Halstead Imagines

Contract Killer

Very, very loosely based off of season 2 ep 3 of PD titled "The Weigh Station".

What if Hailey's story meeting Jay is a little different? And it's all because of one big bad decision and seeing Y/N.

Hailey looked through her binoculars at the man who, if she could help it, would be dead within 48 hours. She could make it 24 if she really wanted to, but she needed to make sure she was alone and that she had time to get it to whoever needed to see him dead. Even though she was the one tasked with killing him, she had no idea who actually put the bounty out on his head. Someone she had put in prison (ironically, the reason they were in prison was for being a contract killer) when she worked in robbery-homicide had called her once they were out and told her about this opportunity. And, since Hailey had been fired from her job for a rumor that went around that she was sleeping with a superior officer and didn't actually pass the detective's exam (both were lies), she needed money, so she agreed to the hit.

A girl walked out of the house, surprising her. She looked too young to be one of Halstead's flings. She looked between 15 and 20 from where she was looking. Maybe she just had a babyface, though. Yeah, definitely just a babyface.

The girl walked outside and to her car with a backpack. She was starting her car when Jay Halstead ran out of the house and handed her what Hailey assumed was a textbook.

Shit, she thought, this girl's in high school or college, so it definitely wasn't a fling or a one night stand. If this was a younger sibling or relative that he was taking care of, then there was no way she was going through with this. When people were helping out their younger family members, well, that's where Hailey drew the line. She knew that Jay had an older brother, Will, but he was a doctor and could take care of himself. If Halstead had a younger sister that was still dependent on him financially or otherwise, well then there was no way she could do this.

Hailey pulled out her burner phone and called the burner number that was given to her in case she needed more information or she encountered any problems.

"JP," she started, "does Halstead have any siblings besides Will? There's a girl at his house and she looks too young to be sleeping with him."

She heard keys clacking on the other end. It took longer than she had expected. "Shit," JP said. "He's got a younger sister, Y/N Halstead. She's twenty and according to this, she lives with him since their parents are dead and she's in college. Need me to hand this off to someone else?"

"Yeah, you know I only did this for the money and my one drawback is people who are dependent on the people you want me to kill."

"What do you know about this guy?" JP asked. He assumed she didn't know much about him.

"They just told me that he was an ex-army ranger who killed innocent civilians in Afghanistan."

"God, they lied to you so hard, Upton," JP told her. "He's a detective with the Intelligence Unit of the CPD. And, he saved people overseas, he didn't kill them."

"Shit. I'm out. I'm definitely out."

Then, she hung up. But, she promised herself that he'd try her best to protect him. After all, she had taken this job, so maybe she could fix it by trying to protect him. She wasn't doing it for him, though. She was only doing it for his little sister. If it were just him, he'd be dead in less than two days.

***

You poured syrup on your waffles at the small diner you and your brothers had gone out to. It was a rare night where you didn't have any major studying to do, Will wasn't working or on call, and Jay wasn't working on a case or undercover, so you were all out for dinner together.