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doesn't make any sense, till it does

Summary:

“I know you’re busy and this is asking a lot,” Hailey sighed and opened her laptop. “But, if I send you some of the files, do you think you could work up a profile?”

“You know I love a good mystery…I’ll see what I can do.”

“Thanks Rollins.”

Notes:

I wasn't exactly planning on extending this little universe I've somehow created; but then this little idea came to me and I couldn't stop thinking about it. And then I realized that Hailey and Jay deserve more of their bubble of happiness that I fear the writer's won't give them - even when the shows finally come back from this never ending hiatus. So I'm going to give these versions of them as much happiness as I can.

I am also a sucker for any and all crossovers and for Hailey and Amanda interacting/being friends outside of work, so obviously that plays another role in this.

Chapter 1

Notes:

(See the end of the chapter for notes.)

Chapter Text

April 2026


The squad room had slowly emptied out, as detectives trickled out, as their Seregant told them to call it a night. But one very stubborn detective still sat at her desk, pouring over the case files as if something was magically going to fall into her lap. And well, stranger things have happened. 

“You sure you’re not going to head home?” Miller asked, stopping by her desk on his way out the door. 

“In a minute,” Hailey responded, not looking up from her laptop. She heard footsteps retreating, just to return a few minutes later and suddenly a granola bar was being tossed on her keyboard. Hailey turned towards him with a raised eyebrow. 

That's  all I’ve got on such short notice,” Miller told her with a shrug. “Don’t stay too late, Upton.” 

“Brewer said the same thing before she left.”

Callahan walked up to them, clapping a hand on Miller’s shoulder. “And we’re repeating it and it’s not just because of the obvious.” 

Hailey just rolled her eyes. While she appreciated her team looking out for her - she still wasn’t quite used to it and didn’t know how to handle it. 

“Tom,” she said, glancing at Miller. “Wesley -” she turned her gaze to the other detective. “I’m a big girl.” 

Miller chuckled. “We are well aware. Just like we are aware that you could kick our asses even now,” he waved his hand towards her. “But we wouldn’t be us if we didn’t at least try.” 

Hailey picked up her phone and opened the clock app. “Here, if I set an alarm, will that be good enough for the two of you?”

Callahan scratched his chin. “It’s a start ; but I think we all know you’re not really going to listen to it.”

The bickering went back and forth for a few more minutes, before Miller and Callahan finally took their leave. Hailey couldn’t help but laugh. The camaraderie that she’d found with the entire team at the special investigations unit was one that she’d never experienced before and she had to admit, it was nice. Sure, there was some back at Intelligence at least in the very beginning; but somewhere along the way, it'd gotten lost. But this was completely different. 

 

Hailey groaned, tossing the crime scene photos down on her desk, shoving away the pictures of their four missing teens along with it. They’d already been working this case for well over a week and were running out of leads and getting nowhere fast and she was getting more and more frustrated the longer the case dragged on. 

Though Hailey was stuck to her desk for the case and it was driving her insane that she couldn’t be boots on the ground. So she’d taken to doing the only thing she could do - look over the evidence, through the databases, trying to find something - and maybe she was overdoing it a little bit. But these cases were hitting her harder than normal. 

“Upton!” McAllister called, stepping out of her office. “What are you still doing here? After I’ve sent everyone home? Go home, get some rest.” 

“I just need something - anything, we need something to click already,” Hailey immediately said, glancing up at her Seregant. 

“It’s after seven,” McAllister walked across the bullpen until she was standing in front of Hailey’s desk and leaned against the edge of it. “And we’re not going to get anywhere if you wear yourself out…this extra stress isn’t good for you or the baby.” 

Hailey sighed, running her hands over her swollen stomach. It still shocked her that in just a few short months, there was going to be a little baby boy here in the world. “I just… I feel like I’m letting these kids down.” 

McAllister leaned forward, putting a hand on Hailey’s shoulder. “We can only do our best in this job, Hailey. And you’re on the best damn cops I’ve ever seen come through those doors. I don’t know how it was in intelligence; but you have nothing you need to prove here.”

“I was barely here for a year before I got pregnant and put on desk duty, Sarge,” Hailey said, her voice soft. “And I don’t want it to seem like I’m not holding my own.” 

“It was just over a year ... and well, your closure rate and history within the department, along with your quick rise to detective speaks for itself. Trust me Upton, I know what kind of cop you are and what you’ve done for SIU in the last two years.”

Hailey closed her eyes and let out a breath. It was still kind of a shock to her when she’d transferred to the Special Investigations Unit and met Casey McAllister - whom Hailey thought was a no nonsense hard ass Sergeant, and in a way she was; but she was also kind, thoughtful and cared about her team, always above the law and  looked out for them with no ulterior motives. 

McAllister almost reminded Hailey a little bit of Captain Benson. McAllister was the complete opposite of commanding officers that Hailey was used to and she was still working on becoming accustomed to her, and to SIU even two years in. 

Trying to shake almost seven years in Intelligence and even longer with worse cops was kind of hard. It would probably take more than just two years to do that. 

McAllister tilted her head towards the staircase leading to the lobby. “Go home to that husband of yours.”

Hailey smiled and ducked her head. “He’s probably also working late.” 

Or he’s standing right behind you.” 

Hailey’s head spun around to find Jay standing just a few feet away, a lopsided grin on his face. “What are you doing here?”

“Taking you home apparently,” he turned towards McAllister. “I’ve got it from here Sarge.”

“Your wife is very stubborn, Sergeant Halstead,” McAllister replied before walking back towards her office. “I expect you to be on your way out when I come back out here,” she called over her shoulder. 

“Come on Hails,” Jay said, stepping closer to her, placing his hand on her shoulder. “Let’s get you home.” 

“What about your case?” she quipped, raising an eyebrow.

Jay just shrugged and dropped his hand. “We hit a wall too and I sent the guys home - or well, I tried to; but Burgess and Ruzek were the only ones who actually took me up on it. Torres was just stubborn enough to stick around and I don’t think Atwater wanted to leave him there alone.” 

“Torres is almost going to become a mini you.” 

“Still trying to work on his work-life balance,” Jay admitted, letting out a breath. “Hell, still trying to work on mine running a unit I never thought I would.” 

Hailey knew Jay hadn’t exactly planned on taking over Intelligence when he took the Sergeant's exam - wasn’t even on his radar; but a few months after he passed the exam - a stray bullet had taken out Voight and the CPD brass hadn’t hesitated to offer the position to Jay, but he had.

“Why don’t you want to take it?” Hailey asked as they were curled up on the couch, her head against his chest, listening to the beat of his heart that she swore quickened when he told her about the intelligence offer. 

Jay ran a hand absentmindedly over her arm. “It was intelligence that almost broke us. And maybe a part of me is afraid of that happening again.” 

Hailey shifted on the couch until she was facing him. “It was Voight and his off the book ways and the domino effect of those choices that almost broke us.” 

“I just –” Jay started; but stopped as if he didn’t know exactly what to say. 

“You went away to Bolivia to find yourself,” Hailey reminded him, reaching over and grasping his hand in her own. “To get back to that man I fell in love with ... and you’ve come back to that man. And that man could easily turn Intelligence back into the team it was.” 

“I can’t lose you again.” 

“And you’re not going to, Jay… You’re not going to be under Voight’s shadow anymore.” 

Jay turned towards her, so many emotions warring in those green eyes as they stared at her. 

“Intelligence isn’t the only unit in Chicago, I’m not saying that you have to take it,” Hailey told him. “But it seems to be one of the only ones with an open Sergeant's position. You did always say running that particular unit was once your dream - maybe this is all a sign.” 

“Thought you didn’t believe in those?”

Hailey chuckled. “Maybe my damn husband is rubbing off on me.” 

“So I guess that means I too need to work on that work life balance,” she said, chuckled slightly. “Especially now.”

Jay leveled her with a look and Hailey relented, letting him help her to her feet. He helped her slip her arms through her jacket, pushed her chair in while she got her things ready. “Did McAllister call you?”

“Yeah. She’s just worried about you too,” Jay said, squeezing her shoulders. “Look Hails, I know you’re invested in this case and I’m not faulting you for that. I understand it; but you’ve still got to take care of yourself.” 

Hailey ran her hands over her swollen stomach. “And this little guy.” 

“And the little guy,” Jay echoed. 

Jay placed his hand over hers, a smile on his face and a look mixed with love and maybe a little disbelief in his eyes - as if he can’t believe they’re here. If Hailey was being completely honest, she felt the same way. Three years ago, when she took off her wedding ring and tried to put this life and Jay behind her (even if she failed) - she never would have dreamed they’d be here.

“You’re still here?” McAllister called, sticking her head out of her office and interrupting their bubble. 

Hailey let out a sigh. “I’m going, I’m going,” her eyes flickered towards her Sergeant. “But you’re still sticking around?”

“I’ve got a few more things to take care of here. But don’t you worry about me, Upton. I’m not the one growing a whole ass human.” 

Hailey laughed. “I’ve got it, Sarge. Trust me.” 

She reached for her laptop, sliding it into her bag along with the case file on her desk. Jay wrapped his arm around her shoulder, leading her away from her desk towards the hallway that would take them to the elevator and down to the lobby. 

“You just want to pick up some take out on the way home?”

Almost as if on cue, Hailey’s stomach growled and she knew she wouldn’t be able to wait for them to fix something. “Yeah,” she placed a hand on her belly. “Don’t worry, little guy. We’re gonna get you some food.” 

The only answer she got was a kick where her hand was. 

 

Jay had slipped away to the shower after dinner; but Hailey found herself still thinking about the missing kids, not being able to put it out of her mind. She had a feeling that between the case, and the boy currently playing drums against the bottom of her ribs - she would sleep tonight. 

Hailey pulled her laptop out of her bag where she’d left it in the armchair before settling herself down on the couch. She reached for her phone before thinking better of it and sent out a text. 

You’re not busy are you? <

A few minutes later, Hailey’s phone buzzed with a response. 

> Just finished fighting with a stubborn toddler over bath time.

Hailey couldn’t fight the laugh that bubbled out of her, imagining her own future in a few years if the little one currently growing in her belly got even the slightest bit of her stubbornness. 

It’s about a case. You got a minute? <

> Can’t say we won’t get interrupted by a seven or ten year old. 

> No one wants to sleep anymore. 

> But what’s up?

Hailey pressed the call button on her phone before chickening out and pressed it to her ear. 

“So it’s serious then?” the voice on the other end asked. 

Hailey tucked a stray strand of hair behind her ear. “Might be easier than trying to type it all out…. But you’re good at getting inside the heads of psychopaths, right?”

“You think you’ve got one?” Amanda asked and Hailey immediately heard the intrigue in the other woman’s voice. 

Hailey found herself giving some of the main details of their case, rattling off any important facts that came to her mind. “And I’m not sure if it's the pregnancy brain or what, but this damn thing is driving me insane.” 

“That’s a likely culprit.. Trust me, I’ve been there three times.” 

“I know you’re busy and this is asking a lot,” Hailey sighed and opened her laptop. “But, if I send you some of the files, do you think you could work up a profile?”

“You know I love a good mystery…I’ll see what I can do.” 

“Thanks Rollins.”

Notes:

I don't know how long exactly this is gonna be; but I'm hopeful it won't be too long and I thank you if you want to join me on this little journey.