HELLFIRE

CLARIFICATION

Yes, it still seems like a stupid decision to stand with Mal but not all OCs are perfect. I wanted to make Maddy's flaw was that she gave too many chances and cared too much on an island that didn't care at all. A lot of people struggle to cut off those they know are toxic to them and Maddy provided someone they could relate to.

I'm sorry this decision angered so many of you but I hope you can perhaps understand a little of why this was done. If it helps, it angers me too. I wrote so many scenes of Maddy telling them all to go fuck themselves but none of them seemed right when I remembered how caring Maddy was. Feel free to still rage away in the comments but I hope this provided some clarification.

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2. MADDY STAYS IN AURADON. TWICE
Yes, Ben was supposed to originally send Maddy back to the Isle but for four months after Uma escaped, the council deemed it unsafe to open the barrier. Ben had numerous meetings regarding the arrival of more VKs, the barrier and any other logistics. In that time, Maddy had no choice but to begrudgingly stay in Auradon. And, believe me, she kicked up a fuss. However, in that time, she takes some classes, makes some friends and gets a taste of what Auradon provides.

When the barrier starts opening so the original VKs can take supplies to the Isle, Maddy goes with them in the hopes she can see Harry. She doesn't see him or Gil but she runs into a group of pirates. They tell her that she's not welcome after what she did. Assuming that Harry has taken over as Captain, she guesses the message is from him. Ben worries about her safety after that and asks that she remain in Auradon (on Mal's wishes).

On top of that, Maddy is scared. She stays in Auradon for the time being because she can't face the pirates. She betrayed them and knows she wouldn't be safe on the Isle without a crew. She's guessing that Harry and Gil hate her for what she's done, and couldn't bare it if she bumped into them and heard the words directly out of their mouths. So, she stays on Auradon for a little while longer and then the events of D3 happen anyway.

Once again, I know it doesn't make sense to you readers but this is because I'm a bad writer and didn't divulge this information. Sometimes I forget that what's in my head isn't what is always written down. Maddy is convinced that she doesn't have a life left on the Isle, and tries to pick the broken pieces of herself up at Auradon. She's also excited to be a part of the VK program and help the new VKs adjust to life on Auradon as she's the newest one there.

She then chooses to remain behind a second time after they save Auradon in D3. This wasn't a decision she made lightly. She knew Harry was going back to the Isle and she didn't have much time to choose between him or freedom. Maddy wanted nothing more than to be with Harry but she wasn't sure she could go back to living on the Isle.
She makes the decision to put herself first. She doesn't think about Harry or Mal but herself. At Auradon, she was known for who she was as a person and not for those she was associated with.
On the Isle, she was Maleficent's daughter or one of Uma's crew. In Auradon, people had come to know her as Maddy. They didn't see her as Mal's sister but as the woman who had managed to get a place on the royal guard. She chose to remain at Auradon for the life she had worked hard for by herself.
Also, because she didn't have time to think about the decision. She didn't want to choose the Isle just for Harry and then come to resent that decision. Because, she would end up resenting Harry. At least at Auradon, she had access to resources that could help her see ways around the barrier.

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3. MADDY BETRAYS UMA
Only one commenter saw the reasoning behind this so I don't think I explained it very well.

Maddy comes up with the idea to trick Uma by giving her a fake wand. This isn't because she wants the VKs to win, it's because she doesn't want the barrier to come down.
Life on the Isle is crap but it's a life those living there had adjusted to. Quite a lot of them were uncomfortable with the idea of the barrier coming down, and were scared of what it meant.
Many of them wouldn't have been allowed to continue with their lifestyles - for example, pirates would've been disbanded - and would've struggled to acclimatise. Furthermore, many villains would've been after revenge, thus resulting in harsher consequences on their children.
She knew Uma wanted revenge, not to peacefully attend classes and bow to a King. She's also scared of what mixing with Heroes would mean for her friends. For example, she was worried about what Beast would do to Gil.

Maddy ends up feeling incredibly guilty for deceiving then and struggled with whether or not to tell them. In the end, her love for them wins out and she tries to tell Harry before It's Goin' Down. She never gets the chance to but she still believes she was doing the right thing, she just felt guilty about not helping her friends.

This decision also shows a major difference between Mal and Maddy but ultimately, how similar their minds work. Mal closes the barrier to keep Auradon safe from the villains and chooses to act like any other prince or princess. Maddy wants the barrier to remain shut to keep the Isle safe from Auradon because, to the VKs, the "heroes" are the villains of their story. She knows that most of them are good people who will only be hurt by the prejudice views of Auradon.

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4. MADDY'S RELATIONSHIP WITH UMA
Uma offered Maddy a place in her crew because it gave her power to finally have an infamous VK under her rule/control.
Eventually, they develop a mutual respect for each other and discover they're a lot alike. The form a genuine bond of friendship but Uma still likes to remind Maddy that she's above her in the hierarchy.

This causes tension between the two because Maddy doesn't like to be ordered around or told what she can and can't do. Maddy has no issue telling Uma when she disagrees with her.

One of the ways Uma reminds her that she's captain is through Harry. Harry has undying loyalty to the daughter of Ursula because she gave him a crew and a position of power. Therefore, he does what she asks when she asks. Uma will deliberately ask him to do things when she knows he has something planned with Maddy.

Uma is furious that Maddy betrayed her and abandons her in Auradon on the ship, instead of taking her with her. This only adds to the tension between the two but when Uma starts relinquishing some some of the control in D3, they remember why the became friends in the first place. All the want to do is help people.

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Anyway, I don't expect this to change anyones mind but hopefully just clear a few things. Please let me know if you want anything else explained but also,
Go easy on me, guys.
This was one of the first things I wrote fully and I've since improved.