
Originally Posted by
TM2-Megatron
Of course, that provides a lot of fun potential (probably not in the show; but in fanfics) for a time travelling villain trying to change the past. It's possible to link at least some of the main cast members together, had Dash lost the race and the rainboom never happened.
Pinkamena (she wouldn't have switched to Pinkie in this timeline) would've stayed on the farm, retained her conservative hairstyle, and not been driven mad by the rainboom's shockwave or developed her physics-defying powers. After taking over the farm from her parents, she'd decide to begin expanding the family business from simple rock farming to a more elaborate mining operation.
The boulder Rarity was dragged to by her horn never would've shattered without the rainboom, so she would've continued thinking her destiny is rocks... initially resistant to the idea, but eventually growing to accept it. Soon after finishing school, this would lead her to Pinkamena's farm, where Rarity would become her right-hand-pony and top administrator during the transition from farming to mining. Spending so much more time around rocks at this point, it would be inevitable that she'd finally discover her horn is actually sensitive to the gems inside rocks, rather than the rocks themselves. That would be just the kick-start the mining business needs, and Pinkamena would make Rarity a full partner and they'd begin buying up as much of the land around Ponyville and the Everfree Forest as possible.
Applejack would've stayed in Manehatten, eventually becoming a wealthy socialite moving in the same circles as her aunt and uncle. She could be one of the first investors in Pinkamena and Rarity's mining operations (having been let in on the secret of Rarity's talent), hosting fundraiser galas and otherwise assisting them in securing investments from other members of Manehatten's elite. The reason Pinkamena and Rarity would've chosen to confide in Applejack out of all the Manehatten elite, of course, was because they both somewhat remembered her from their schoolfilly days in Ponyville, before Applejack moved to the city.
After losing the race, Rainbow decided to give up flying for good, dropping out of flight school and confining herself permanently to the ground; living a mostly solitary life on the outskirts of Ponyville. She goes so far as to make her career beneath the ground, becoming an embittered, heart-broken laborer in one of Pinkamena's many mines.
Fluttershy still developed her love for the ground (this depending only on the beginning of the race, not Rainbow's victory), but not her special talent for communicating with animals; or at least not as quickly. I don't imagine things would've gone as differently for her as for the others, though, because even prior to the rainboom she was clearly getting along with all those animals extremely well. Given her personality, I do think she would've felt herself responsible for Rainbow's bitterness and self-imposed isolation. She would probably choose to live relatively nearby to Dash so she could maintain their relationship, keep tabs on her, and continue to make attempts to draw out her old spirit.
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