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Champions of Equestria

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I couldn’t come up with what they’re talking about, but it ain’t good. Probably something about crushing dissenters and what to have for brunch.
 
I started this drawing and halfway through started questioning it. Nightmare Moon is still evil, power-hungry and arrogant and would have to fight constantly to secure her reign after deposing Celestia. She is a tyrant in every way. I have a hard time thinking Twilight would forgive NMM, much less join her. I’ve read a few fics like that, but it usually had a heavy dose of “Celestia was really a tyrant all along!” and I’ve never been a fan of that idea. The one exception was pretty damn dark and basically Twilight had a serious case of Stockholm Syndrome. So yeah, in the Starlight-altered timeline, Twilight would either just break and be a recluse, be imprisoned, or be leading the resistance. Maybe… Maybe if Twi tried to get close to NMM to sabotage her, free Celestia, etc…
 
However, I could totally see the above image happening if NMM had won that initial fight against Celestia 1000 years ago. I don’t think it would exactly be a loving relationship of equals though.

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FanOfMostEverything
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@Rokesh  
The thing is, she didn’t necessarily fail. She just didn’t hatch Spike’s egg. Given the lack of other hatchlings waddling about Canterlot, the egg test is likely a test to see how prospective applicants handle failure, a la the Kobayashi Maru. She probably passed; she just didn’t become Celestia’s personal student.
 
Which, of course, means that her loyalty wasn’t necessarily as entrenched as it would be in the main timeline. That a usurper who offered knowledge forgotten for a millennium might sway Twilight to her side. There’s a story in here…
Twilestia
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Primo Victoria
“However, I could totally see the above image happening if NMM had won that initial fight against Celestia 1000 years ago. I don’t think it would exactly be a loving relationship of equals though.”
 
Yeah, Twilight would be the evil brains manipulating NMM into doing whatever she desired, plus she would be the dom in bed. :3
Rokesh

TwiLuna - the MasterShip
But Twilight failed her test for Celestia school, in this timeline.  
I see her depressed and locked in her room from the whole world. She can’t handle fails well, so she would become bitter on the whole world.  
So I can see how this can lead to joining Nightmare Moon, or even waiting for NM arrival, cuz Twi can see this as apportunity for her.
 
 
I actually was surprised that in season 5 finale we didn’t see evil Twilight, cuz such fail could definitely break and change her.