Sam couldn't resist the urge to reach out and pet Dean's hair. He still couldn't shake the uneasiness of the situation though. Henry had died to protect the key, it had to be something pretty big. He just couldn't shake the feeling that digging at the whole Men of Letters thing would be like poking a great big grizzly bear with a pointy stick.
"We don't even know how deep this thing runs, Dean, how big it is. We hadn't even heard of these Men of Letters before now. I just think we should be careful, y'know? I mean if that super-powered demon bitch from Hell followed Henry, who knows what kind of crap we're going to uncover?"