Conundrum

Andre Keston was always smart—smart enough to get teased in school for being a “brain,” and smart enough to study computer science and mathematics, becoming an expert programmer and systems designer. Andre was a problemsolver, known for tackling the most difficult technical challenges and overcoming them. Unfortunately, his intellect and his technical abilities weren’t matched by his social skills. Andre dealt with being an intellectual geek by adopting an elitist attitude toward those he considered his mental inferiors, which was to say nearly everyone. It won him no points with his co-workers and left him with no real friends.
That didn’t matter, according to Andre. He was satisfied with his work and with being one of the most in-demand programmers and designers in the business; he was riding high on the dot-com boom, making more money than he knew what to do with. He even saw when the dot-com bubble was ready to burst, and protected himself. It seemed like there was no professional challenge Andre Keston couldn’t overcome. That was the problem; he was deadly bored, lacking intellectual challenge and stimulation.
When a mid-level USNet executive insulted the insular Andre, he adopted revenge as his new hobby. He systematically set out to ruin the man, and his plan was so well crafted only his victim knew who was really behind it, but could never prove it to anyone else. It was a rush of power like Andre Keston had never known. He was clever enough to outwit anyone and to do whatever he wanted.
It wasn’t long after that the mysterious underworld figure known only as the Conundrum began offering his services to certain crime families, as well as pulling some jobs on his own. He always left clues in the form of puzzles or riddles, challenging the authorities to figure out his schemes. Although the police were left baffled, Raven II was not. She matched wits with Conundrum and figured out who he really was. Andre Keston was arrested and jailed.
Prison life changed Keston. It had all been a game before, but now it was more than that. Conundrum was a true outlaw, outside the society he disdained. He would prove his superiority and get his revenge on the Raven and everyone else who’d ever taunted him. Over the years, Conundrum has proven remarkably adept at prison-breaks, so much so he was most recently incarcerated at Blackstone Island. However, he was later transferred to The Providence Asylum, diagnosed as socially maladjusted with a psychological fixation on his intellectual games as well as on the Raven. After months of treatment, Andre Keston was pronounced cured. A parole board released him from custody, and he has become a well-paid consultant in the high-tech field once again, working primarily from his midtown apartment over the Internet.
The Raven has kept a close eye on Conundrum, and wisely so. The Prince of Puzzles is by no means cured; he has simply figured another way out of his predicament. Conundrum is operating behind the scenes once again, careful to cover his tracks. This time, he’s certain he won’t be caught. This time, his plans are flawless. Of course, he hasn’t accounted for the possibility of any new heroes coming along to spoil them.
Conundrum is a behind-the-scenes mastermind. Physically, he’s no match for most heroes, but mentally is another matter. Conundrum is given to elaborate plots designed to make heroes think, particularly putting them into various deathtraps and difficult situations. He is a master of misdirection, innuendo, and trickery.
The typical crime-spree for Conundrum is a series of seemingly random crimes with complex clues left behind for the heroes to unravel. Normally these are hints about what Conundrum’s next crime will be, or ways the heroes can find and stop him. Sometimes Conundrum uses these clues to lure heroes into a trap, which itself may contain a clue as to the villain’s whereabouts. Conundrum simply can’t help leaving these clues. It’s not really the crimes that matter, it’s the thrill of outwitting his opponents, of proving himself the intellectual superior.
Conundrum is also known for working as a consultant for other criminals, providing them with foolproof plans, deathtrap designs, and cunning schemes. Again, it’s not the money he gets paid for these things; it’s the challenge, the thrill of the game. In addition to providing resources for other criminals, Conundrum may even take to disguising his own activities as “consulting work,” using another villain’s modus operandi (something Conundrum’s fellow criminals won’t find endearing).
Conundrum feared the retirement of his old foe the Raven would deprive him of his opportunity for revenge, but the criminal puzzle-master put all of the numbers together to figure out that the former Raven was, in fact, Callie Summers, the new mayor of Freedom City! Although he could have simply exposed the truth, that had the potential to backfire. No, if Freedom City meant enough to the Raven to give up her costumed career to protect it, then Conundrum would find a way to destroy it, to undo every good thing Mayor Summers sought to do. Only when Freedom has become a social and financial ruin, with the blame laid at the feet of the Summers administration, will Conundrum find a way to let his old foe know exactly who is responsible, before delivering the coup de grace.

Physical Description

Specialized Equipment

A rarity amongst costumed criminals, Conundrum has no powers. He is all about misdirection and elaborate—sometimes overly elaborate—tricks. Ideally, heroes only see or hear him on remote broadcasts and recordings, without knowing where he actually is or what he is doing at the time.
Conundrum creates traps tailored to his foes, when at all possible, although he has a variety of “all-purpose” deathtraps. Working with villains like Toy Boy and the Foundry in the past has given Conundrum a considerable arsenal of technology and more than a few favors to call upon. He also has quite a substantial amount of wealth and corresponding influence, which he uses to outfit any schemes where a client is not footing the bill. Conundrum stages the occasional robbery or other money-making scheme to supplement his resources, but mainly to keep himself sharp and in the game.
Conundrum’s current schemes often involve complex blinds and decoys. He’s fond of finding ways to telegraph to his foes that he is involved, while at the same time securing iron-clad alibis for Andre Keston, suggesting that a “copycat” criminal is responsible; even then, he won’t be able to resist telling targets the truth, but will save the “big reveal” until the end.
Conundrum is also fairly well-trained as a marksman and unarmed combatant; foes who underestimate his ability to defend himself may be in for a surprise.

Mental characteristics

Intellectual Characteristics

Some of Andre Keston’s old associates would say he doesn’t have a personality to speak of; certainly Conundrum is a cruel and self-centered egotist, with virtually no regard for anyone else’s feelings or well-being. Therapists diagnosed him as obsessed with his self-image as a brilliant problem-solver and his need to compete and prove himself more capable than anyone else. The elements of Conundrum’s personality that can be relied upon are his obsession with puzzles and complex plots, his superiority complex, his need to gloat and lord any achievements over his foes, and his vengeful streak, directed at anyone who manages to overcome or, worse, outwit him.