Star Buck's was born into a life of relative privilege and ease. She did not have to toil in the earth. She did not worry about court intrigues. She did not endure the harsh military training of the pegasi. She did not worry about where her next meal would come from or whether she'd be cut down by some strange beast while on a patrolling mission.

She lived on the outskirts of Manehattan, attended school, and listened to her father's stories of the glimmering capital of the unicorns and her mother's tales of life on an isolated farm on the outskirts of civilization.

She had her entire life planned out, even if her cutiemark stubbornly refused to appear.

That is until Archmagus Sunbeam Sparkle introduced her to Platinum Dancer. The bloody Equestrian Civil War that tore her family apart was nothing compared to the way that mare changed her life.

Part of Chengar Quordath's Winningverse and set during the time of The Lunar Rebellion aka the best work of fiction on this entire site.

"It's bad enough you lost to that transplant from Trottingham, but imagine if you'd lost to one of those blank flanks. As a Rich pony, you must always think of your social standing. That starts here in Ponyville and reaches all over Equestria. Don't ever forget that, Diamond Tiara. Ever!"

"I thought it looked a little country."

"See how they hang on every word that I speak
My approving glance is what they all seek
I'm the creme de la creme, not just another Jane Doe
I'm the type of pony every pony should know"

Spoiled Rich and Filthy Rich attend a dinner party at Fancy Pants's new summer home in Ponyville. Set before Diamond Tiara was born.

"It was a strange coincidence," I said.

"But it wasn't a coincidence at all."

"Why not?"

"Rarity bought that house so that Blueblood would be just across the bay."

Yes, this is Great Gatsby with ponies. Yes, Derpy is Dr. TJ Eckleberg.