Chapter Text
Oswald had just wrapped up a meeting with a fellow mob boss when the green clad stranger entered the lounge.
Through the open-curtain entrance he carried himself with a peculiar gait, hands behind his back and chin up. He froze for an instant, head swiveling mechanically as he scanned the semi-crowded room.
In the lighting he could make out the man's outfit; hideous green pants, a button-up with its sleeves rolled-up and a bulletproof vest, proudly worn over like a lion wears its mane. Around the mans neck was a dogtag.
After surveying the room, his gaze fixed on Oswald, and he felt himself try to compact, make himself smaller, but any attempt failed as the man smirked and strode over to his corner booth.
As he approached, he appeared to bounce with each step, and which each of those steps a clump grew in Oswalds throat. Then, they reached the table.
Now, standing a mere few feet from The Penguin himself, the audacious stranger took it upon himself to slip into the opposite side of the booth from Ozzie.
He smiled, lips sealed and Oswald finished his analysis by picking up on the man's brown skin and a particularly odd shaped chin.
Oz huffed, pulling his cigarette extender from his lips and blowing a cloud before beginning. He glared at the man across the table, daggers thoroughly stared.
And at this, the man's smile seemed to grow three sizes. He laid both hands on the table's surface, caressing the wood. Then he spoke.
‘Nice place you got here.’ his voice was crisp, words like butter on his tongue. ‘Did you do the decor yourself?’
‘Out with it.’ He heard his own gravelly tone, sandpaper to an already tense atmosphere.
The man tilted his head, readjusting his glasses. ‘I'm sorry?’ he asked, letting a sly smile cross his face.
‘What do you want?’
He perked up, hands flying to his lap. He then spoke.
‘I come in all sizes - some major, some compact; you get what you seek, you give what you owe back;’
He then leaned across the table inches from Oswalds nose.
‘what am I?’
Shit.
He'd heard about this guy in the papers, some maniac who kidnapped the mayor's daughter and held a gameshow for her release. He'd read it and scoffed—just another lunatic—but now that the perpetrator was across the table, he felt the slightest inclination to run away screaming.
But he stood his ground, hoping he didn't appear too freaked out. He took another drag from his cigarette.
‘A riddle, is it? Really living up to your street name, eh?’
The man—The Riddler—frowned, ‘Yes, I suppose. The Gotham Times has a tendency towards the overdramatic.’
‘And you don't class yourself among their bracket?’
‘Certainly not Mr. Cobblepot, I just like a certain flair in my work—makes it stick in one's mind.’
Oswald frowned, ‘And your work is… what, terrorism?’
The Riddlers eyes narrowed in on him. ‘You're avoiding my question, Oswald.’
A shiver ran along his shoulders and he hoped to god it appeared faint.
He bluffed, ‘I'm one bad glare away from sendin’ you out, you know that right? Dragged by your tailored green coat tails and thrown on the pavement.’
Riddler smiled, and began fiddling with the lamp that was sitting on the table. Oswald had in fact decorated this place himself, right down to the floor they all stood on, and that lamp had been the result of countless decisions and backtracks. This man dared walk into his establishment and play with his belongings; he'd better have reason.
Then the Riddler spoke again, words passing from his lips in idle fancy.
‘You know, I don't have much family, right? My mom and pop passed a while back and I never really knew my grandparents,’
He looked Oswald in the eyes.
‘but when I talked with Gertrud I think I finally understood what that connection feels like, you know?’
His mother. He wouldn't let him do this—he couldn't. How on earth had this psychopath located his mother?
‘Now you listen here-’
‘No.’ The Riddler grew dark, eyebrows furrowed. ‘First, you answer my riddle. Then, I'll leave your old lady be.’
He by all rights should have grabbed this menace by the scruff of his neck and pounded his face into thick red pulp… but he allocated a moment of thought. Thinking it through, he calmed down, leaning back against in the booth.
He sighed, ‘...what was it again? Somethin’ about comin’ in different sizes and owin’ somethin’, right?’
Riddler's presence softened, now smiling. ‘Yes, I can repeat if you wis-’
‘Nope, no worries. All good.’ If he heard another rhyme out of this guy's mouth he was gonna go ballistic.
He looked inwards, drumming the table with his fingers as he raced through possibilities. Money? Nope, too vague. A dept? Maybe… but what would him or Riddler owe each other?
It then struck him, and the dawning realisation must have been plastered on his face as the man across the booth grinned ear to ear.
‘A favour.’ He breathed it out like he'd been deprived of talk, breaking his silence and letting himself feel semi-accomplished.
‘Very well done,’ he clasped his hands together, ‘few appreciate the art of a good question.’
Oz nodded, feigning understanding. A favor… he thought, this'll be good.
‘Now.’ Riddler began, placing his palms flat on the table, face cast in dim light from the green glowing lamp. His eyes were stark black, pupils like vast cavities.
‘I'm asking you—as a friend—’ he smiled mockingly, ‘to fulfil an itty bitty little favour; one which I will pay back in due time!’
His tone reminded Oswald of a infomercial he'd seen a few days back, where the man on the television was trying, very earnestly, to sell him blackout shower curtains. He admired his bravado, but he'd need to be a bit more specific.
‘Go on,’ he uttered, gesturing for him to continue while taking an absentminded sip of his now-cold lemon tea.
The Riddler nodded, checking over his shoulder into the booths behind him and around. Finally he looked back to Oswald, his smile tapered but not gone.
‘I want you to kill James Gordon.’
He spat out his tea; whether through surprise or hilarity he himself didn't know, but the effect was still felt.
‘Oh dear, sorry,’ he fetched a handkerchief from his breast pocket, wiping up the wet splodges on the table before handing it to Riddler who now sat dazed with an unpleasant frown on his face.
The frown struck him as particularly unnerving, it seeming in contrast with the man's entire being.
‘I am truly sorry,’ he finalised his apology, looking Riddler in the eyes, ‘you are joking, right? It is a joke?’
The look of annoyance on The Riddler's face made his intentions clear. The shorter man felt himself sink into his seat.
‘Oh. Right. Excuse me,’ he ushered a waiter over, ‘can you bring me and my associate the strongest gin we have?’
The waiter left and Riddler scoffed, ‘I knew it would be difficult, but I thought you would at least-’
‘Difficult?’ Ozwald felt his eyes nearly bulge, ‘You're asking me to kill the police Commissioner, I'd bloody well hope it'd be difficult.’
‘It will be,’ Riddler began, ‘I never said it wouldn't be! I was asking for your help in return for a favour, one which could prove very valuable to you!’
‘And what could you give me?’ The waiter came back, laying a large bottle of gin and two shot glasses on the table before vacating. Oswald forsake the glasses, instead pouring it directly into his mug.
Riddler breathed in, clearly preparing some monologue that Oswald was all too clear-headed to endure. He took a swig from his mug as the other man started.
‘As of recent, I've found myself employed within the Gotham City Police Department as a private detective. I don't care for the position itself—god forbid I help those fools—but it's given me some leverage I doubt many other costume criminals have.
‘The police never suspect me of anything, never question my motives or what I do in my spare time, and any that do…’ he smiled, ‘well let's just say I have adequate backgrounds on all employees. Those on the force usually have skeletons they'd rather keep closeted.
‘However,’ he said with spite, ‘in the past while, I've become personally engrossed in this whole Batman nonsense. I'm sure you know.’
He'd said Batman in airquotes, and Oswald nodded in understanding. The bat had interrupted a drug operation he'd carried out a few months ago, rounded up all of his lackeys and laid them right out for the police. He'd lost thousands, all of it due to some high and mighty masked vigilante.
‘Well,’ Riddler piped up again, ‘I've set up various schemes trying to catch him, kill him, the sort. None have worked so far and still the man proves elusive. Then, earlier this morning, Commissioner Gordon rocks up to my private office and claims that I'm “abusing my power as a member of the police force” in order to catch him or some jargon I can't bring myself to remember, saying he'll boot me out or put me in Arkham.
‘I suspect he's onto me, and I want him gone. You know how fixated he is on cleansing the city of our kind, and I think we'd all benefit from Gordo taking a long walk off a short pier.’
Silence fell across the table as Oswald searched inward, churning over Riddlers words in his mind. He was right; he knew that. If he had a nickel for everytime he'd wanted to see Gordon's head on the chopping block he'd be a regular Wayne, and having him gone would certainly make criminal living in Gotham much easier.
He looked for a reason not to, and only found a long list of why to's. ‘You know what, sure.’
The green clad man made a sigh of relief, taking the glass and pouring himself a shot.
‘However,’ he spoke up again, ‘I do hope you have a real plan for this, not just “kidnap him and make him play Russian Roulette with himself on GNN” or whatever nonsense you usually do.’
Riddler shot a hand to his heart, mimicking a sting, but a sly smile still crept out, ‘How you wound me! But you're right, and I do have something planned; not my usual shindig, but I hope you'll find it equally painful and deserving for our little Commissioner.’
As The Riddler took his shot, Oswald spotted a familiar glint in the man's eyes, one he usually only saw in those of great value. He saw purpose in this man, something many residents of Gotham lacked.
‘So I help you,’ Oswald began, ‘lend you some of my men, some of my money, till Gordons good and buried, right? What could you offer me?’
The Riddler paused, staring up at the ceiling, and it occurred to Oz that the man likely hadn't planned to get this far.
Finally, he jolted back into talk, ‘I'll be your personal mole, free of charge; how's that?’
Oswald imagined it, and he could see the value in having a GCPD mole he didn't have to pay a C-note a month to, especially one with an intellect as vast as Riddlers.
‘Fairs fair. We got a deal.’
He reached out a black-gloved hand and Riddler shot his purple one back, meeting in a firm shake. ‘Pleasure doing business with you, Mr. Cobblepot.’
‘Please,’ the shorter man insisted, withdrawing his hand, ‘call me Oz.’
Riddler raised an eyebrow, then let it relax. ‘Then you can call me Edward.’
In this brief moment of silence following this, Oswalds attention was drawn to the staged singer at the other end of the lounge; her tones not honeyed, but honest. He insisted on private auditions between himself and all acts that performed here, and during hers he nearly wept at how forward and directed her lyrics felt.
That's what he loved about Gotham; it could belong to anybody, you just had to seize it by its roots and give it new soil. The man on the other side of his table was attempting to repot the city, and he'd ensure care was taken in its gentle, bloody planting.