Dick Roman's second in command did it to Dean, in Bobby's yard. And Dean also was in the hospital way back in Season 1, when he got electrocuted. (1x12 Faith). Plus, they both were in the hospital in the Season 2 opener, with Dean hanging between life and death (2x01 In My Time Of Dying)
Yes, poor Sammy, he's completely exhausted. Lack of sleep, and Hallucifer wearing him down, no wonder he feels that way. It was hard for Dean to understand, while at the same time he's desperate for Sam not to give up.
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