The Riddler (Arkhamverse)

"Think of me as an information broker. I've got data handlers everywhere-feeding me all kinds of interesting stuff!."

- Enigma

Though his real name and identity are unknown, the man who would soon go by the alias Edward Nigma is clearly a man who has spent a vast amount of his life studying, exploring & memorizing all the knowledge he possibly could. Being raised by abusive & neglectful parents, he strived to be the most intelligent man alive. His parents (primarily his father) refused to believe he could ever become smarter than them, often accusing him of cheating whenever he succeeded in school academics or trivial games. This may have been what caused his inferiority complex to become so deep that he feels compelled to always leave cryptic clues to anyone worthy of his games in attempt to prove both his honesty and his intellect.

Batman: Arkham Origins
Black Mask is set to appear in Batman: Arkham Origins as the main villain and antagonist, having placed a bounty of $50,000,000 on the Dark Knight himself and bringing in eight of the world's most deadly assassins, including Bane, Deathstroke, Deadshot, Copperhead, Electrocutioner, Firefly, and Lady Shiva, to Gotham City for one night on a particularly snowy Christmas Eve to kill Batman.

This bounty and enlistment of assassins sets in motion a chain of events that leads Gotham down a road of death and destruction as Batman faces, for the first time in his career, the most iconic of Gotham's villains and criminals that would go on to become his immense rouges gallery and the most notorious inmates within Arkham Asylum.

At this point in the Arkham Continuity, Black Mask is by far the most powerful man and crime lord in the city, possessing immense wealth and resources and controls Gotham's criminal underworld with his massive gangs. With corrupt public officials, such as Commissioner Loeb, and countless bent cops on his payroll, Black Mask also effectively and completely controls the Gotham City Police Department, with the exception of Captain James Gordon and a few others, allowing him to easily stay out of prison with any evidence against him mysteriously going missing and witnesses ending up dead.

With Black Mask using sadistic torture, fear, and punishment to exert his control over his followers, enemies, and the entire city alike, and the entire Gotham police force serving as little more than a secondary gang for his forces, few stepped up against Black Mask, despite most believing his involvement in the numerous crimes he has been alleged, but never convicted of, to have committed.

Having wiped out most of the competition and begun consolidating his power, Black Mask issues forth a crime wave with his gang to capitalize on his reign over the city on Christmas Eve, while his contracted assassins attempt to put an end to the one man capable of ruining his plans and hold over the city once and for all.

Forming an alliance with other criminals within Gotham City, including newcomer to the criminal underworld Oswald Cobblepot, also known as The Penguin, who agreed to assist in his plans for his own purposes, Black Mask also seeks to completely wipe out the entire Falcone Crime Family, one of his last remaining, competing adversaries.

Additionally, it appears that Black Mask's actual mask is not yet attached to his face, but rather a disguise he wears as part of his persona when heading up his criminal activities. This allows the villain to publicly run his company as Roman Sionis and keep himself from being connected to any crime, while also using his businesses as a front for drug trafficking and other illegal operations.

It is unknown what Black Mask's true motivation is for suddenly targeting Batman, aside from keeping the hero from interfering with his rise to power, but it has been hinted to be on a more deeper level and serves as one of the story's primary mysteries that will become more clear over the course of the game.

Batman: Arkham Asylum

 * See: The Riddler (Batman: Arkham Asylum)

Batman: Arkham City

 * See: The Riddler (Batman: Arkham City)

Trivia
To be added