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Oswald deserved it. He was a traitor, a liar and a backstabber, so it had been only fair that Edward got around to stabbing him back, although, in retrospect, doing it in front of dozens of people with guards everywhere hadn't been his smartest move.
For the first time in his life, Edward had been truly happy. He had a job worthy of his name, a beautiful girlfriend that truly, honestly, definitely loved him and a best friend who he thought he could count on, something he had desired even before the first two. The ex-Chief of Staff had really thought Penguin had been the one person to understand him, the one he could trust and how did that end? With his entire life being ruined by that little bastard.
Now he had been rotting away in Arkham for almost a year, going through therapies that were better described as torture and medicines that made both feeling and thinking hurt too much, which was still better than the nothingness that filled his core otherwise. Had it been worth it? No. Of course not. It was even worse than the previous time he had been in Arkham, because now he actually had many things he missed, from the power to the faces of the cops forced to obey him to food that actually tasted like food. He missed the expensive clothes Oswald bought him, the feeling of warm water from a hot bath and, above all else, he missed Oswald himself. He missed his smell, the touch of his skin, the softness of his undone hair, the freckles on his body. He longed for that strength, the power, the comfort. The thing he found himself missing the worst was Isabella, almost all of his memories of her had been replaced with Kristen's face and body, the one he had actually fallen for.
The only good thing in that facility was his therapist as she had been the one to help him realize why he killed Penguin, not to avenge his girlfriend, but to avenge the trust he had murdered alondside her on those train tracks. Even if Edward didn't love her, Oswald couldn't have done what he did, more importantly, he shouldn't have lied about it. Not to Edward.
So, yes. Oswald Cobblepot deserved to die. He didn't regret killing him. What he regretted was not having him around anymore and Edward was fully aware that made absolutely no sense.
When the murderer wasn't in 'therapy', Arkham was painfully boring. Everyday felt the same. He woke up, had breakfast, exercised, showered, had lunch, read, worked, read some more and then had dinner before going to sleep, all while being medicated to the point where he felt sick.
While there, he made a couple of colleagues, if you could even call them that. Jonathan Crane was a surprisingly sweet kid at first, and maybe Edward should have started paying attention to him earlier, maybe then he would have saved him from himself and the Scarecrow would never have been born, but the forensic scientist had been so busy sulking in his own misery back then he completely ignored the abuse done to the poor kid. Alas, the boy was broken, Edward was too late.
Even as Scarecrow, he was still the second smartest person in the facility and speaking to him was better than the rambling of the madmen. Eventually, Tetch came into the picture, and while Ed wasn't his biggest fan, Jonathan insisted on keeping him around. The tallest of the trio learned to tolerate him and, for a few months, the three were inseparable, not friends, none of them particularly liked the other, but they could appreciate each other's strengths and so they plotted, planned and schemed together to try and escape. For the first time since Oswald's death, Edward felt truly, honestly accepted. As it was too common in his life, that didn't last long.
The catalyst of Edward's alliance ended up being none other than Gotham's most insane criminal himself, now recently resurrected, Jerome Valeska, the clown himself. He managed to take control of inmates and guards together and forced anyone and everyone to swear loyalty to him or be stomped on before they could be a nuisance. Jonathan and Jervis were smart enough to comply, Ed on the other hand, always the stubborn man that he was, refused to work underneath anyone ever again. He would rather die than lower his head to someone superior ever again. That wasn't what Jerome had wanted to hear, and so, Edward Nygma became Jerome Valeska's newest plaything, all alone in a place close to hell itself.
But Oswald had still deserved it.
It was lunch time that day, after spending minutes in line to get some of the amorphous mass they called food, Edward sat all alone as usual. He poked the blob a few times, a frown on his lips. He felt the seat lower as someone sat by his side, yet he didn't bother turning to face them. He already knew who it was and what they wanted.
"Eddie, buddy! How are ya today?" Jerome laughed, fully knowing the answer to that question. Ed's nose was still broken from the last 'movie night' they had had there. Jerome was a bigger fan of live action performances.
"You know the answer to that question and I would rather spare the saliva."
"Always the charmer, ain't that right boys?" The two burly men standing behind Edward snorted as a response. He was surrounded. "Say, heard ya are getting a new roomie, Ed, you know, since the 'accident' happened to the last one. Bet ya are excited."
The 'accident' was the fate befallen to all of Edward's roommates for being far too unpleasant, some under Jerome's orders, some for just not matching Ed's standards. "Oh, goodie." Edward said with no emotion in his voice.
"Ya know, I heard that this one is REEEAL special, ya should feel honored, Ed."
"I could be roommates with the pope, Jerome, and he would still not be good enough to be my roommate. They can put me in solitary as many times as they want, it won't change a thing. Until they agree to just give me my own room, people will keep on dying. At this point, it's more of their fault than my own." Edward brought some of the blob to his lips.
"You know, I could talk to the higher ups, get them your own room and, once my plan is ready, ya could escape with us. Ya just need to agree to help us. It's not that bad, even your friends did it and they love being on the winning team."
"I don't have friends," Edward turned to Jerome, deadpanning, "and I think I would rather eat my own foot than working for a pathetic unfunny excuse of a comedian like you."
Jerome laughed, "oh, Eddie. You are funny. Hilarious actually! In fact, you quite remind me of my brother!" The clown snapped his fingers and one of his men slammed his head down into his plate. "He is a snob asshole just like you."
The entire cafeteria burst out laughing, except for two men who he once called allies, both of which refused to look at him.
"Make sure to eat all of your meal, Eddie." Jerome whispered into his ear, "ya gotta heal nice and strong, otherwise you won't be as fun to play with anymore and you really don't want to see me bored."
Edward broke his plastic spoon with his thumb and attempted to attack Jerome's face with it. Before he could, however, one of the big men grabbed his wrist, inches away from Jerome's eyes.
"Tsk, tsk, tsk. Wrong move, Eddie. Take care of him boys." They threw him on the floor before proceeding to kick the fallen man. Edward did his best to protect most of his vital items by curling up on the floor. It was no use. Soon his vision faded and he passed out.
By the time he woke up again, he was alone in the cafeteria in a puddle of his own blood. Even the guards hadn't been bothered to take him to the infirmary. With a wince, Edward sat up. His entire body ached, but nothing seemed broken. That was a bonus.
Slowly, he stood up and proceeded to start limping to his room. There was something odd about that exchange, however. Jerome hardly ever cared about his roommates. Why was he so interested in this one all of a sudden? Was he being partnered with someone famous? Maybe he would get their autograph before killing them. Now that was a funny thought.
Edward chuckled to himself as he opened the door of his room. There, standing in the middle of it was a short man about 5'6ft wearing the familiar Arkham uniform. He was pale, which contrasted to his black spiky hair. His nose was long and sharp, the bags under his eyes were pronounced and his freckles were no longer hidden by makeup. He couldn't see it, but Edward knew that, in his pants was a poorly healed leg that gave the man his characteristic look.
Oswald had deserved his fate. It didn't matter if he loved Edward. It didn't matter if Edward had come to realize that, maybe his feelings for the other were deeper than friendship. The Penguin had deserved to die, Edward knew that, so why was he standing in front of Ed now?