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Deal of a Lifetime

Summary:

If someone holds a gun to your head, there are 150 ways you can react. You can take the gun, or you pull out an even bigger one. But not Mike. No, when the gun was pointed at Trevor, he made a deal with New York City’s most notorious crime boss, Harvey Specter.

It started with a drink. It ended in something beyond his wildest expectations.

Notes:

Helloooo, I’m back!
Sorry for the long absence, but work has been insane, and I was on holiday and ended up splitting my free time between three stories coming your way until I got whiplash and decided to focus on this one for now. This was meant to be a oneshot and ended up novel-length – I really didn’t expect this to go where it did when I had the initial idea, but here we are, lol.

Obviously, due to the nature of the AU, the characters do divert from the cannon, some a little, others a lot, and the story deals with darker themes as well; think drugs, gun violence, unaliving people… It absolutely does not go near the level of unhinged I’ve seen in this fandom though (particularly 2019 seemed to have been the year for Gangster fics??) and still mainly focuses on the relationship between Mike and Harvey.

I hope you enjoy it!

Chapter 1: The Deal

Chapter Text

 

“What have you gotten yourself into now, Trevor?” Mike hissed as a bunch of black cars pulled up behind them.

Just one drink, that was all it was supposed to be. A drink, maybe chat up some girls, and see where the night would take them. But no. Nothing could ever just run smoothly with his friend.

Trevor’s face grew visibly more aggravated; the dim light of the streetlights above them reflected in the sweat that started to build on his forehead, and Mike had never seen his eyes widened this much. It was a miracle his eyes didn’t just plop right out.

“I-It’s nothing! But maybe, we should, you know…” Trevor stuttered. The door of the first car opened, and two large men dressed completely in black stepped out. Mike could clearly see the guns stored in the holsters around their hips.

“Run for our lives?” Mike managed to bring out, barely catching the soft “yeah,” Trevor let out for he was already running.

He hated running.

As much as he loved his bike and thought he was in decent condition, it also meant he rarely had to walk, let alone run anywhere; he noticed quickly the ache in his knees and the painful burn in his lungs as he just sprinted away. He didn’t even dare to look back to see if they were being followed.

Any faint hope he had that whoever they were, they weren’t after them, vanished when the screeching of tires echoed through the late evening. The adrenaline spiked up in his body unlike anything he had ever experienced - he just kept running, taking sharp turns at every opportunity, trying to summon a map of New York in his brain to keep track of where he was. It was no use, his brain shut down, too focused on just keeping his body moving.

“Yo, over here!” Trevor shouted, and Mike followed him into a small alleyway without hesitations. They got about two hundred yards in before hitting a snag at the end of it, closed off by a fence at least twice his size. Not good.

“Shit shit shit…” Trevor let out, throwing himself against the fence, trying to climb it. Not knowing what else to do, Mike tried to boost him up. Whoever they were, if they wanted Trevor – and he was pretty sure he himself didn’t do anything recently that would have warranted armed men to be chasing him through the city – maybe they would back off when they realized he had escaped.

A shaky plan, at best.

The bright headlights of a car ahead of them suddenly blinded Mike; he shielded his eyes instinctively, somewhat aware of Trevor crashing to the ground next to him. He turned away, just for more light to burn into his eyes – there were cars on both sides of the fence.

They were officially screwed.

“What did you do? Who are they?!” Mike asked, whisper-yelling as quietly as he could, still trying to catch his breath. God, he needed to go running more often.

“I… I…” Trevor mumbled, still on his knees, exceptionally useless, more so than usual.

The doors of the car on their side of the fence opened, and three men got out. The two from earlier, and then someone else. Someone just as tall, dressed in a suit that even in the darkness seemed expensive. He had a stoic expression on his square face, shadows casting down from his cheekbones, making his jawline look impossibly sharp.

It was impossible to look away. Impossible to move. Mike had to actively remind himself to breathe, if just not to faint in front of the strangely attractive pursuer.

“Gentlemen,” the man said, his voice low and calm, completely in control, “I hope you enjoyed your evening exercise. Now, let’s not make this any more difficult than it needs to be”

A shiver went through Mike’s body. This was how he was going to die, next to Trevor for doing lord knows what. Just his fucking luck.

“Mr Specter,” Trevor said, slowly standing up, his hands lifted in the air next to his shoulders. “You didn’t need to go through all the trouble of coming out here…”

“Apparently I did,” the man cut him off.

Specter. Where had he heard that before?

“Where is my money, Trevor?” Specter continued, a clear edge in his voice that wasn’t there before. He took another threatening step forward and Trevor crumbled right in front of him, sheer terror on his face as he bowed his head submissively. Mike had never seen him like this before.

“What’s going on? What money?” Mike asked before he could stop himself. Suddenly, Specter’s eyes were on him, filled with an intensity that pierced through him like daggers, sending a shiver down his spine.

“And who are you then? His boyfriend?” Specter asked, a little smile playing along his lips. He was playing a game with him, of course he was.

“I can do better than him,” Mike said, mentally slapping himself. What the fuck was wrong with him? But Specter huffed, by some miracle he even seemed amused by his remark, his eyes gliding down Mike’s body. He suddenly had the urge to stand as still as a statue, to not give him any reason at all to perceive him as a threat.

Just an inconsequential bystander, nothing more.

“Your not-boyfriend borrowed a substantial sum from my organization a few weeks ago. Deadline for payback has past, and nothing. No explanation, no apologies, no amends.”

“I am going to get it to you, I swear! There just have been some complications and…”

“Shut up,” Specter shouted suddenly, freezing the blood in Mike’s veins with the sudden change of his demeanor, the way he glared down at Trevor like he was nothing. And then, as if nothing had happened, he turned back to Mike with that little smile again.

Mike swallowed hard, resisting the urge to take a step back.

“Come on, Harvey, let’s just finish them. Not worth our time,” a voice behind him suddenly said. Mike whipped around, seeing another man in a suit leaning against the fence from the other side. He looked older, his face rounder.

And then it clicked in Mike’s brain.

Harvey Specter. Infamous leader of New York City’s underworld. He was like a phantom; the papers wrote about him and his gang, the things they did, and yet there weren’t any pictures of him, no one who would describe his face. Or could.

He had never been caught, at least not in a way that ever leaked to the outside. Granted, Mike wasn’t all caught up on the matter, nor did he care for the details, but he had seen that name often enough to know one thing: This guy was not to be messed with.  

How could Trevor have been so stupid and borrowed from the crime boss in the city?! Why would he get involved with him?!

“Patience, Louis,” Harvey said calmly, seemingly not bothered at all. He enjoyed this, Mike realized, enjoyed the power he held at that moment, enjoyed how Trevor cowered in front of him.

Wait a second.

No one had ever seen his face or lived to tell the tale, but Mike just did. And Harvey had seen his. He had found him before, there was no way he wouldn’t do it again. Even if he could escape, they were completely surrounded, he’d be shot dead before he could even make a move.

They were both dead men. Even if by some miracle Trevor had the funds somehow, he had no reason to keep them alive.

Mike willed the panic down, willed his brain to think, to find a solution. What to do when someone holds a gun to your head?

Harvey’s attention returned to Trevor, staring him down, signaling over his shoulder for one of the henchmen to step closer, who approached immediately, cocking his gun already. And Mike’s brain officially stopped working.

“Wait!” he blurted out against all of his better judgment, “If Trevor owes you money, what if I work it off for him?”

Harvey signaled the man to stop, and for a moment, Mike felt relieved. At least he had bought them some time. He felt Trevor’s eyes on him, but it was unimportant; all that mattered was the gaze from Harvey, straight into his soul, his eyes that lit up with something, the amused smile back on his face.

“And what could you possibly do for me?”

“Anything,” Mike said a little too quickly, and Harvey cocked an eyebrow, the glint in his eye only growing.

“I mean, I am great with numbers,” Mike continued, trying to maintain his composure. “And the law. I’ve passed the bar”

A round of laughter went through the strangers that Mike really couldn’t place, but whatever confidence had possessed him to offer this in the first place, it vanished.

Harvey smiled too, but it wasn’t nearly as condescending as the laughter sounded, so Mike just held onto his gaze, praying he would make it out alive.

“You’re assuming that I need a lawyer because I get caught, which I don’t. And even then, I have access to lawyers. The best there are,” Harvey explained calmly. He didn’t sound entirely put off though, intrigued even, albeit still amused. And annoyingly, he made a damn good point.

Think….

“Yes,” Mike scrambled, “but I can help you not break any laws in the first place, or at least create scatter evidende and create enough doubt that no jury would ever put you behind bars. Why rely on some lawyers if you can just exist in the gray instead?”

Now Harvey smirked. “I like the gray.”

Mike hadn’t realized how he had held his breath until it escaped slowly. He felt himself relax a little. Whatever happened just had to happen now.

“Thought you might,” he said, even allowing himself a little smile, never backing down from Harvey’s intense eyes that still lingered on him.

“He’s a genius! He’s good with everything!” Trevor suddenly said, jumping on the lifeline. Mike had half a mind to kill him himself.

“Shut up, Trevor,” Mike said immediately. He did not sacrifice himself for him to ruin it by saying or promising anything – this was Mike’s life. He needed to be in control of the deal.

“I’m curious,” Harvey said, “What about him makes you think he is worth saving?”

Mike opened his mouth to answer the question, but nothing came out. He didn’t know if Harvey would really want the truth, if he would mock him for it. But somehow, Mike believed that he was genuinely curious – and he had literally nothing left to lose.

“He’s my friend,” he finally said. Harvey huffed.

“You need better friends”

“Hard to argue with that right now,” Mike mumbled, looking at the wreck that was Trevor next to him. If even a criminal like Harvey Specter thought he could do better, then he really needed to sit down and reassess his life. If he still had one.

“What’s your name?” Harvey asked.

“Mike. Mike Ross.”

“Well, Mike Ross. We have a deal”

“Oh come on, seriously?” the other guy, Louis, exclaimed, clearly annoyed.

“You got a problem with that?” Harvey barked back, his face hard and authoritative again. Louis backed off immediately, away from the fence.

“None whatsoever,” Louis said, his voice cold as ice.

“Good”

The smirk reappeared on Harvey’s face before he made a weird movement with his hand and everyone around was moving back to the cars, except for himself and Mike who didn’t dare to move a muscle.

“After you,” Harvey prompted, pointing to the car with his hand, his voice oddly charming all of the sudden. Hesitantly, Mike gave Trevor a last look and slowly moved to the car, Harvey right behind him.

Only when he was sitting on the backbench, the adrenaline slowly subsided, and his brain cleared up again he realized what just happened.

He had made a deal with Harvey Specter, the head of the most notorious criminal gang in the city. And now he was in a car with him and his henchmen, at his service.

What the fuck had he gotten himself into?!

He sat silently, not daring to ask any questions, not even daring to look out of the window so as not to give the impression that he was mapping where they were going. He didn’t think there was much point anyway. Wherever they went, he had a feeling he wouldn’t be able to escape anyway.

The other men were silent too, but he could feel Harvey’s eyes still on him. He wondered what he had seen in him that made him agree that he would be a useful resource.

But Mike was a man of his word. The fact that his life was in shambles and he didn’t have anything to go back to aside from his crappy apartment and his crappy job as a bike messenger helped too.

The only person who still mattered was Grammy. He’d protect her at all costs. But as long as Harvey didn’t go after his grandma, and literally why would he, Mike knew he would follow through with this.

He only wished he knew what exactly he just signed up for. But no one seemed to care to fill him in.

He didn’t even know how long they had been driving when Harvey finally spoke.

“Was he right? Are you a genius?”

“Compared to Trevor? Sure. I would have known better than to borrow money from you,” Mike mumbled. Sass had gotten him this far, he felt like he couldn’t just submit now or else Harvey might change his mind.

“So you know who I am then,” Harvey grinned, sounding oddly pleased with himself.

“I like to read. Your name’s come up.”

“I bet it has. You must have read all the worst things about me, which makes me wonder… does volunteering your services make you brave, or does it just make you stupid? What do you think?”

Mike swallowed hard, feeling his palms sweating up while simultaneously growing cold. Holding on to his completely unjustified confidence, he dared to look at Harvey once more.  

“I don’t know yet. But let me know when you have figured it out,” he said, hoping he sounded calm and cool rather than as nervous and on edge as he was feeling.

Harvey smirked once again, tilting his head slightly. “If you died tonight, who would miss you?”

Mike didn’t know if it was a threat or not, but it didn’t matter; his heart started beating impossibly fast in his chest, so loud he was sure Harvey could hear it too, feel it even.

“Are you trying to decide whether it’s worth the hassle?” Mike asked back, clenching his hands into fists.

“Leave the questions to me, lippy. You got anyone? Nosy roommates, girlfriend… boyfriend?”

Harvey’s voice was a little higher as he said the last one, his eyes gliding up and down Mike’s body just as he had done earlier, making him shiver again. He couldn’t possibly place what it meant.

“No. Nothing of the sort. Pretty sure my landlady would notice if I don’t pay her rent on time though, so you’d have about a week to cover it up before they start looking for me.”

And his Grammy. But Harvey didn’t need to know about her. He’d rather Harvey thought of him as a pathetic loner than draw his focus to the old woman who he might consider a loose end. Mike had no idea how far Harvey was willing to go; sure, he didn’t kill Trevor, but that didn’t mean much.

“So you’re a loser,” Harvey said matter-of-factly. There was no bite in it, it didn’t even sound judgmental, even if the guys in front started chuckling.  

“I guess so,” Mike muttered.

“That’s good. Means I can help you find a new perspective,” Harvey said, and somehow, it sounded reassuring. Even if Mike was sure any perspective Harvey could offer wasn’t all that desirable to him.  

Mike didn’t find the words to reply. He should be grateful that Harvey didn’t kill him – he probably recruited people like him all the time, desperate people who are willing to do his dirty work.

Except that this was only temporary, of course. Hopefully. Would he be able to leave when the debt was settled?

“Out of curiosity… How much does Trevor owe you?” Mike asked, glancing at Harvey again.

“Two million dollars, give or take.”

Mike’s heart sank. Two million dollars. Temporary started to feel a lot longer than he had hoped for.  But that was on him for not knowing all the details before entering into a deal. So he forced himself to nod.

“Okay. Well, we should probably figure out the details of this… arrangement,” Mike started. He knew this, he knew the law, he had a lot of (very theoretical) knowledge of contract negotiations. He could do it. “Worth of labor, working hours, expectations…”

“We will,” Harvey interrupted, still amused rather than annoyed. “All in due time. First, I need to find out more about you and how useful you will be to me, then we can talk numbers”

Mike nodded again. He really didn’t have a good negotiating position, in a car with three people who wouldn’t hesitate to kill him, going to an unknown location.

All of this was insanity. But he had committed now, and there was no going back – he sure as hell was about to find out what he had got himself mixed up in.

All he had was the amusement that was still in Harvey’s eyes, and he held onto it. Whatever he saw in him, whatever entertained him, it was what had kept Mike alive so far. He had to make it last.