Maybe Sam wasn't the best influence. Not only was he letting a minor drink, but he was allowing one with bad history in relation to alcohol do so as well. Yet with all that had happened, what else could he do? Pat Jack on the back and tell him that everything was gonna be okay? No, that wouldn't work at all. He was the standing mascot for seeing how often that attempt at making things right had failed (both on himself and other people), so it seemed that other measures needed to be taken. They certainly weren't the best of the best, but so long as Jack stuck to his promise and turn this into a terrible habit, they'd walk out of this okay. Very hungover, but okay. Sam would just have to take it upon himself to keep an eye on him in the meantime. Until he was sure that he hadn't triggered something awful.
Sam did feel guilty about it. Terribly guilty. He was a recovering addict, he knew how hard it was coming back from something like that. But Jack had been hinting at it for a while now and the timing seemed appropriate enough. It was a day to crash. They had to get away. Tomorrow, they would get back up again. Even if that meant that they had to help each other in order to do so.
"If I wanted to swim in money, I'd go rob a bank or something." Sam set his empty bottle down and looked over at Jack, shrugging. "Or I'd send you to go get it for me. You could." Sam had been in the whole bank robbery situation before. He was really going after a shapeshifter at the time with Dean, but the cops didn't know that. All they saw was two wanted men and a vault full of hostages. That was all they needed to see.
Picking up a new bottle, Sam leaned forward against the bar and looked at Jack curiously, not quite sure on what he was getting at. "How'd I do what?"