Crowley didn't just become King of the Crossroads because he bred and trained most of the hounds of Hell. He mastered the art of the deal, perfected the double cross, he'd been to every crossroads on the Earth and even some that weren't on the map, at least he'd thought he had until he had been to Preya. He'd sold sin to saints for centuries. He knew how to read a soul, he could show up to a crossroads, look at some sorry sap and read them like a book instantly. Every little mannerism, every nervous tic, the way they avoided their gaze, the way they positioned their feet, the clench of their jaw, the clenched fists, and more than that, the way their soul glowed in their chest, just the right combination of bright and dark.
Angels were different. Archangels were completely different. Michael was a blank canvas. But Crowley didn't need to read him to know that he had lit a powder keg by patting him on the arm. He was taking a chance and he knew it by doing that, the fact that Michael was operating as an officer of the law in Preya, they were in neutral territory.
Maybe Crowley had a suicidal streak. He had one back then when he'd driven the dagger in, such was the Winchester influence. But he realised that maybe he was feeling sentimental, but it wasn't entirely towards the Winchesters. Perhaps he'd had a few too many drinks.
Crowley heard Michael speaking though he didn't look at him straight away. He agreed with every word, brows lifting in acknowledgement, because if he could go back to that moment, if he could go back to any of those moments he would change all of them, he would just make it so that he never met any of those damned Winchesters-- the world would have ended, sure, but maybe it'd be worth it. Maybe.
"Castiel might be the prettiest angel in the garrison, but he's not that bright," Crowley remarked dryly, "then again, we all have our crosses to bear. Perhaps this is our penance."