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English
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Published:
2020-06-09
Updated:
2020-06-11
Words:
4,295
Chapters:
4/?
Comments:
17
Kudos:
105
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2,102

A Tale of Two Organizations

Summary:

Intelligence clashes with an FBI unit that comes to Chicago. Their casual camaraderie contrasts with the no-nonsense approach that the FBI takes, and Jay in particular clashes with the unit's Agent In Charge, Hailey Upton.

But there's something between, something that he can't quite put his finger on. It might take him months, or even years, but he figures it out.

Notes:

the first two chapters were originally posted on tumblr, but i liked this idea, so here we go! updates probably won't be EVERY DAY but we'll see how motivated I get ;) some edits were made to add detail.

Chapter Text

“Are you serious? Just like that?” Jay demanded, following Voight into his office. “We’ve been tracking this trafficking ring for weeks, and you’re going to let the Feds get their paws all over it?”

Voight let out a breath.

“They have jurisdiction over us.”

“That’s bullshit.”

“That’s how it works. I’m sorry, Halstead, I’m just as frustrated as you over this. But at least they’re working with us.”

Jay rolled his eyes. “Yeah, right.”


The first day with the Feds was a mess. Everyone kept talking over each other and none of the files were organized, so they got almost nothing done, which was infuriating to no end. He spent a long time trying to keep the agents from messing up their whiteboard, which they seemed to have a disdain for, which made him like them even less than he'd liked them the first time he met them. 

They were wasting time.

Jay made eye contact with one of the agents- a small blonde, who stood in the back, staring at the situation without saying anything. She held his gaze for a long, tense moment before clearing her throat.

“Here’s what we’re going to do. We’re going to split into groups. CPD in one and FBI in the other. We’re going to compile our evidence in a civilized manner and we’re going to present them to each other, like grown-ups,” she said, and the other agents fell silent. Jay raised his eyebrows- this agent seemed to have more control over the room than he'd anticipated. She just seemed like a random agent from the unit, but now he wasn't so sure. “Are you all capable of that?”

Jay snorted. “No offense, agent, but we’re not schoolchildren. This isn’t a group project. This is a drug trafficking ring we’re talking about.”

The blonde agent stepped forward, blue eyes blazing. “I don’t see any adults in this room, do you, detective? Someone has to play teacher or no one will learn anything.”

With that, she turned on her heel. “Agents, you’re with me.”

In that moment, Jay decided that he hated her. Whatever her name was. 


The next day, Jay came into the bullpen at the normal time, to find that the lights were already on and someone was working in there. 

That someone being a slight, petite blonde in a blazer.

Definitely not one of the members of Intelligence.

“How’d you get up here?” 

Agent Ponytail jumped, spinning around in her chair- his chair, rather. “Your desk sergeant buzzed me up," she said, tilting her head to the side, which made him feel almost as if he were the one out of bounds.

“What, the presentations yesterday not enough for you? Did we score too low for your standards?” 

Deep down, Jay knew he was being an ass, but he didn’t care. There was something about her that got under his skin.

“Those presentations only scratched the surface. I’m organizing my team’s evidence and looking for yours for things that we missed,” she answered, eyebrows raised. “We needed to get something done yesterday, and we did. But it’s not enough.”

“Then why did we waste our time?”

“It wasn’t a waste of time. We already had a few breakthroughs, if you remember- which comes from looking at evidence in a different way. Believe it or not, I know what I’m doing.”

Jay blinked. He didn’t know what to say to that. 

“Well, next time you come up here, be out of my desk by 7:15,” he said finally, before walking away.


On a raid the next day, an FBI agent blew his cover by forgetting to take off his wedding ring.

The case went downhill after that.

Jay heard the shots over the radio, but by the time he got there, the firefight was over, and three agents, one officer, and two offenders were dead.


After that, it was like someone lit a fire behind the blonde agent’s- Hailey Upton, he learned- eyes. 

There was no one else who stayed longer or arrived earlier than she did. She ran her unit with an iron tight fist after the first mistake, double checking and triple checking every file, every wire, every word that they ever said or saw. 

Despite his intense disdain for her and her unit, he felt bad- it couldn’t have been easy to have lost three agents under her command.  They walked around the district with tired eyes and wore all black a week- their own version of funeral rites, Jay guessed. So almost two weeks later, after catching her half-asleep at his desk at midnight, he brought her coffee that morning.

Just once.

She approached Jay the next day, tugging him into the locker room without warning, which almost made him spill his coffee. Lucky for her, he didn't, otherwise he suspected she would have needed a trip to the drycleaner. 

“I need you for an undercover op,” she said without preamble.

He agreed, even though he didn’t fancy listening to her directions all the time.


The first thing she said to Jay when they saw Holden, the second in command of the ring was we need to leave.

“I’m not about to let him go,” he hissed, yanking her forward. “We’re six bodies in, in case you haven’t noticed.”

“We’re walking into a trap.”

“You can’t possibly know that,” he said, before following Holden into the run down old house across the street.

She didn’t follow.


“Ah, well if it isn’t little Intelligence boy,” Holden sneered, brandishing his gun when Jay rounded the corner.

And instantly, he knew he’d made a mistake. 

He heard three pops.

The first sent him sprawling on his back, pain jolting through his body from the form of the bullet.

The next two ripped holes in Holden’s chest, one just above his heart, the next, dead center.

And then he saw her. She looked almost angelic, with her bright eyes and blonde hair as she fumbled with his jacket.

“Why’d you follow me?” he managed, as he tried to catch his breath.

She didn’t answer for a long time, just checked his vest methodically, with an almost impersonal detachment. When she found no blood, she sat back on her heels and let out a sigh. “I care about you,” she said finally. “And I hate how much I care about you. Backup is backup, whether I agree with you or not.”

“Next time, do me a favor and take someone with you. Because I’m not going to be in Chicago every time you run off by yourself.”