Edward Nashton

== Biography ==
=== Early Life ===
Records indicate that Edward Nashton was born on October 22nd, 1974. He was left abandoned at a fire station in Gotham, and was then put into the Wayne Foundation Orphanage. At a young age, Eddie watched the public mourn for Bruce Wayne, a spoiled rich kid, who lost his parents, while he and the other orphans grew up with less than him with nobody paying attention to them. This began his disillusionment with the wealthy, as he began vying for their destruction.
Eddie was disliked by most of the other residents and as a result was often beaten up by the other kids. He was mostly picked on for his glasses, but also because Eddie was compulsively obsessed with puzzles. He used them to sharpen his brain and distract him from his crumbling surroundings. He perfected his mind on rubix cubes, crossword puzzles, sudoku, brain teasers, and the like.
In high school, Eddie was an outcast, but his wit was quick and his intellect high. He proved it when a scholarship contest was announced in which the recipient had to solve one of the world’s most difficult brain teasers. Eddie solved it and used the scholarship to go to Gotham University, feeling like he was at long last moving up in the world.
He got a degree in criminal justice and became a forensic examiner in the GCPD. Eddie attempted to ignore his trauma and his crippling undiagnosed OCD, masking it with his intelligence. While working there, he caught eyes for Kristen Kringle, a records keeper. However, she was involved with Officer Tom Daugherty, who often ignored Nygma, and was known for accusations of police brutality.
In his off-time from the GCPD, Eddie began investigating independently. He discovered that the mayor of Gotham, Henry Claridge, was having affairs with prostitutes he picked up from Oswald Cobblepot’s club, who served under Carmine Falcone.
Suspicions grew around Eddie, and several officers didn’t trust him, so Daugherty decided to take care of him. Daugherty cornered Eddie as they were leaving work and attempted to push him in front of a train. Eddie escaped, with Daugherty pursuing him. Eddie ended up catching Daugherty off guard and stabbed him to death. He calmly cleaned the scene of all evidence and then fled.
=== Enigma ===
Kristen mourned Tom’s death. Eddie tried to comfort her as much as he could without arousing suspicion. In secret, Eddie would go out at night, dressing himself in a ski mask and hood, and would pick off aggressive men. He seemed to develop a second voice in his head, one he called Enigma. Enigma would take over, making him more confident, and he would claim victims, carefully cleaning the scene and leaving no trace. Nobody knew there was a serial killer stalking Gotham.
Eventually, a year had passed and Eddie asked out Kristen. For awhile, things were fine, it seemed like the best parts Eddie and Enigma had merged, and Eddie had confidence. He ended up legally changing his name from Nashton to Nygma, believing himself to be one full person. Then, one night, while drunk, he confessed to Kristen that he had murdered Daugherty, and continued to kill, but with her he had stopped. Kristen attempted to flee, and the worst parts of Enigma came back, and Eddie killed Kristen.
Around this time, Batman debuted.
Eddie took the identity of Batman to be the ultimate challenge, and in secret, he would steal forensic evidence from the GCPD in an attempt to discover Batman’s true identity. However, he continued to constantly be unsuccessful.
He got to work directly with Batman when Lieutenant Gordon secretly recruited Nygma to allow Batman access to forensic evidence when he was attempting to figure out who murdered Henry Claridge, which turned out to be the Joker. Eddie also found the Joker to be a riddle, and attempted to find his identity, to little avail.
Following Claridge’s death, Don Mitchell became Mayor. Eddie had continued investigating the web of corruption in Gotham, and he knew that Mitchell was one of Falcone’s lackeys. Eddie later noticed the drug trade increasing in the GCPD, as they continued secretly funneling drugs for Falcone. Eddie tried to tell Gordon about it, but Arnold Flass threatened him, so Eddie backed off.
Within a few years of Batman’s appearance, Falcone and Maroni’s operations had collapsed, and a massive power vacuum had opened in Gotham. Eddie decided it was time to bring back Enigma. Eddie had been assembling his own hit list of people in power who continued to aid and abet the mafiosos, whether it be dirty cops in the GCPD, lawyers willing to turn the other cheek, or lower-level crime bosses like the Penguin.
=== The Riddler ===
He started off picking off people on the list. Small at first, like bagmen and dealers. When the crimes went unnoticed, it ticked Eddie off. Listening to the evil side of his brain, he created the persona of the Riddler, leaving behind clues at the scene of the crime. At first, it started as a gimmick, but grew to be a compulsion.
Eventually, Batman put together the clues and deduced that there was a serial killer, connecting them all to the Riddler. Eddie continued to evade capture and avoid suspicion. However, when Julian Day began mimicking Riddler’s killings, it led to his downfall. In an attempt to outdo the “Calendar Man”, he slipped up, giving away his identity and resulting in his capture.
Eddie was imprisoned in Arkham Asylum. He did not receive the care that he needed. The psychiatric staff was unhelpful and ill-equipped (and in the case of Harleen Quinzel - otherwise preoccupied). When Poison Ivy executed a break-out at Arkham, Eddie took it as his chance to escape.
He stuck around Gotham, but he kept a low profile. He ended up falling into favor with Oswald Cobblepot, who used him as a logistics coordinator for his weapons deals, in return giving him a substantial piece of the pie. Eddie began to form his own connections in the field. He recruited Nina Damfino and Dierdre Vance as his lieutenants (and lovers).
He splintered away from Cobblepot and formed his own gang, dealing in information. Eddie became a master computer hacker. He took the faux name of Cayden James and used that name to wreak havoc in Star City, nearly exposing Oliver Queen’s status as Green Arrow, were it not for Felicity Smoak stopping him.
As usual, Eddie’s ego got the best of him. As Cobblepot ran for mayor, he attempted to kill him, but slipped up and was caught by Batman. This time, the court wouldn’t hear an insanity plea, and instead sentenced him to Belle Reve Penitentiary, where he got wrapped up into Task Force X.
During his mission on Task Force X, collecting Brainiac tech from an Intergang stash house, he figured out how to disable the bomb in his neck by stealing prototype electrocution gauntlets from the storehouse and shocking himself in the neck with them. When fellow operative the Hyena tried to stop him, Eddie put a bullet between his eyes and made his escape.
He returned to his gang in Gotham and found that Nina was pregnant, and he soon welcomed his daughter, Evelyn into the world. Evelyn grew up in Riddler’s little gang. They would occasionally have to move when Batman caught wind of one of his safehouses.
When Riddler was approached by the Joker with a proposal, he was too scared to say no. He offered up one of his safehouses to him for unknown use and then agreed to jerry-rig a livestream into all of Gotham Square - unaware the clown prince of crime would be using it to showcase the torture and murder of the second Robin. To cover his ass, Riddler hauled his little family to Metropolis.
The Puzzlers, as they became known, hung around in Metropolis for a while. Eddie’s suave attitude allowed him to broker deals with the 100 Gang and Intergang. With Superman on sabbatical, crime escalated, especially in the Suicide Slums, where Riddler made a large stake. However, as more Kryptonians turned up in the city, operations had to be scaled back.
When he caught wind that a schmuck by the name of Cluemaster was copying his usual M.O, Riddler carted his crew back to Gotham to put him in his place, kidnapping Batman and the third Robin for one very bizarre quiz show between him and Cluemaster. Cluemaster’’s daughter put a stop to the operation and saved Batman’s neck.
Riddler escaped - but the rest of his family was not so lucky. Nina, Deirdre, and Evelyn were all picked up by ARGUS. Unbeknownst to Eddie, Deirdre and Nina were given an offer; they could go free with their daughter, if they gave up Eddie. They complied and got off scot-free, and Eddie was arrested when ARGUS’ Privateers raided one of his safehouses.
Eddie landed himself in Blackgate. During a medical screening, he learned he had an aggressive brain tumor. Lucky for Eddie, he didn’t sit around a cell for very long. On May 8th, 2016, the League of Assassins led a breakout at Blackgate, letting Eddie go free again. He quickly found the coordinator responsible, which happened to be Deathstroke. Having researched the League of Assassins, he asked if he could speak with Slade’s boss.
When he met Ra’s al Ghul, he offered all of his services to them in exchange for a one-time use of the Lazarus Pit to cure his cancer. Aware of Eddie’s slimy status, Ra’s was hesitant but agreed. They utilized his hacking ability to eventually steal Batman’s Agamemmno Contingency, and Eddie was a leading designer of the software that would go on to be used on the OMACs. He was also part of Thomas Morrow’s think-tank when he created Tomorrow Woman.
When everything with the OMAC Crisis went haywire, Eddie thought his debt to the League had been paid - and so he skipped town. He went underground for a few months. Batwoman and Huntress got on his trail when a series of ritualistic killings in the name of the Church of Crime appeared to follow his M.O, but it turned out to just be his daughter trying to pin the blame on dear old dad.
Since then, it appears as if Eddie has turned over a new leaf. He gets in contact with ex-Task Force X members and offers them the secret to disabling the bombs in their necks - much to the chagrin of Amanda Waller. He’s also started his own high-end private detective agency - Enigma Investigations, employing both his lovers (Nina and Dierdre didn’t stay away long) and his daughter, as well as circling ex-cop Harvey Bullock for a position on staff. While Batman is hesitant to trust Riddler, he’s become a close ally of Huntress - especially because he was a big fan of her deceased mentor, the Question.
== Notes ==
* Cayden James was a character on the Arrow TV Series.
* Riddler being a foe of Green Arrow is inspired by City Walls.
* Riddler's origin is partially inspired by Matt Reeves' the Batman.
* Helping Task Force X members disable bombs is a nod to Batman: Assault on Arkham.
* His history with Kristin Kringle and Tom Dougherty is from the show Gotham.
* Using the Lazarus Pit to cure his cancer is from Batman: Hush.