If nothing else, Jay is thorough. He knew every little detail about his current boss Arthur. PD suspected him of assault and half a dozen other vandalism or protection money charges, but no one had dared to flip on him yet.
In recent months all roads had led PD to Arthur, and his stake in a Bucktown bar called Molly's. The most recent is the complete destruction of the neighboring bar, Game Day. Jay is absolutely clear Arthur is dangerous, and still, he was in now. He got the job, and funnily enough, his first assignment was keeping an eye on Molly's.
He immediately did his research on the public faces. The owners all are firefighters or paramedics from firehouse 51. And he hated to think they knew what Arthur was up to. So, his first step was trying to befriend them.
It served both his jobs. He could report back to Arthur, but he could also suss out how much if at all, these people were involved. Or if they perhaps were victims too.
That much was the plan, at least until he stepped foot into Molly's and met Gabby. Gabriella Dawson.
A temptation for his professionalism and his heart.
He told himself the flirting is just to protect his cover and get close to her in the most professional way possible.
To gather information.
But his resolve was dwindling.
Fast.
Not even knowing her brother is a cop can keep his heart from getting involved, and he had been afraid of the day this all came to a head.
Jay's heart breaks the second Gabby's eyes register he is with Arthur, and her reaction is understandable, but he can't help himself. He has to try and talk to her. When all his calls and messages go unanswered, he gives up. For now.
Maybe in the future, when she is safe, he can go back and explain. Maybe Antonio Dawson can help?
He is still stuck in his head, in his undercover apartment, when sharp knocks pull his focus. Outside the door is the last person he expected, but the only one he wanted to see. Gabby.
Uttering the words, he hopes no one around hears. "You're a cop?" For a split second, he thanks his lucky stars, and what follows is as amazing and exhilarating as it is dangerous and maybe even stupid.
Being together. Having her close.
She almost turns into his lifeline, and it hurts he can't help her immediately. Gathering evidence against Arthur proves even more complicated than initially thought.
He can absolutely understand Gabby's anger at becoming a suspect after the Game Day fire. They all know it was Arthur. But knowledge isn't proof.
Staying rational and focused is becoming more and more challenging. Jay's drive to do this by the books and also keep his girlfriend safe are on opposing trajectories. A dangerous combination. Especially with his ambition.
His last ditch play is getting Gabby to provoke Arthur and being there to witness it all. He prepares carefully. Wears the wire, and when he is sure everything is hidden, he meets the man he just wants to arrest.
The last few months with Arthur had been hell. And he knows he wants out of this and have a spot in another unit. Antonio's.
But first, this case has to end. Hopefully tonight.
His heart almost stops with Gabby refusing to pay Arthur. It is a provocation, alright, and playing a very dangerous game. Especially after the man already smashed every piece of furniture in the bar once.
But the threat Arthur opts for is even more sinister. And also oddly perfect. He threatens to burn Molly's down just like he did Game Day.
Gotcha.
Jay allows himself half a second to rejoice before the situation escalates. The bar top is in flames, and guns are being drawn.
He acts on autopilot, steps in, and tries to keep the civilians safe. Civilians. They are all firefighters.
With Arthur arrested and handed off to uniforms, Jay finally lets himself getting taken care of.
In the skirmish, he'd caught a bullet, and he revels now in Gabby's fingers tracing across his chest. His mind supplies the images of past moments when they were as carefree as their situation allowed. But in his apartment, they were almost always in their little bubble.
Just them.
He observes her, and just the way Gabby bites her lower lip, he can tell something bad is coming. Jay always could read people, and with her, after getting to know Gabriella Dawson in the purest sense, it was even easier.
"I can't be with someone who has to be someone else for so long. I am sorry."
Jay can't say he faults her. Being undercover and having a relationship is not exactly a common or easy combination. And still, it hurts.
He played with fire and got burned.
Thanks for reading. I am absolutely sure there are some canon issues, but after the goodbye Jay and Hailey shared, my head went back to the start, so to speak, and well ... this happened.
I hope you enjoyed this little peek into Jay's mind when we first met him.
