A pony sat at a table outside the St. Amble Cafe in a sun-kissed cobblestone street, sipping lightly at a cup of coffee. A lit smoking cigarette sat in the ashtray on the table before him; the smoke that wafted off the lit stick smelled of heady Saddle Arabian perfumes. A light wind rustled the leaves of the oak trees spaced with precise regularity across the sidewalks, but the pony did not acknowledge it. The scent of the cigarette, the taste of the freshly-brewed coffee, the gentle warmth of the sun embracing him...he felt none of it. His mouth remained in a thin, neutral line, and no emotion showed at all in his abyss-black eyes.

They called him the Chessmaster back then: his name had not yet gained the fame and fear that he was known for now. The title could not have been more appropriate: every crime he planned was set up and executed with perfect precision, with nothing left to chance. A few members of the underworld had started a rumor that he was able to see the future. The thought caused the dining pony to snort disdainfully. Dummköpfe.

It had been an amusing diversion at first. Pitting his mind against the law, continually testing them to see who was better. He remembered the first crime he planned, when he was merely fourteen years old: the murder of his parents. It had been easy, extraordinarily easy: a little unexpected mogul in the ski path right in front of a sheer cliff, and then all he had to do was play the mourning child and let the world write it off as an accident. The fortune he inherited was certainly quite nice, but that hadn't been his motive: he'd just wanted to see if he could do it. And he'd done it.

That was the first of hundreds. He'd loved the challenge, the thrill he got from playing other ponies like pawns on a chessboard. And over the years, he got bolder and bolder, the size of his board and the number of the pieces increasing exponentially over the years. And he always won.

Therein was the problem. It had became too easy, the game too predictable. There was nothing new in the world of crime and law, nopony to match wits with him, no unique, special thrills to delight in. And bit by bit, the little pleasure that he depended upon to forget that he, like all ponies, was trapped in a pointless, empty existence, was taken away from him. It had been over a year since he had last smiled; he had not felt anything for almost as long. Every morning, it was becoming harder and harder to find any reason to pull himself out of bed.

Recently, he began to wonder if he should make it a little easier for his opponents. Maybe then he could even up the game a little bit and finally find somepony worth playing with. And for that, he turned to one of the few things he truly enjoyed: riddles and puzzles.

One of his favorite methods of communicating with his pawns was with a special code that consisted of selecting letters from the daily crossword. So the day before, he had sent a note to the local Guard precinct with a code that, when put through the day's crossword, revealed his clue: "What has four wheels, thirty bouquets, and flies?"

The answer was, obviously, a garbage cart. A garbage cart carrying a set of valuable flower paintings stolen from the Gritish Art Museum. Specifically, the garbage cart across the street from where he was sitting. As he watched, a set of surly ponies carried large garbage bags out of the back door of the museum and tossed them into the stinking wooden cart that creaked beneath the weight of several blocks worth of trash. Within the bags that these ponies were carrying was a set of paintings, statuettes and other exhibits stolen from the museum. The stallion glanced up and down the streets. Plenty of shoppers, strollers and joggers to be seen, but not a single Guard.

He sighed. It was too easy. He'd given it a try, and it hadn't worked. What was the point anymore? There was a perfectly good bridge not far from here, sitting 200 feet above the icy cold waters of the river. Perhaps there he could finally...

Suddenly, there was a loud whirring noise and the sound of something impacting against a skull. The largest of the false garbage ponies collapsed the ground, unconscious; the bag that he was carrying dropped and spilled open, revealing the stolen stamps that it had been carrying. Every head turned to view the stranger in the green vest and gray trilby running up the street, catching a spinning boomerang in his hoof as he sprinted towards the garbage pony. The thieves, sensing this was an attacker, immediately drew knives and ran forward to meet him, only to find themselves on the receiving end of a telescoping baton.

The watching stallion stared at this intruder in amazement, watching as he easily weaved through his opponents, fluidly moving from attack to defense, from enemy to enemy. He committed every memory to detail, from his magnifying glass cutie marks to the old, fraying black band around the trilby, but it was the stranger's eyes that attracted his attention: gray as stormclouds, hidden behind midnight black bangs...full of a rage like he had never seen before. This stallion had brains—that was evident from the fact that he had solved his riddle—and yet, look at him: hitting and hitting with the force of a wild animal controlled with the cold calculation of a machine, looking like he just wanted to hit back against the whole world, and hit where it hurt the most.

"Fascinating," Zugzwang whispered softly, slowly standing as he watched the pony throw the last thief to the floor and strike him twice over the head with his baton. For the first time in over a year, he felt something: a strange sensation he could not identify or put a word to, but that made his heart beat against his ribs like a drum and a warmth spread to the tips of his hooves.

For the first time in over a year, Zugzwang smiled.

He had finally found somepony to play with.

Author's Notes:

Tonight, we are pleased to give you the story of how Zugzwang met Phillip Finder and began their long rivalry. Inspired by Batman: Lovers and Madmen, this little story gives you a close-up look on Zugzwang's personality and mindset, and what really drives him.

This is officially all of the information that I'm giving you on Zugzwang's history: I feel that he doesn't really need a fleshed-out backstory. He just needs to be who he is in the stories: Equestria's Black King of Crime.