Death Eaters, indicating they hadn’t already joined them before.
“The Dementors will join us … they are our natural allies … we will recall the banished giants … I shall have all my devoted servants returned to me, and an army of creatures whom all fear …”
- Harry Potter and the Goblet of Fire, Chapter 33 (The Death Eaters)
As Harry figured out, they can be considered to have “officially joined” him when they let ten Death Eaters escape and didn’t attempt to find or recapture the escaped Death Eaters.
“It’s funny, isn’t it,’ said Cho in a low voice, gazing up at the pictures of the Death Eaters, ‘remember when that Sirius Black escaped, and there were Dementors all over Hogsmeade looking for him? And now ten Death Eaters are on the loose and there are no Dementors anywhere …’
‘Yeah,’ said Harry, tearing his eyes away from Bellatrix Lestrange’s face to glance up and down the High Street. ‘Yeah, that is weird.’
He wasn’t sorry that there were no Dementors nearby, but now he came to think of it, their absence was highly significant. They had not only let the Death Eaters escape, they weren’t bothering to look for them … it looked as though they really were outside Ministry control now.”
- Harry Potter and the Order of the Phoenix, Chapter 25 (The Beetle at Bay)
The Dementors only join the Dark Lord much later, so at that time, they’d have no reason to spare one of his followers.
Though they may “ally” themselves with others, Dementors have no true loyalty. They aren’t reluctant to feed on ‘evil’ or ‘dark’ people in general. They’re equally willing to feed off of Death Eaters as they are anyone else - when Barty Crouch Jr. is on trial for the torture of the Longbottoms, it’s clear they affect him.
“But the boy was trying to fight the Dementors off, even though Harry could see their cold, draining power starting to affect him. The crowd were jeering, some of them on their feet, as the woman swept out of the dungeon, and the boy continued to struggle.
‘I’m your son!’ he screamed up at Crouch. ‘I’m your son!”
- Harry Potter and the Goblet of Fire, Chapter 30 (The Pensieve)
Dementors feed equally off of the innocent and guilty people in Azkaban. Hagrid was innocent, but they still didn’t want to release him from Azkaban and lose a victim.
“Mind, the Dementors weren’t keen on lettin’ me go.’
‘But you were innocent!’ said Hermione. Hagrid snorted.
‘Think that matters to them? They don’ care. Long as they’ve got a couple o’ hundred humans stuck there with ’em, so they can leech all the happiness out of ’em, they don’ give a damn who’s guilty an’ who’s not.”
- Harry Potter and the Prisoner of Azkaban, Chapter 11 (The Firebolt)
Though the Dark Lord says the Dementors are their natural allies, this doesn’t mean that they’re truly loyal to him or won’t feed on Death Eaters - it only means that they’d be willing to join him because he’d supply them with more victims than they could either get from working with the Ministry remaining on their own.
“The rest of us sleep less soundly in our beds, Cornelius, knowing that you have put Lord Voldemort’s most dangerous supporters in the care of creatures who will join him the instant he asks them!’ said Dumbledore. ‘They will not remain loyal to you, Fudge! Voldemort can offer them much more scope for their powers and their pleasures than you can! With the Dementors behind him, and his old supporters returned to him, you will be hard pressed to stop him regaining the sort of power he had thirteen years ago!”
- Harry Potter and the Goblet of Fire, Chapter 36 (The Parting of the Ways)
Therefore, there’s nothing specific about Death Eaters that make Dementors unwilling to feed on them. The Dark Lord only offered them a more convenient way to get larger numbers of victims.
At that point in the story Voldemort had just been reborn a couple of hours earlier. For the previous 13 years he had not been around, and the dementors had been working for the Ministry. In the graveyard Voldemort claimed that the dementors would join them, but that is a future reference:
The dementors will join us... they are our natural allies...
Similarly, Dumbledore argued that the dementors would join Voldemort, again speaking of the future:
"Voldemort has returned," Dumbledore repeated. "If you accept that fact straightaway. Fudge, and take the necessary measures, we may still be able to save the situation. The first and most essential step is to remove Azkaban from the control of the dementors -"
"Preposterous!" shouted Fudge again. "Remove the dementors? I'd be kicked out of office for suggesting it! Half of us only feel safe in our beds at night because we know the dementors are standing guard at Azkaban!"
"The rest of us sleep less soundly in our beds, Cornelius, knowing that you have put Lord Voldemort's most dangerous supporters in the care of creatures who will join him the instant he asks them!" said Dumbledore. "They will not remain loyal to you, Fudge! Voldemort can offer them much more scope for their powers and their pleasures than you can! With the dementors behind him, and his old supporters returned to him, you will be hard-pressed to stop him regaining the sort of power he had thirteen years ago!"
When Harry gets attacked by dementors that summer, he wonders whether the dementors had already left the Ministry's control, once again implying that at the time of the attack on Crouch Jr. the dementors had not yet left the Ministry's control:
But at these words of Uncle Vernon’s, Harry’s exhausted brain ground back into action. Why had the dementors come to Little Whinging? How could it be coincidence that they had arrived in the alleyway where Harry was? Had they been sent? Had the Ministry of Magic lost control of the dementors, had they deserted Azkaban and joined Voldemort, as Dumbledore had predicted they would?
Even after that, at Harry's hearing, Fudge still maintained that the dementors were under Ministry control rather than Voldemort's:
“It means that I think they were ordered there,” said Dumbledore.
“I think we might have a record of it if someone had ordered a pair of dementors to go strolling through Little Whinging!” barked Fudge.
“Not if the dementors are taking orders from someone other than the Ministry of Magic these days,” said Dumbledore calmly. “I have already given you my views on this matter, Cornelius.”
“Yes, you have,” said Fudge forcefully, “and I have no reason to believe that your views are anything other than bilge, Dumbledore. The dementors remain in place in Azkaban and are doing everything we ask them to.”
“There are no dementors outside Ministry control!” snapped Fudge, who had turned brick red.
And Dumbledore's evidence to the contrary was that dementors had been ordered to Harry's neighborhood, but that evidence was undermined when we found out that it was actually Umbridge who ordered the dementors to attack Harry:
“What Cornelius doesn’t know won’t hurt him,” said Umbridge, who was now panting slightly as she pointed her wand at different parts of Harry’s body in turn, apparently trying to decide what would hurt the most. “He never knew I ordered dementors after Potter last summer, but he was delighted to be given the chance to expel him, all the same...”
In short, the dementors were not loyal to Voldemort at the time that Crouch got his soul sucked out.
Additionally, even when the dementors are technically on a specific side, they don't really care who they harm. Note Dumbledore's words of caution when the dementors were stationed at Hogwarts:
"It is not in the nature of a dementor to understand pleading or excuses. I therefore warn each and every one of you to give them no reason to harm you. I look to the prefects, and our new Head Boy and Girl, to make sure that no student runs afoul of the dementors," he said.
No matter how loyal a Death Eater was, for Voldemort, they were all disposable. He never had a second thought when he needed to sacrifice, or punish any of his followers. The loyalty to him was based on fear, not respect. Also, he trusted no one. He needed servants, not allies or friends.
So even if the Dementor was acting on Voldemort orders (it was not), kissing Barty Crouch Jr. was useful to Voldemort in several ways:
However, the Dementor was acting on its own accord (possibly with gross negligence on behalf of the Ministry). But the result still had its advantages for Voldemort.
As for the Dementors' motivation: they have no loyalty, but hunger for souls. So they do not care whose soul they suck, provided they have an opportunity. It appears that the Dementors cannot really be controlled, because they can easily be manipulated by anyone who offers them more souls. This is the reason why, after Voldemort's ultimate defeat, the Dementors were removed from Azkaban and replaced by human guards.
Because (a) while the Dementors were technically working for the Ministry, their true loyalties are towards Voldemort (as Dumbledore warned Fudge), (b) they have a fairly good idea of where their true master's interests lie, and (c) at that point Crouch was a liability to Voldemort.
This also explains why they attacked Harry without provocation on multiple occasions; they recognized him as an enemy of their master. (I admit that this point is not touched on in the books, but it makes a whole lot more sense than anything else offered.)
