He's long defaulted to following the letter of the law since he couldn't follow the spirit of it. Even now, his measure is changing - but Lucifer wasn't the only angel who measured another's worth in their loyalty to their brothers.

"Sam Winchester is more trouble than he is worth." Both were, which didn't mean Raphael wasn't willing to revisit some of that trouble back onto them. He's really rather enjoy doing just that.

"No, they didn't." He wasn't going to let it rest where it was.