https://sure-hoofs-table.tumblr.com/post/159394880849/about-sure-hoof\#notes

Sure Hoof was an only child raised in Las Pegasus, never really close with his parents no matter how much his mother tried to be. His father was highly uncaring, often dragging him along to poker and blackjack nights at a young age. Watching those nights Sure Hoof started to develop an understanding of not only card games, but how to bluff and smooth talk which shaped him growing up. These nights only went on for a few years until his father got arrested for illegal gambling charges, leaving him to just be raised by his mother.

Years of exposure to gambling meant that Sure Hoof looked into it himself, starting to run his own shell game using some cups and a ball he had lying around at home with his school peers. He obtained his cutie mark at age nine after winning a particularly good bet (some valuable trading cards from a classmate), signifying his ability to read other ponies and his knowledge of gambling.

His lack of guidance from older ponies left him with somewhat warped moral values, this coming to realisation not just after winning more things off his peers but when a young filly in his class was so confident that she had figured out how to beat his shell game one hundred percent of the time. At just twelve years old, he suggested that she bet her virginity on that claim. Foolishly she accepted, only to lose when a smooth move from his hoof had the ball fall into the slightly open desk where she couldn’t see it. He took full advantage of her that afternoon, as well as telling her that if she told anyone what happened he’d make her regret it.

Keeping these excesses under wraps, Sure Hoof grew up and followed his own perceived calling at working in a casino much to his mother’s disappointment. He takes great enjoyment in swindling high rolling ponies out of their bits, even willing to cover some of the losses for mares on their own in exchange for sexual favours. Most recently though he’s had his eye on a much bigger prize, one that carries a phenomenal risk if he fails in any way.

But as his mantra goes, “preparation beats risk.”