A/N: I wasn't going to delve too much into the history of Skate. I was going to keep it vague. But then I started a Lost rewatch with karivalentina and we were analyzing Sawyer and Kate so deeply that this chapter sort of just happened. I'm glad it did, and I hope you like this little flashback interlude, even though it is angsty. I hope you like it because it is angsty. As with the rest of the story, it is AU, but inspired greatly by the show's canon. So special thanks to Kari, she helped a lot with the last chapter and with this one!

James vs. Kate

The first time James caught Kate with a tiny little bag of white powder, Kate smiled and told him it was confectionary sugar. They were strangers at a mutual friend's party, he was off duty, and she was far too cute to arrest. He let it go, and they didn't see each other again for a week.

After meeting again, they started seeing each other more often, but they didn't call it anything more than what it was. Kate had her own crazy life, she only came to James when she wanted a good time or a bed to sleep in. At first, James had no reason to complain. Then he started to have feelings for her, and that's when it all went wrong.

Kate wasn't faithful. But then she'd never made James a promise. The problem was that James wasn't allowed to see other girls. Any time he got close, every time he thought Kate was done with him and he found a one night stand, Kate would sniff it out and insert herself back into his life. She'd show up, asking James if he wanted to give it another chance. When Kate wanted to be sweet, she was the sweetest. When things were good between them, life almost felt normal. That's how it always started out. Much to Miles' dismay, James fell for it every time.

The second time James caught Kate with a not-so-tiny bag of white powder, she swore to him that it wasn't a problem. He reminded her he was a cop, and every time he let her get away with it she was putting his entire career at risk. That's when Kate made her first promise to James. She promised he would never catch her with cocaine again. She didn't promise that she'd stop having it.

The third time James caught Kate with an even bigger bag of white powder, he realized why it was so easy for her to hide her 'addiction.' She wasn't using; she was selling. She was only using James and his apartment as a safe place to go when things weren't going so well.

"This is how I make my money." she said, defiant as ever. "I'm not hurting anyone. You're the one breaking up families by putting people in jail."

That was the truth of it, from Kate's point of view. She hated cops, and she was using James to stick it to the ones who took her step-father away from her, the first man in her life that didn't beat her and her mom up when she was too young to understand what was happening. The cops hadn't done anything to save her from her real daddy, but once Step-Dad was caught with some harmless drugs he was gone from their lives forever.

It didn't matter how sweet or undestanding James was, or how many times he let her get away with it. Whatever he did to make up for the men in her past would not be enough. She wasn't ready to let it all go.

It's not like she's doing it on purpose. James would tell himself, over and over again. She can't help what happened to her.

It doesn't mean she has to hurt you. Another voice inside of him would say, a voice that sounded strangely like his friend Miles. You're living proof that you can make something better out of your life.

"And who are you to tell me what to do?" Kate would ask him. "I'm not your wife. I'm not your daughter."

It escalated into a screaming match and they didn't see each other for a while after that. James wasn't ready to be a father, figurative or not, and he sure as hell didn't aid and abet criminals in exchange for sex. He still couldn't bring himself to turn her in, but he didn't have to date her either.

"Daddy issues!" Miles would shout when Kate wasn't around. "Abort, abort!"

And that was always a big part of it, wasn't it? James was the authority figure, the one who felt an obligation to let Kate slink back into the house every time she threatened to run away forever. Who else was going to protect her, if he didn't? What would his own life have been like if his uncle had given up on him? But if James the cop was going to let her get away with dealing drugs, then James the boyfriend would let Kate get away with anything. Take advantage while you can, that was Kate's motto and she'd be the first to admit it.

He played the part of Kate's lost father figure a little too well sometimes. Kate eventually came back, claiming that she was done with drugs for good. During the brief period when Kate was actually living with him full time (or at least supposed to be), and committed to him as a girlfriend (or at least she said so), James got curious one day and checked her phone. It sure beeped a lot for a girl that wasn't dealing drugs anymore.

"It's just my friends." she said, the desperation in her voice matching the desperate motions she was making to get the phone out of his hands. He swatted her hands away, not thinking about the consequences. The messages on her phone were not about drugs. They were all from other men, texting her, calling her, saying things only James was supposed to say, in bed, behind closed doors.

"Give me the phone." she said, her voice hard and defensive. It didn't matter what was on it, James didn't own her. She grabbed for the phone again, and James clamped his free hand around her upper arm. He yanked her closer to him, hard enough to make her cry out. For a moment she panicked, the child in her recognizing the fury in his eyes. The look that soon took over her features was filled with so much pent up anger he almost forgot about what he'd seen on the phone. He didn't even see the first punch coming. She wrenched herself free and started hitting him and hitting him and he couldn't hit back. He guarded his face, taking Wayne's punishment for him so many years later, and Kate screamed at him with all the fury she had inside of her. She screamed for herself, and for her dead mother who'd never hit back, the mother whose only attempt at protecting her daughter was getting beaten up herself.

When she was finally through, sobbing too hard to have any power left in her punches, Kate left and slammed the door behind her. She left James sitting on the floor of his apartment, looking at his own shaking hands. His entire body was vibrating, like a tuning fork struck. He could finally hear the meaning of his place in Kate's life. He could hear Miles telling him not to be so rough with the suspect, and he could hear his own voice telling Miles he didn't have a problem, he wasn't angry, he wasn't taking out any frustrations.

James looked down at his shaking hands and thought maybe Kate was right. Maybe he was the bad guy. That's what the suspect said, just a teenager, sneering with bloody teeth at the police officer that had savagely punched him in the mouth just for calling them pigs. "An angry cop is the bad guy."

That was their lowest point. They both had things to be sorry for. Their frequent bickering and occassional blow out fights were no match for what had happened that day, and Kate stayed away for a long time.

Months later she showed up at his door with a black eye and a cheap brace on her left wrist. Her lip was trembling and she didn't get past the first two words before she was crying.

"I'm sorry." she said, tears streaming down her cheeks. She didn't say what for. Maybe she was sorry for hurting him. Maybe she was sorry she was ever born at all. It just broke his heart to see her crying like that, so lost and obviously alone. It always hurt more to be alone.

It lasted for a while that time, for too long, the cycle of keeping secrets and sorry, lies and sorry, cheating and sorry. James was not innocent. He slept with other girls. Those were the rules of the game - hurt me, I hurt you. Didn't matter who started it. Only that the cycle continued.

Kate never told him who gave her the black eye. His best guess was that, after kicking the shit out of him and leaving his apartment that day, she'd gone back to what was most familiar. He foolishly assumed that she'd stopped again once she came back into his life. It was easier not to ask questions when he was afraid of what the answers would be.

The last time James caught Kate with an entire brick of coke in her bag, it wasn't even about her breaking the law anymore. She'd lied to him so many times, used him so many times, expected him to do nothing about her bad habits so many times. It was the perfect excuse to let her go, the perfect symbol of what would always be between them.

"Get out." said James, without even a discussion on the matter. The brick was still in his hands and his vision was turning red.

"James, you don't understand." she said. It wasn't anger driving her words this time, but fear. He could see it, but there were too many lies between them. No trust. She was probably faking it this time. Wasn't she?

"If I ever see you again," James said slowly, anger seething between every word. "I'll arrest you."

Her protests were desperate. James was going to flush the coke down the toilet and send her away. She insisted that she really needed his help this time. You might as well just kill me now, she said. Don't do this, she pleaded.

Don't be the guy that finally gives up on me, is what she meant.

When Miles came home that night, and James told him what happened, the entire apartment was filled with doubt. Miles didn't quite believe James was through with her, and James wasn't sure he'd done the right thing.

Miles gestured toward the brick that sat right on their coffee table, in the middle of their living room. "If I'd found that thing?" he said, dead serious. "I would have arrested her."

"I know." said James, gruff and even more serious than Miles. A big part of him wished that had happened. Part of him thought maybe that would have been the safest thing for her, to teach her the actual lesson. He was staring at the drugs, a symbol of the demon in his life, and he wondered if protecting Kate from the law had only been to protect himself from Kate. He couldn't help feeling like he'd betrayed her, no matter how wrong she was. He just couldn't take it anymore. She never belonged to him. And he no longer belonged to her.

For a year he didn't know if she was alive or dead. She wasn't in Los Angeles anymore, that much he knew. Then he started to hear stories about her from their mutual friends, friends he saw less and less of as the years went on. He was sure they passed stories about him on to Kate as well. She's a survivor, he reminded himself. Not his burden to carry anymore.

The demon was gone, but ghosts of the past still haunted him. James accepted an invitation to undergo counseling for his anger problems at work. Truly repentant, the sessions helped him a lot. The fate of his parents was not his fault, and the fate of his ex-girlfriend was not his responsibility.

Things kept looking up for James. He received commendations and promotions. He learned what it was like to have a light heart. Then, one day, James realized he was happy. There was no drama in his personal life, and his work was going well. All that was missing was someone to share it with. He'd had his eye on that cute blonde from the morgue for a while, but she seemed out of his league. He was more of a one night stand type of guy anyway. The less he saw of each woman the better - for their sakes, if not for James. All he had to do was remember a fraction of the grief Kate had given him, and he thought it was better to keep a distance.

Good thing he'd been in an optimistic mood the day he heard Juliet was quitting.