#Alastor's deal theory

[lyrarizi]

Alastor theory time:

I have had a theory about his soul deal for so long and i decided to finally share it

I think Alastor sold his soul when he was alive, dont come at me. It just makes much more sense to me than him selling his soul in hell. Imagine you just arrive in hell with an gigantic amounts of power, i wouldn't need to sell my soul for more power if i already got so much.

Now how to explain this is that lilith OR roo (i really like the roo theory) came to him when he was alive to kinda set him up as a puppet for when he would arrive in hell. He is a psychopathic serial killer, who wouldn't want to have him on a leash to do your bidding in hell.

But it makes much more sense cause when he was alive he would have no idea what a soul contract would mean, or he has suspicions that its weird but he would agree much faster. Definitely when roo or lilith would say that it could help him killing people who were like his father. He also canonnically is a mama's boy so roo or lilith could use that too.

But that is the part where he sold his soul, now what would happen in hell and his dissapearence

So when he came into hell he realized he was on a leash. We got 2 different routes that replies to the person, roo or lilith

Lilith:

- the killing spree of Alastor of overlords is not a command its just him wanting to kill them and show his power

- lilith wouldnt order him around much in the time when he arrived in hell and his dissapearence i think.

- when he dissapeared maybe she just locked him up for a time-out or he could have brought him to heaven, maybe to see his mother but that's a bit long stretched.

- after he came back he recieved an order to look after her daughter in the hotel or he went down there without an order to get close to the Princess of hell to free himself from his leash

But we also got roo who i think could be eve or her spirit became roo and Eve is sorta trapped in roo

So imagine this alright? You are the cause for sin to get a physical form or exist and you dont get to rule hell but you are banished while the ones who baited you into sin can happily rule hell and are the most powerfull beings there. I would be pretty pissed and angry.

Here's where Alastor comes into the story.

Roo:

- so she got his soul when he was alive and gave him some extra powers in hell (or all but that makes him really weak and kills his hype and kinda destorys his character, that he actually is a weak guy who recieved all his powers)

- here his killing spree on overlords would be a training for him to eventually kidnap the Queen of hell for roo

- could be that that was earlier in time and she disgueses herself as lilith to destroy the marriage between her and lucifer or lilith destroyed the relationship herself and got kidnapped which follows to her 7 year dissapearence

- so when Alastor kidnapped lilith he would no longer be of use and be put in time out (what really would make it tragic is what i read in a fic is that he would be locked up in a black void with nothing except himself for 7 years and i kinda love it)

- roo got notice of a hotel by the Princess of hell and that was her next target, the daughter of Lucifer and lilith, so she sent Alastor to the hotel to befriend charlie so she could use it later in her revenge

And now we are at the end of the series but some small things are (explained) further in this post:

- His rivalry with lucifer: he just hates him because of lilith

- the eyes following him would refer to roo watching him

- lilith on the beach could be eve just enjoying a vacation while her puppet is doing all the work

- also in ep5 it was eve's hair, not lilith she never had her hair like that

- my personal theory for alastor's smile is thats its stitched to prevent him from talking about his deal, sure be can talk that he made a deal otherwise Husk couldn't know but he cant say anything about what was in the contract and with who

I know the lilith theory is really popular but it just seems so obvious, too obvious and why would lilith even want alastor's soul i cant think of a reason for it

Anyways thanks for reading my theory ❤️

[evilsliceofbread]

Alastor made the deal to go to heaven with Lilith, to see his mom. Fight me. Why else would he sacrifice power and status, the 2 things he values most, to make a deal?

i also believe one of the conditions of his deal is he cant acquire anymore souls. What if it wasn't an actual condition, but his mom tryna keep him on the straight and narrow, and he doesnt wanna disappoint her anymore than ending up in hell already has?

the 7 year thing could be a red herring, and if it is, i think he made a deal with Eve. cause she hasn't been mentioned since the opening, and that'd be a good way to bring her into the story.

[wyxxiee]

Whatever shit of a deal he got himself into surely as fuck looks terrifying and traumatizing because are you telling me that SOMEONE stitched his smile on? OR he’s some sort of Voodoo Doll for someone to play on or control? 😧

[thefirstpaleontologist]

Anatomy of Alastors demonic forms

[savvydabbydoo]

HAZBIN HOTEL THEORY

What if Lilith made a deal with Adam to stop her uprising antics if she could go to heaven but before she went she got Alastor to make a deal that’d she’d leave hell, leaving a leaders spot open in her vacancy if he watched out for Charlie but he was tricked a little bit because Lilith put in the contract that he couldn’t use his powers to do anything that would over take leadership in hell or take Charlie’s soul. That’s why he couldn’t defeat Adam. And then he made the deal with Charlie and unable to take her soul to gain power over hell, he took a favor and what if that favor is to be put in charge in some way or to have the last say in any rulings she has in hell. He could even use the favor to get Charlie to marry him to get a higher position or use the pending nuptials to get Lilith to change the deal back in his favor.

[lolomidi]

Personally I don't want Alastor's power to be (at least solely) a result of his deal. It feels like a pretty obvious and almost cheap twist.

I think it would much more unexpected and crueler if he truly was a talented up-and-comer who made a name for himself, who was so close to attaining freedom and control over his life as an Overlord of Hell, only to be brought under someone's boot anyway due to circumstances outside of his control. Of course he'd be all about "taking control of his fate" after that.

[lacrimosathedark]

There's something that's bothering me about Alastor

I noticed something about Alastor's magic.

So Alastor's magic has either a red or green color at any given time.

Usually, it's green.

But, occasionally, it is red.

It's always red in flashbacks, and the two other times it appears red, Alastor is being intentionally threatening. It also may correlate to his shadow being active.

My concern with the green comes, partially, from this.

The bright green of his magic is the same as those stitching his mouth and arm. (Also now I'm worried his arm was ripped off at some point)

This could entirely be a stylistic choice, but if his magic only started being mainly green recently, maybe it has something to do with his deal.

Alastor's mouth being sewn shut and could mean he can't talk about his deal, or otherwise relate to being forced to smile.

I also think this because the spooky ghosty motif is also green, and might be representative of souls, in regards to Alastor at least, considering this:

and that Husk's leash is green too.

He also repeatedly rejects offers of collecting souls.

Rosie: Ya know, Alastor. I got a primo connect on a guy with about eight blocks of territory and not enough goons to run it. Prime pickins for a deal to be made, my friend. Alastor: Appreciate the offer, but we're here on business of another kind.

Gaining souls is how Sinners get stronger it seems. And we know he's not opposed to collecting souls as he already owns Husk and Niffty. So part of his deal could stipulate that he can't collect more souls for one reason or another.

What had me thinking, and what really worries me, is this.

The shield he makes in The Show Must Go On sticks out to me. Because the base of it is shadows, and there's that eye motif that is likely indicative of Roo. All of that is black outlined in red. But the veves are all outlined green, and there's this green mist near the base of the dome. Why are the symbols green but the eyes and other crack-like shadows aren't?

I think it might be possible that Alastor had a deal of some sort with Roo almost as soon as he got to Hell. But more recently, he has a new deal, one that limits him in some way, and likely one that forced him to the Hotel if Roo herself didn't order him to. And it's likely got something to do with Lilith, given their absences of the past seven years coinciding and then Alastor returning and going straight to Lilith's daughter.

Whatever this deal is, it limits his abilities. His figurative wings are clipped.

But this raises more questions for me. If he made some sort of deal with Roo or another entity for power, but he still owned his soul, what did he trade in the first place?

If he had so much power already, what would he have to gain from a deal that limits his strength and growth so much, especially at the cost of his own freedom? His own soul?

Who is this new contract with? Roo? Lilith? Eve? And why?

That also leads me to question, are he and Lilith allies or enemies?

Can your soul be owned between multiple parties if they make a deal with each other? Like, if Roo owned his soul and made a deal with Lilith to effectively share ownership, would that work? And what would that mean for them?

And, quite frankly, why Alastor? Was it convenience? Was it his connection to Roo?

This is in conjunction with something I noticed about those eyes that are all over Pride.

They don't appear naturally in any other Rings. (<- explanation under the cut now) And the motif only happens in two places.

There's Loo Loo Land in the Greed Ring.

Which, I'll remind you, is apparently a knock-off of a theme park Lucifer made, Lucifer's domain being Pride where these eyes are naturally occurring. Meaning the eye motif is probably just more mimicry. Especially since they aren't even red.

And then there's one room in Millie's family's house in Wrath.

It's obviously just a design, since none of them move and they look pretty flat, but that stylistic motif is present. The wide red eyes and black shadow tendrils.

And it reminded me of something.

Martha: Satan! We return your FILTHY creatures back to the pits of Hell! May the Root of Evil remain honored as we continue thy work!

If you look around during these scenes, you see a lot of eye imagery, both carved into the pole and scattered about the trees. And then on the top of the pole is Roo's emblem.

So, like, there's some kind of human cult around the Root of All Evil. Enough that the emblem is known.

Martha specifies Satan, who is the Sin of Wrath, where Imps originate. Wrath is the only place there's imagery outside of Pride and Pride-adjacent areas (Loo Loo Land being a knock-off would be just replicating)

So, like...does Wrath or Satan have some kind of connection to Roo??? I mean, Lucifer and Satan are often mushed into one character but are separate here, so maybe it's just human error? Or maybe Roo has some kind of connection with Satan but her influence doesn't extend beyond Pride? I saw somewhere that Imps tend to treat Satan like a god (and they say shit like "oh my Satan" instead of "oh my god") but do they also worship Roo maybe? Or does Satan somehow serve her?

And one of the few places in Pride free of Roo's eyes (to my knowledge at least) is Cannibal Town.

Where everyone's eyes are black voids.

Idk I'm tired and Alastor's whole deal has my head spinning in circles if I'm honest. And I needed to get it out somewhere.

EDIT WITH MINOR THE FULL MOON SPOILERS BECAUSE FUCK ME

I STAND GODDAMN CORRECTED ROO IS ACTIVE IN THE FUCKING LUST RING

I COULDN'T WAIT LIKE TWO FUCKING DAYS GOD FUCKING DAMMIT

WHEN THE FUCK DID THOSE EYES GET THERE?!

Did the DHORKs testing their portal give her an in to other Rings? cuz it also looked like she was fucking them up.

Which, btw, fucking YIKES

[inuhalfdemon]

Alastor and Niffty Fanfiction Headcannon

[I plan to write this into an actual fully-fleshed one-shot at some point…]

Alastor finding Niffty and bringing her back with him to Hell.

In Life:

Niffty was a “mail-order” house bride; brought bought from her family in Japan

She genuinely enjoyed cleaning, cooking and took great care in all of her wifely duties

Her husband was “a man of science”; his research (his findings, pointless at best) took priority over anything else and he demanded nothing but obedience and subservience from the women in his life

Niffty had a natural attraction for men so when her husband recognized that she was really and truly attracted to him and enjoyed sexually pleasing him; he immediately had her institutionalized into the local mental health hospital asylum for the insane (under the care of and study of a valuable colleague of his…) where she was lobotomized – not once, not twice, but three fucking separate times.

Even after the procedures were over;  and despite living the rest of her days in constant terror within the insane asylum itself, Niffty never garnered an ill thought toward her husband – always naturally supposing he had her best interests in mind.

Alastor is a selected participant in Hell’s regular reaping of souls event and for 10 years he has free access to and from earth

 Alastor came to the insane asylum – not for Niffty – but for a man that had feigned insanity in a poor attempt of preventing the radio demon coming and collecting his wretched soul following the completion of a deal that he had made.

The asylum was poorly regulated; patients were often left unattended and sexual and physical abuse among the population was rampant.

Niffty was a victim of such abuse by the man whose soul Alastor came to claim

When Alastor found the man within the asylum, catching him in the commitment of unspeakable and horrendous acts to the young woman…it turned into a rather bloody business, indeed.

Alastor finds NIffty’s records within the asylum and is appalled by what he finds

Mentally holding on by a thread and nothing but grateful to “the bad boy” that came to her that night as her own personal dark angel; Niffty readily gave him her soul.

Alastor took it from her; not to use but to protect from any further nefarious insult by anyone else who might seek to claim it

 Niffty doesn’t just give him her soul; she forfeits her life and follows him, going with him, to Hell.

In Death:

When Niffty first came to Hell she was incredibly erratic (yes, even more so than she is now)

She continuously darted all over the place and was entirely obsessed with bugs (yes, even more so than she is now)

She wouldn’t verbalize much; and when she did it was a continual string of variations to one word or complete nonsensical blabber

NIffty’s behavior drew open curiosity, agitation or concern from others residing in Hell but never Alastor

Alastor let her be and never once minded or objected to her constant and complete adoration of him

Alastor calmly allows her to frantically climb and clamber all over him – something he would never tolerate from any other being in Hell

Alastor takes pangs to set aside quieter moments with Niffty; times in which he encourages her to draw or write out her thoughts and whatever emotions she might be feeling

Her drawings are a series of indecipherable scribbles; usually black rings she draws going round-and-round in a chaotic fashion until the paper tears and Alastor gently has to persuade her from gouging the rings further into whatever surface they were utilizing

Her writings are what really start to develop and this is where her passion for creating fanfictions truly begins to blossom

Alastor doesn’t quite get it, but he’s happy to see that she’s found her own outlet and encourages her work

Niffty never knows this, but Alastor makes a point of finding her husband while he is still allowed to visit earth. He easily forms a deal with the rather foolish and short-sighted man; upon completion of the agreement he immediately rips the fucker’s soul apart – never bothering to find a use for it or add it to his collection of broadcasts.

Slowly; Niffty’s verbalizations and interactions with others develop and take form

Alastor enjoys watching her come into her own; seeing her develop relationships with others apart from him and finding a new and brighter confidence in herself

He is incredibly proud of her when he hears what she does to Adam; he also finds a great poetic justice in it: that she got to really and truly stick it to the first and original man; the original dick

Alastor keeps her soul…allowing it to mold and morph from something that was once less than tattered shreds – slowly becoming something beautiful and whole: until the day he can return it to her, knowing that she is ready to take it back.

[freogo]

thought of this song as soon as I saw episode 7

brings me back to those gravity falls animatics 😭😭

designs are based on @cholvoq 's designs !! wanted so bad to give Charlie the cool snake hair but after 50 frames I think I'd lose my sanity

[minzart]

I knew Alastor was gonna grow to be the dad figure, it's a given with mentors... but... HAVING A DUET WITH THE BIOLOGICAL DEPRESSED FATHER THAT ACTUALY WANTS TO RECONECT/CONECT AS A CUSTODY BATTLE WAS NOT ON THE BINGO LIST HOLD ON-

[baffledapple]

i've been pretty convinced already that alastor is INCAPABLE of not smiling but the finale has really cinched that in holy shit

my man can't even frown his shadow has to do it for him

even when he's losing his shit cause he almost fucking died he STILL couldnt frown

[syncrovoid-presents]

Alastor's Deal (Thoughts, Theories, and some Predictions)

This won't answer the who, but aims to dig into the why, and plausibly narrow down the terms of the deal. Long post ahead!

Evidence

First off, the finale was incredible! But what Alastor's song showed was that his ""death"" against Adam wasn't entirely a surprise, but rather planned. Alastor's song revealed that he was looking for a loop in the contract, a way to slip past the deal without having to directly break it. He already made a deal with Charlie for a favour, but that might have been a safety net of sorts, something to guarantee himself a fighting chance if his "dying for the hotel" plan failed.

His surprise was at how fast it happened, not that he nearly died. Alastor craves control, he wears his smile for control, he makes deals for control, his magic highly influenced by controlling others too. His Modus Operandi is control, and he faced the battle it started with him being in control. He was outwitting Adam, he was faster, sneakier, even kept his hands behind his back while dodging just to show how little effort it took. But Adam's weapon sending an angelic beam of power? That wasn't in his plan, that wasn't in his control.

Control is something Alastor seeks over everything, which is why the deal is so brutal for him. The deal takes control from him, and his constant smiling and jokes and contained urges for violence is him trying to have some sort of freedom. It's highly implied that, unless it's for the hotel, he hasn't used his magic for his own reasons. He hasn't eaten or killed anyone unless it is for the hotel, and even that was implied to happen only during the Mimzy incident. He hasn't gotten to make any deals either, at least no real deals, no deals for souls.

I'm far from the first one to say that his deal is forcing him to help the hotel, but it's only now that we see the true extent. Alastor's entire personality, goals, and being has been changed against his will. He is now a tool for the hotel, the sword and shield, the magical provider, bringing them whatever they need to succeed despite the odds. Without him, it would just be Charlie, Vaggie, and Angel Dust. Sir Pentious wouldn't have joined, repairs would've taken far longer, the staff would've been just Charlie and Vaggie, et cetera. Even his deals are just him trying to gain something out of helping the hotel.

Alastor is bound to the hotel and his powers are also bound to the hotel. He cannot be selfish, he cannot do anything unless it's for the hotel no matter how desperately he wants to do otherwise. And yet it seems like his powers are limited too.

Alastor has immense levels of powers, so much that he was taking down a large portion of the angel army single handedly. Had Adam not been there, it's not outlandish to claim that Alastor could have taken down the angel army by himself. This is why he was feared. This is why "no one crosses the radio demon". If these are his powers when their limited, imagine just how powerful he truly is?

The last evidence I'll state before moving on is that Alastor didn't return back to the hotel until it was rebuilt, yet still didn't use his magic to cause chaos.

To simplify, on his end the deal forces him to use his immense power for the benefit of the hotel. He cannot actively do anything to bring harm to it, and he cannot use his magic unless it's for the good of the hotel. And he cannot escape from the deal if the hotel is destroyed, so the deal isn't about the physical hotel, but rather the concept of it. As long as the hazbin hotel exists in the heart of those involved, Alastor is bound to help.

Why?

Now the why? I believe that, whoever he made the deal with him was, they want the hotel to succeed. Not only that, I believe that by forcing Alastor to stay there and help while limiting his capability for violence, they are also trying to rehabilitate Alastor.

Wherever Alastor was before the hotel opened, it was somewhere where he couldn't interact with anyone. He was forced to be gone, only until the hotel opened. If the theories of Alastor making a deal with Lilith is true, then Lilith's character is important to consider. From what we know she is powerful and worked to bring dekonkind together. And that she too disappeared 7 years ago.

It's confirmed that Alastor destroyed many of the worse evils that existed in hell, the only ancient overlords that remain are civil and take part of overlord meetings. They are controlled, contained. There's more structure, and the only truly out of control, dangerous demon to remain would have been Alastor. It's possible that Lilith realized that she could use him to "clean up hell", waiting her time until Alastor was the last remaining biggest threat. That was when she pounced, seven years ago to capture him in a deal. We don't know why he would accept such a limiting deal, but I'd wager that it could have been for his life (either she was threatening him, or he nearly died and made a deal for his life).

Now that the deal is made, Alastor can't bring mindless chaos. If anything he is doing the most to help demons be saved from the extermination either through redemption or protection (we also didn't see him prior to the last, so perhaps he's also bound to protect during the extermination too?).

All while Alastor is handling and ensuring the success of the largest and most helpful demon-centered support system, Lilith is on vacation. Almost like Alastor is acting in her role, a mimicry of a spiritual successor of sorts. He's helping rally the demons together, helping shape Charlie into a better leader, helping prove demons can be redeemed. All while Alastor is either witness, participant, or manager of the strategies used to redeem sinners. Alastor is only a few steps away from taking part of the redemption program himself.

If Alastor's deal was with Lilith, then she's getting everything she could want. All the uncontrollable evils/overlords destroyed, a muzzle on (one of the most) powerful sadistic demons, someone to help guide her daughter, help demons redeem themselves, protection for her citizens from being killed or further tortured, and she finally gets a vacation. She'd be getting everything she could want, with the bonus of possibly rehabilitating Alastor in the process.

It's no wonder Alastor is so desperate to break out of the deal, to find a backdoor in the contract. This goes against everything he stands for. The stories of him broadcasting screams? Of killing overloards and owning soul after soul after soul? That is the real him, and it isn't exaggerated. If Alastor wasn't chained, he'd have the power and strength to destroy large swaths of hell himself. If he decided to do his own extermination with angelic weapons? He could kill as many demons as the angels do and more, because he wouldn't be limited by a single day period.

If his deal is with someone else? We simply don't have enough information yet to name them then. Whoever it is, they would have to believe in demonkind's potential for improvement, and possibly fear what Alastor is able to do.

Predictions

The last thing I want to touch upon is how Alastor might be able to escape the deal. First is what he tried, which is "dying" for the hotel. Or, more precisely, for everyone involved in the hotel, it was as if he died, so why would they still depend on him?

Next would be for the hotel to be destroyed, and considering that we don't know if Alastor was briefly free while he recovered or if he was just hiding out somewhere new because he couldn't stay in the hotel because it didn't exist, this one is still iffy. If part of his deal is staying at the hotel to actively protect it, the he was temporarily freed from that condition. Yet once it was rebuilt Alastor returned, proving that the destruction of the hotel building wouldn't free him.

The next possible way could be the death of the hazbin hotel spirit. If Alastor (or outside forces) were able to destroy Charlie's hope for the hotel just like Lucifer's dreams were crushed, perhaps Alastor would be freed. Considering how the finale went, it would take a lot for this to happen.

My final idea, and the one I predict will happen, is that Alastor outfits the person he made the deal with. He doesn't find a true "out", but rather will manipulate them into giving his power back. And this? I believe that Alastor's deal with Charlie was made for this reason.

If indeed the deal was with Lilith, and part of the deal seems to be ensuring Charlie's dreams come true, then Charlie is a delightful way for Alastor to manipulate the situation. How? Who knows, but I think that this will be a large part of the conflict of season 2.

[jieloksworld]

PT 2 of "Alastor made a deal with Lwa" aka normal explanation

so the main thing about having a deal with Lwa is that they give a person the powers or whatever they want and in exchange the person gives them their soul and undertakes to supply them with food bc Lwa are hungry for blood

and that's what Alastor does!

he was given the powers and as we know he was a serial killer while alive (half confirmed, but a huge fanon fact) and continued this way in hell

also the deal with Lwa explains why the power shield Al made during the battle for the hotel couldn't be broken by angelic powers-

as we know, demons' power is vulnerable for angels' power and angels can't be hurt by it

according to Vodou religion, Lwa aren't demons - they're Deities

so that's why the exorcists were unable to pierce the shield with angelic weapons - because it was created by divine power essentially equal to theirs

another thing I noticed (not really a proof to anything, just an interesting detail) is that in Alastor's part of Finale he sings about how he wants to break the deal and "unclip" his wings to be free

and here we have his tentacles in his demon form situated right where wings are usually are

so here are my thoughts on Alastor's deal

:P

PT1 :

[power-up-girl]

GUYS!!

Ok ok listen, What if alastor's deal wasn't for him or power, but was for his mother??

Let me explain..

What if alastor's mom wasn't in heaven at first, so al made a deal with lily to put her in heaven, and so Lilith made a deal with Adam to let her and alastor's mom into heaven, in exchange of a favour from her to Adam

What do you think ??

[radiationhaz-ard]

I am usually a proponent of the theory that the making of Alastor’s deal is what made him disappear for seven years. But hear me out.

Alastor makes his deal pretty much immediately after he arrived in hell but NOT for more power. Imagine for a second that Alastor IS that powerful when he lands in hell. That’s not the problem. The problem is that Alastor lost one of the things he considers a key component of his sense of self when he arrived in hell: his voice. Because the character we perceive as Alastor isn’t him at all. The shadow is the real Alastor and what we see is actually a doll that he puppets around.

The reason all of his magic stems from the shadows? Well that’s just him. The little doll minions? Prototypes for Alastor’s puppet body. The stitches, the smile? Well you can’t sew a seamless doll nor can you change one’s face very easily.

So you have an Alastor new to hell and incredibly powerful but he is a radio man and shadows can’t talk so he does what everyone in hell does. He makes a deal to get his puppet life and a voice. Since it is a vessel though, it can’t hold all of his power without crumbling apart. But now maybe he doesn’t need the doll anymore. Maybe he can talk through his cane or he can make himself a new body. Well suddenly there really is no reason to have his power locked away like it is. So he is looking for the loophole he couldn’t add to the original deal. Because shadows can’t talk.

[aspiringnexu]

Okay, so, Alastor theory. As far as I know nobody's discussed why Alastor ever made such an apparently disadvantageous deal.

I mean, his power is apparently leashed. He cannot access his true strength. He essentially handicapped himself in Hell. Alastor detests not being in control, he craves power because it nets him control and therefore nets him safety and security, a very rare commodity for a demon. Even an Overlord.

So why the hell would Alastor make such a shitty deal? He's a dealmaker, he knows how this works, it can't just be the result of tricky wording, there must have been something else at play.

Additionally, I'm in the camp that its Eve that has something to do with it. Lilith makes sense of a sort but why would she leash Alastor and then have him help Charlie with a project that would piss off Heaven? She's Lilith, she knows that trying to bypass the initial judgement and redeeming yourself would upset the bigwigs in Heaven. She knows they don't like having their rules bent and twisted. She gains nothing from pissing off the Heavenly Host by indirectly helping her daughter. She made a mysterious deal with Adam to get into Heaven, why would she knowingly jeopardise that?

But why would Eve care? Simple. She feels like Lucifer and Lilith betrayed her by gifting her the apple from the Tree of Knowledge. They betrayed her and she was forced into a life of pain and suffering with a husband who she realised didn't truly love her and children who started to turn on each other the moment they could. And then that same husband (or ex-husband by that point) turns around millennia later and gets Lilith into Heaven.

What the fuck?

So Eve decides that the best way to sort this out is to do what Lilith supposedly did. Betrayal disguised as assistance. Charlie is a well-known bleeding heart by now, all Eve need do is find a way to stoke that altruism until it becomes a Problem that Heaven needs to solve. Poke the altruistic bear enough and that Problem will blossom into a Shitstorm that'll drag Lilith off of her cosy perch in Heaven to sort out her wayward daughter and try to avoid Heaven deciding to exterminate every demon in Hell. Plus it'll give Adam a headache which is only a plus in Eve's eyes. And what better way to help the Princess than gift-wrapping Hell's most powerful Overlord and depositing him on her doorstep?

Her ultimate goal might be provoking an all-out war or simply petty-revenge that'll eventually get out of hand but I digress.

How does she persuade Alastor to accept such a shitty, hampering, restricting joke of a deal?

Again, simple. She's in Heaven and as such has access to angelic steel and a plethora of souls. Including Alastor's mother. The only person he ever truly loved in his life.

I'm willing to bet Alastor would do anything to safeguard his mother. Even selling his own soul.

Of course there's still the seven-year gap to tackle but who says Alastor didn't spend those seven years in Heaven? Maybe Eve managed to smuggle him up there and disguise him, let him enjoy seven years of bliss by his mother's side before blindsiding him with her ultimatum. Makes the clipped wings comment more literal.

Just my thoughts, of course, but I really can't see why else Alastor would sign his own soul away if not to protect the one person he lets himself love. He hardly made the deal for power if the deal restricted his powers and he was certainly in no danger from the other Overlords. So he made the deal, he saved his mother, but that doesn't mean he's not gonna try to find a way out of it.