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Just HC, but I figure Hitch has had to throw his friend in the Maretime Bay lockup numerous times.

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Background Pony #9D11
Sunny reminds me of my younger activist days. That sense of righteous idealism, of unshakable optimism that things will get better if you just keep standing up for the things you know are right… It’s a sense of relatable nostalgia most people won’t have, but which definitely endeared the character to me right off the bat.
That being said, I hope they explore the problems that come along with it more than they did in the movie (which obviously just doesn’t have the time to explore interpersonal conflicts). Show us what happens when Sunny is just plain wrong about something. What happens if she rushes into action without consulting her friends, like when she bet the Pegasus crystal, but doesn’t come out on top in the end. (Really, she should have just narrowly lost the competition. It could have been the point where Hitch fully joins the team, not in support of Sunny, but in chewing her out in defense of the Pegasus and Unicorn friends he made unexpectedly…)
I personally like characters written as such that strengths and flaws are both just different shades of the same personality trait and Sunny definitely has something to be explored in that direction.
Background Pony #431B
@Background Pony #6880
True, Hitch even mentions something to Sprout about having to keep bailing Sunny out. Shame that she’s put in the position of having to continuously take advantage of his clemency. Seems Hitch really is the new element of kindness.
Background Pony #6880
OP weighing in:
I never figured Sunny was put up on any charges, rather Hitch just tossed her in the lockup for a few hours to cool off, like the drunk tank. He says in the film that she has few friends left, implying she’s burned some bridges. Hitch has probably stuck his neck out for her a lot of times and talked angry citizens out of filing formal charges.
That brings up another reason to lock Sunny up in the jail; to protect her from a mob.
Background Pony #77D1
Sunny definitely has some petty vandalism and disturbing the peace charges on her record. Possibly inciting a riot, though she may have gotten off lightly since she was inciting it against herself.
I mean, even if one ignores the fact that she snuck into a building we were specifically told she had been banned from, there’s still plenty of hints in the conversation she has with Hitch afterwards that she routinely breaks the law in some capacity or other.
Hitch Trailblazer: Do you have any idea how many bylaws you broke in there?!
Sunny Starscout: I’m sure you’re about to tell me.
Hitch Trailblazer: Actually, for once I can’t! Because there’s so many! [sighs] I tried to warn you. I can’t keep associating with some pony who breaks every rule and causes chaos wherever she goes. I’m the sheriff!
Just saying, I suspect somewhere in the Maretime Bay police department is a rather thick file with her name on it.
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Sunny definitely has some petty vandalism and disturbing the peace charges on her record. Possibly inciting a riot, though she may have gotten off lightly since she was inciting it against herself.