|First appearance||March 14, 2012|
“ Sometimes, you look at yourself and realize... that you hate what you've become.”
Former Spymaster and Talented Architect.
Brash and overconfident, Sly gives off an aura of utter smugness. While on the surface he is utterly implacible, underneath is a deep wound and terrible doubts which may never fully heal.
Sly was born in Cloudsdale. He never discusses his real parents with anypony. His real father's identity was a drug runner for the Leaf Cartel, his mother was one of the clients. The circumstances leading to Sly's birth are unknown. Practically raising himself, Sly developed a fierce independant streak, and quickly learned that if there was anything he wanted, he should simply take it.
Developing a reputation as a bully and a thug, Sly would eventually encounter a young Night Light. The two had an encounter that ended with Night in tears, and Sly walking away with his lunch money. But the next day, Night sought out Sly, not for retribution, or repayment, but to offer to be Sly's friend. Sly resented the little tag along at first, but Night's attitude wore on him, and then grew on him, causing Sly to grow fiercly loyal to the other colt. Night's parents, Noble Light and Guiding Light, looked into his family and past, and agreed to do what they could to help the colt. Only their oldest daughters, Sun Smile and Mint Creme learned the truth, and the Light Family did what they could to treat Sly like a son.
Over time, Sly grew to be a fierce protector of Night, who's naiveity and gentle nature made him something of a natural target. Eventually learning a talent for constructing and planning, he paid his own way through college, graduating alongside Night Flurry with an Architecture and Engineering Degree.
He moved to Whinneyapolis, stating that Cloudsdale held too many bad memories. There, he joined a firm and began to rise in recognition. And with success in hoof, he began to talk to ponies in the area, and began to follow through with a life obsession, tracking down his real father's identity. This began the construction of an intricate and massive spy network which Sly would sit at the center of.
While Night Flurry continued to stay in contact with Sly, Sly himself was far too busy to write back, establishing his network, going out on his own to verify information and contact ponies. He would use whatever advantage he needed, sleeping with ponies, killing others, even working hoof in hoof with the Manehattan Mob and Leaf Cartel itself. There is reason to believe that he or his contacts were responsible for tipping the Mob off to the location of Nassy at one point in her flight from Manehattan. While he maintained that he was doing many of these things for the greater good, the line was crossed more and more often as time went on, and the information itself became more valuable to Sly then it's purpose.
Night Flurry remained in contact with Sly, writing him letters. When the focus of his letters began to shift to an infatuation with a mare, Sly began to look into her past, and uncovered ties to the Leaf Cartel. With that, he set out for Ponyville to catch up with his friend. There, he met with Night, but also met with Dusky Down, who he attempted to talk into letting Night off the hook, or his infatuation would get worse.
Sly returned to Ponyville several months later at Night's request, where he would assist Night's sister Spring Showers in doing Night's job while Night was away on a trip across Equestria with Dusky. Sly was present in the confrontation with Autumn Blaze, which, when Night's initial trip failed to launch, would result in him traveling to Zebra Lands, where he would attempt to undermine Aqua Brandish's empire from within.
When he returned, he moved into Night's house, dislodging Spring. But as Sly made himself at home in Ponyville, he didn't do much to make any friends, seeing them all as potential threats to him. He kept extensive documentation on Night's friends, picking them apart to find ways to exploit or blackmail them in case he ever needed a way to stop them. But the arrival of one pony going by Divine Will, would destroy this and twist it against Sly. Secretly a changeling bounty hunter, Divine Will ensnared Sly, solely to take his home as a base of operations and feed upon him, but she soon discovered how valuable he really was.
Stuck to the wall in Night's guest room, Sly was kept prisoner, aware of the Changelings as they proceeded to torture him. Sly's mind was shattered, his defenses torn apart, and what little will he could muster he pushed into breaking free at last, rushing to the bar to warn Night's friends. He awoke in Ostfriesen, and after recovering physically, Sly attempted to recover mentally, his former bravado shattered, he did what he could to repair Night's home, make what amends he could, and prepare to confront Night Flurry.
In his time after the Changeling attack, Sly attempted to find himself, and in doing what repairs he could to the lives of others. Giving up much of the Spy life, Sly slowly moved all of the assets and information he had to a new Spy Master, completely leaving his organization. He developed a deep an truly powerful friendship with Sunrise. From there, he helped gather ponies to assist Night and Dusky in confronting the Banshee, before at last coming clean with Night Flurry, who despite initial misgivings, would forgive Sly.
Sly returned home to Whinneyapolis, and from there, he would hire Sunrise, bringing her to town and spending more and more time with her, until at last she convinced him to express love. The two have been together since, slowly developing a strong relationship bond, although Sly continues to have misgivings that he may only be a runner-up for Sunrise, when she's around he can rarely think on these doubts.