I have a theory… Wind Rider and Windy Whistles are siblings. I mean, good heavens, his color is IDENTICAL to both Windy and Rainbow. Heck, at first I thought it’d be interesting if he turned out to be Rainbow’s dad! But after “Parental Glideance” came out and we saw her parents, my head canon kind of died out.
 
Then I thought about it some more and this image popped into my head!
 
STORY:  
Windy Whistles found herself walking into a dingy old bar late one night. Rainbow’s latest performance had just finished and Bow Hothoof was off proudly boasting about his daughter’s accomplishments. Tired of all the hullabaloo, Windy left the chaos and soon enough approached the counter for a late night drink. It was then that she heard a tired, familiar grunt sound from not too far away.
 
“Did Rainbow do well?” he asked.
 
When she turned her head, she could not hide the surprise of what she saw from coming onto her face. There, sitting at the counter, face rough with unshaven stubble and eyes long turned bloodshot, was her older brother Wind Rider.
 
“Did she beat my record?”
 
Windy felt her breath still in her throat. Sitting not four feet away from her was the pony who almost destroyed her family when he walked out. The pony they all swore to never speak of again despite his amazing abilities, the pony who killed their mother from heartbreak. She didn’t know how to react to seeing her once proud brother stooped over the bar like an old drunkard, but she soon found her voice and let cold, furious indifference stick to her words.
 
“Yes, Wind Rider,” Windy growled. “She did beat your record. Surpassed it even.”
 
“Figured she would. She’s got a lot of her uncle in her.”
 
“No,” Windy sneered. “She’s got a lot of her mother in her. After all, she’s still here. She hasn’t walked out on us.”
 
“Yet…”
 
Windy snorted, growing wild with anger, and stormed out of the bar before sending one last hateful glance towards Wind Rider. His golden eyes locked onto hers, but all she could see shining back in them was a hollow shell of an old stallion long past his prime. Tossing her bright mane, she left him there; alone with nothing but his mug of hard cider and the few bits he had left in his possession.