Halstead and Ruzek were tailing Hailey to wherever she was heading. They used tailing in the lightest sense because she was a very trained Detective, who could well, detect a tail put on by her co-workers.

Halstead's phone lit up with Voight's number on it so he gave a quick nod to Ruzek to answer it, preferably on speaker, as he was still driving. "Yeah boss," Ruzek answered.

"Where does Upton keep her CI files," Voight asked.

Both men shared a glance. "On her computer, somewhere," Halstead answered. That was an odd question from Voight.

"Atwater went through her computer and found her CI files and nothing for a Kennedy Rose. Or anybody starting with K anyways," Voight explained.

"Maybe Upton didn't put her on the book," Halstead said.

Voight snickered. "Come on, Halstead. Upton is way too by the books to not put a CI down that she is actively working."

Ruzek was thinking. "Boss, how long was she in Robbery/Homicide?" He was starting to realize there was a lot about Hailey Upton that he didn't know. A lot. And she wasn't a willing partner to open up either.

"2 years or so," Voight answered.

"What if she put her on the books there and then never transferred the information. Maybe it's an old CI that she wasn't working and the debt was paid?" Ruzek hypothesized.

"That's actually a good thought," Voight said. "Where is Upton now?"

"At a coffee shop," Halstead answered. "Not sure who she is meeting but obviously somebody. It's too small for Ruzek or I to go in and see."

"Just keep on it. I'm going to go talk to some of those guys who got indictments handed down from Guns and Gangs and see what was going on when Upton was in the unit."

Hailey entered the café, scanning around for familiar and unfamiliar faces. She knew she was wanted now, so she also made note of every exit and a way to get to them. She spotted the face she was supposed to meet and slipped into a booth.

Kennedy Rose Boese was already working on a coffee when Hailey sat down. "Hailey, it's good to see you."

"Really Ken, now!? Of all times?," Hailey raised an eyebrow. "Everything was going great in my life for once. And now this."

Kennedy laughed. "May or may not have heard that you landed in Intelligence. How did a girl with a moral code like yours, end up working with Hank Voight?"

Hailey raised another eyebrow. "You, my dear, know too much."

Her former CI smiled. "You look good though. Happiest I have seen you in a long time. Any boyfriend? Husband?"

Hailey laughed and looked at her coffee. "Because I have time to date, right."

"There's someone, don't lie. I know that look, I've seen it before. A guy named Mike comes to mind."

"There's someone. It was a one night stand."

Kennedy whole heartedly laughed. "A one night stand that might turn into something more? Where have I heard that before?"

"Your relationship is probably the only one that actually worked that started from a one night stand in a dive bar. Oh and while high as fuck." Hailey had heard all about it the next day from Kennedy, a couple years ago and told Ken to forget it ever happened, it was a one night stand. Turned out, it wasn't just that. Kennedy married that one night stand a year later.

"You're probably wondering why I sent that text," Kennedy asked, nonchalantly, directing the topic to why Hailey was meeting her former CI.

Hailey took a sip from the hot coffee and just leaned against the back of the booth. She knew why Kennedy had texted her. Despite Ken paying off her CI debt, Ken owed Hailey a lot. A lot for why she was sitting in a coffee booth and not in jail. "I have some suspicions. When did he get out?"

"Yesterday. I just found out today. He showed up on my steps at 6 this morning and I told him to get lost, in some more colourful language. He looked like hell, but that's besides the point. I was so mad, I was seeing red. But the whole time I could think was that he was going to rain absolute hell upon you for what you did all those years ago to me and to him. Although, I'm not surprised they gave him early release."

Hailey sighed. "He gave someone up."

"It wasn't like he was squeaky clean and this was his first offense. He's worse than Hank Voight," Kennedy replied.

The Intelligence Detective scanned the coffee shop to make sure no other unfriendly faces had joined. She didn't relax any though. "I am aware."

Kennedy sighed. "Anyways, I wanted to give you and Rixton, in a round about way, a heads up. I know where you to play into it and how much he hates you but I'm not entirely sure where Rixton plays into this, other than I know he was the only one to not get indicted."

"I appreciate it. I really do. You sure about telling me this information?"

"Hailey, I owe you so much. You're the reason I'm still alive. I may have paid my debts to the Chicago Police Department as a confidential informant, but I like you more than just the Detective who got me out of a hot mess. Plus, I don't want to see that bastard succeed in getting revenge. Giving you a heads up was the best and only thing I could have done."

Hailey finished her coffee. "I have another stop to make, but I really appreciate it, Ken. Next time, don't be such a stranger. I want to see those twins next time, " she said as she got out of the booth. "And possibly John, just to get living proof that the two of you actually worked."

Kennedy laughed. "Oh I will bring him. I'll see ya around. Oh and… Mike is doing great," Kennedy smiled and laughed again as Hailey shook her head, leaving.