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Brainwave - What if Ryan used to work undercover trying to expose a drug ring?

Oh, the possibilities... It could come up in a current case.. Or perhaps an AU where Esposito first meets Ryan while undercover.. Ooh, or someone could recognize him and he starts getting shot at.. Seriously, just take the concept and run with it guys.

Ship, or shipless, it's up to you! I'll take what I can get!

Undercover!Vice!Ryan (Part 1)

Dead bodies were not part of the plan.

Kevin Ryan crouched down next to the body, doing a quick analysis, two bullet holes, one to the head, one to the heart. 38, he guessed, quick and professional, which told him nothing about which one of Franklin Tempest’s enforcers had done the deed. It was both a boon and a disaster. The corpse, Louie Jamison, had been part of Tempest’s inner circle. He’d been in Kevin’s way, preventing him from gaining access to the circle because Kevin was working as his right hand, but also had given him access to quite a lot of information vice needed to pull down the entire drug ring.

He zipped his ragged jacket a little tighter and stood, heading up the alley. He’d have to play this careful, he thought to himself, already plotting out his next four moves. He needed to call his handler, warn her he’d be off grid for a few days while he secured the position. Also make sure his alibi was tight, he realized, so he decided to swing around to a Russian flop house, make sure Kayla, a long undercover vice detective who was looking to bring down a ring of human traffickers, had the evening free.

Kayla had been a blessing, their undercover social circles overlapping. Kevin O’Malley, his undercover ID, had become her best “client” and helped him maintain a certain appearances that had endeared him to Louie. It also had helped keep them both sane, having a few hours a week where they got to be themselves.

Things went well the next morning at Tempest’s loft, having handled the money drop for the day personally. He’d shrugged off his presence, telling Tempest that just because Louie hadn’t showed up, holed up with some girl probably, that didn’t mean his business wasn’t gonna get taken care of. Tempest had been pretty impressed.

He was feeling pretty confident until he turned the corner, a big bruiser stepping in his way and flashing a badge. “I was having such a nice day,” he complained, checking out the guy. Good looks were ruined by the no nonsense glare, add in a bit of a military ramrod posture, and the suit… detective, Kevin decided. Homicide, he guessed.

“How can I help you, officer?” he asked insolently, flashing a grin.

“Detective Esposito,” the man corrected him, and Kevin bit back a grin, already figuring out how to play the guy. “I have some questions for you, Mr. O’Malley.”

“Oh, might have an answer or two for you, Officer,” Kevin replied, surprised when his flip response didn’t provoke quite the frustration level response he’d predicted. “You want ‘em now?”

“You know a man named Louis Jamison?” he asked, and Kevin nodded.

“Sure, I know Louie. He get in another bar fight? Cuz I ain’t bailing his ass out again,” Kevin replied.

“Your friend was found shot last night,” Esposito told him, and Kevin stopped, forcing himself to look shocked.

“Shot? Shit, really?”

“You telling me you just came from Tempest’s loft and no one told you?” Esposito pressed, and Kevin went for blank.

“Who? I just dropped by to see a friend on 12th, Pierce Connors,” Kevin lied easily, knowing exactly what any runner from Tempest’s group in this position was supposed to say.

“Just for laughs, where were you last night?” Esposito asked, and Kevin shrugged.

“In bed,” he answered, flippant again. Esposito just raised an eyebrow, waiting expectantly. “Picked up some company on my way there, around 10. You want her number, or is your ‘just for laughs’ not up to checking alibis just yet, Detective?”

Esposito stared at him for a long moment, then pulled a card from his wallet. “Look, you hear anything, decide you wanna help your friend get some justice, give me a call.”

“Yeah, sure,” Kevin replied, a little rattled as he shoved the card into his jeans. The detective seemed to have a little insight past his carefully projected exterior to make that overture, he guessed, turning up an alley, making a note to ask his handler to check out Javier Esposito when he checked in a few days later.

Undercover!Vice!Ryan (Part 2)

He wasn’t surprised that a few hours after Tempest officially had him installed in Louie’s position, a squad car pulled up alongside him on the street and Detective Esposito stepped out. He offered up a big grin, mentally cursing that he hadn’t had time to call his handler since their last encounter. “You just live to ruin my good moods, Detective,” he greeted the man, wondering if it was time to take a new tactic with the man.

“Want to ask you some questions down at the station,” Esposito replied, and Kevin offered up his wrists dramatically.

“Okay, take me away, Officer,” Kevin replied cheerfully. “You wanna cuff me? ‘Cuz I might be up for that.”

That got an actual quirk of a grin, so Kevin marked flirting off his list of ways to ruffle the detective, a little sad given that the other man was nice to look at. It usually worked with the military types, but it seemed Esposito wasn’t among the usual caliber of ex-military cops. Hit ‘em hard and low then, he decided, once Esposito got back in the car.

“Did you see the Red Sox kick Yankee ass last night?” he asked enthusiastically. “Man, that was an awesome game.” Yup, he grinned, seeing Esposito grip the wheel a little tighter. Never failed to piss off New Yorkers, himself excluded. He continued to rattle off stats and less than complimentary observations about the Yankees as they drove, wondering if maybe it was a good thing he was in the backseat and out of reach.

He was being lead by a uniform officer to an interrogation room when he overheard Esposito mumble to a pretty brunette woman, “Punk would not shut up about the Red Sox the whole ride over.”

“Aww, Esposito, you want me to take first crack at him, before he insults your precious team anymore?” she teased him, and Kevin had to hide a grin. He liked the woman automatically.

He grimaced when he caught his reflection in the mirror, raking a hand through his grimy, too long hair, reminding himself that in just a week or two, he’d have enough that vice could pull him out. If he didn’t get held up too long on the murder rap, he mused, knowing that could scare Tempest off fast.

To his surprise, both the female detective and Esposito entered the room. “Detective Kate Beckett,” she introduced herself, and Kevin wiped his hand on his jeans before offering it to her. She looked at it with a bit of disdainful amusement, but ignored it as she sat at the table. “I hear you’re a Red Sox fan,” she remarked idly, and Kevin pegged her as ‘good cop’ quickly.

“Yeah, your boy Esposito here seems to be pretty solidly stuck in Yankee territory, but how ‘bout you, Detective?” he asked, and she grinned.

“Oh, you know us girls, I pick based on the prettier uniforms,” she replied, and Kevin forced a grin. She was good, he mused.

“A Red Sox fan then,” he quipped. “How can I help you, Detective?”

“Where were you three nights ago, around 11pm?”

“This about Louie?” Kevin asked, tilting his head. “I already told your partner, I was with a girl. Kayla. One of the Ukrainian girls, you can usually find her at a flop off 19th.”

“Interesting, because we’ve got your prints on the case Mr. Jamison was carrying,” Esposito broke in, and Kevin shrugged.

“Probably because I worked with the guy,” Kevin replied easily. “I’ve handled his briefcase dozens of times.”

“Pretty convenient that word on the street has it that you’re no longer playing second fiddle to Jamison. Stepped up into the big man’s shoes.” Esposito continued, turning his glare up.

Undercover!Vice!Ryan (Part 3)

“And if you had proof of that, I wouldn’t be sitting here, free to walk out at any time,” Kevin replied, leaning back in his chair and lacing his fingers behind his head. It couldn’t hurt him to point them in the right direction though. “You’re rattling the tree, but nothing’s falling out. Hypothetically, let’s say I may have heard it was a pro hit. So all the alibis in the world don’t do shit for me. But here’s the thing. Rumor has it whoever stepped into Louie’s shoes would be inheriting a mess from some bad dealings he had with Bryan Kelly, if you catch me. Hypothetically, and all.”

“You’re saying,” Beckett grimaced slightly as she played along, “hypothetically of course, that we should be looking at Kelly? Why should we believe you?”

“If, hypothetically,” Kevin was enjoying the way saying hypothetically was making Esposito roll his eyes. “I was the one who had inherited Louie’s business, and hypothetically inherited the mess with Kelly, maybe I’d want someone breathing down his neck, give me time to get my feet under me solid.”

“You’re a real piece of work, you know that?” Esposito grumbled, making a note.

“Aww, I think you’re pretty cute for a Yankees fan too, Detective,” Kevin replied, falling back on flirting, which definitely made Beckett smirk. “You ever wanna catch a game together, you seem pretty good at finding me,” he added.

“Okay, thanks, Mr. O’Malley,” Beckett put in quickly, seeing Esposito fold his arms. “We’ll be checking on your alibi and information. Don’t leave town, we may want to speak to you again.”

“I’ll look forward to that,” he quipped in Esposito’s direction, rising and heading out. He made it out to the street, deciding he needed to find a quiet place to make a call on his second burn phone and get his handler to make sure the investigation got held up a little if it swung back around to him. He was too close for this to get sour.


“Heard the cops hauled you in, O’Malley,” Tempest puffed cigarette smoke, almost to a comic effect as he spoke.

“They’re running in circles,” Kevin replied, sounding bored. “Minute I told them I had an alibi, they start sniffing around Travers. Then it’s Kelly. Then I got bored.”

Tempest chuckled, amused. “Heard you walked out mid-questioning.”

“Like I said, they got nothing. Wasn’t worth hanging around once I was sure of it,” Kevin explained, and Tempest nodded.

“You got a good head on your shoulders,” Tempest praised him. “It’s why I want you with Travers tomorrow night.”

Kevin listened carefully, all the while doing a happy dance on the inside. He had everything he needed to feed his handler, and the ring was going to come crashing down. Best of all, he had Tempest outlining the whole thing. “One more thing,” Tempest said, as he stood to go. “Make sure you got a solid for tonight. That cop, Esposito, is getting to close to Kelly. Kelly ain’t got your head for throwing him off, made too many slips. I got a guy taking care of it, but I don’t want it coming back on our new wunderkind.”

“Got it,” Kevin replied, brain scrambling for a way to cover his bases.

Undercover!Vice!Ryan (Part 4)


“Lim, you gotta do something,” Kevin hissed.

“Look, how do you suggest I tip off the guy without dropping your investigation?” she hissed back through the phone. “Tempest will know it was you if we send people to arrest the guy or put someone on Esposito. Then the whole operation is a wash, no drop tomorrow, no drug ring on a platter.”

“What if the guy Tempest sends screws up?” Kevin suggested. “Gets himself shot, maybe. Didn’t realize the partner was coming over for dinner. Whatever it takes, Lim.”

“You’re gonna risk this going south,” she warned him, but he knew she was going to do it.

“Look, Esposito’s sharp, and Tempest is an idiot to send one guy,” Kevin retorted. “As long as you make sure it gets out that way, no one will look too hard, not till it’s too late.”

“All right,” she said finally. “You wanna run it this way, we will. You be ready for fast extraction if it goes wrong, you hear me? It’s great you want this guy warned, but if you’re not reading it like you think, you’ll be dead instead.”

“Careful, you’re sounding concerned,” Kevin chuckled, hanging up and tucking the burn phone back into the fake panel in his kitchen. He sighed heavily, waiting for his pounding heart to settle again. Time to go set himself up with an alibi, then wait for everything to drop into place.


Vice had borrowed a few homicide detectives, Kevin noted as he was cuffed, trying hard not to grin like an idiot as Esposito cuffed him and began patting him down. “You still looking for that murder confession, Detective?” he couldn’t resist getting in a last barb while he could. “Front pocket.”

What was actually in his front pocket was a directive from Vice and his ID, his get out of jail ticket Lim had insisted he would need to have on him. “Yeah, right there,” he suggestively teased the detective as he reached into Kevin’s pocket.

“Son of a bitch,” he heard the detective curse, sounding half amazed.

“You’ve been a good sport, Detective, don’t spoil it by punching me now,” he joked as Esposito turned him around roughly so he could look him in the face.

“Where’s your handler?” Esposito demanded quietly. “You shouldn’t be down here without backup.”

“Right here, detective,” Lim flashed a badge at him, nodding to the cuffs. “Sorry, Kev, I got held up confirming Tempest is in custody. We’re good, got all the players.”

“Hey, who’s good?” Kevin insisted, grinning once Esposito had the cuffs unlocked. “Thanks, man. Officer Kevin Ryan, by the way.”

“Nice to meet you,” Esposito replied, shaking his head. “Even if you’re a Red Sox fan,” he added, and Kevin laughed.

“Man, can’t believe you fell for that, Yankees all the way,” he brushed it off, accepting his ID back, and the clean jacket Lim offered him. “Glad to see you alive, though,” he added, before turning and following Lim up to check in.

Several hours later, showered, in his own clothes and only in need of a haircut to get back to himself, Kevin was back at his desk, eyes starting to blur as he worked on his reports. He barely looked up when someone dropped into the chair, then did a quick double take when he realized it was Esposito. “Hey, what’s up?” Kevin asked, rubbing at his eyes.

“Realized I forgot to say thank you,” Esposito replied. “Lim told us you took a pretty big risk to make sure I had warning that Tempest sent a goon after me.”

“Hey, you’re the first New Yorker I’ve ever seen not crack when I do my crazy Red Sox fan imitation,” Kevin deflected easily. “Anyone that cool I gotta keep an eye out for.”

“Not to mention the flirting,” Esposito remarked wryly.

“You just don’t crack, do you?” Kevin complained. “Any other cop would have lost it, gotten me my ticket out the door.”

“Nope,” Esposito replied, grinning. “You’re a pretty cool customer yourself.”

“Anyway, glad you’re okay,” Kevin managed, stifling a yawn. “Look, I should probably finish up.”

“It’ll keep,” Esposito replied, standing up. “Come on, I’ll buy you a drink.”

“Uh, I don’t…” Kevin started to protest but looking up at Esposito, his resolve wavered. “All right, one drink.”

Re: Undercover!Vice!Ryan (Part 4)

Re: Undercover!Vice!Ryan (Part 4)


Holy crap! I love it! I love the lingo, the way the whole thing flowed perfectly.. and Ryan! Just so damn competent, but managing to poke some fun at the same time. And- and- the plot, too! I was expecting some short little thing, and here I won the lottery and got a plotty, lengthy, exciting one!

Thank you so, so much for writing! <3

Re: Undercover!Vice!Ryan (Part 4)

Loved this! Very well done.

Re: Undercover!Vice!Ryan (Part 4)

Hello! OP here again!

I don't know if you'll ever stop by here again, but if you do, I just wanted to let you know that I've reread this story about seven times since you've written it. It's my go-to story when I'm in the mood for Ryan gen fic - heck, my go-to story for Ryan-fic at all!

I love it so so much, and wanted to thank you again for writing it! You definitely deserve it, considering how many times I've read it through. :)

Re: Undercover!Vice!Ryan (Part 4)

This. Was. Amazing. I'm sorry it took me so long to find!

Re: Undercover!Vice!Ryan (Part 1)

Wunderbar. Just possitively excellent, this whole thing. :D

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