If he were to be more forthright with his replies, he would've said 'when I was done being dead' or something along those lines. That would place his alliance with Talon after Ana's attempted assassination (Though were they really aiming for Ana? Or was she simply in the wrong place at the wrong time?) But that would just put Jack at ease. Can't have that, now can we?

He hates that this conversation is happening, and he let it happen. Hell, he wanted to see how it would pan out, even if he'd replayed what possible outcomes it would've had in the past. Back when the wounds were fresher— angrier. He knew it wouldn't be good, but after a long while, revisiting the idea suddenly seemed like a novel thing. Guess he wasn't too far off the mark, since there's very little killing going on right now.

"Maybe..."

It feels like eons ago, when he used to have that sliver of idealism, lining the harshness of reality in specks of silver. Maybe what they were building was a good thing, the intentions were there, but it turns out Overwatch was just another cog in the machine. Used until it wore out, and forcibly removed from the picture. Of course, he'd admit that he had a helping hand in that, even if destroying Overwatch wasn't his intention.

To him, it was a tool. Being Blackwatch was probably one of the best things to happen to him, employing his own tactics of how he thought the world should be protected. Being given the power to do that, even without the title of Strike Commander, was more or less a blessing. At first, he'd thought being passed over for Strike Commander was a huge missed opportunity, but as time passed? It didn't seem too practical.

"...Maybe not. Did you think we fought because I just didn't give a shit?"

His tone suddenly grows snide at the end.