Neither Winchester is all that stable by himself, frankly. I think Sam would last longer, but he's going to be as dangerous and unpredictable as Dean would be by himself, in different ways.

I'd vote for more dangerous and unpredicatable, myself. Dean would turn some of his sadness and anger inward, but I don't think sam would.

Dean spent a lot of time in his father's company and Sam's company. All of his other 'friends' were in the business and sporadic contacts at best. Sam actually spent time in the world outside of demon hunting- made normal friends and more regular human connections with plans for the future. Each time the important people in his life have been ripped away, by things he can't explain to most people; Sam has taken a deeper dive into the black pool.

and taking dean away for about 6 months, ( 100 Tuesdays plus 3 months from Wednesday) , push Sam even if Dean lives.

The Trickster was stupid in the typical Trickster way. He had no understanding of human emotion/motivation.

The Trickster was stupid in the typical Trickster way. He had no understanding of human emotion/motivation.

You think? I think pushing Sam to stare into the abyss was exactly his intent.

yes, but he said " all the sacrificing you brothers do for each other leads to pain" - that isn't going to change - it is what they do.

It may not be so much inhuman perspective as selfish hedonism that prevents the Trickster from understanding them fully. For whom would he sacrifice his happiness?

that works too - it just seems to be what confounds the Trickster in stories

My theory is that Ruby put the Trickster up to this. His argument to Sam about the futility of self-sacrifice seemed designed to get Sam to "prepare for this war" the way Ruby wants him to do. And in their last encounter, the Trickster really liked Dean, while he didn't think much of Sam one way or another; so his focus on causing Sam pain seems rather unmotivated, really.

I like that! I've been wondering why the trickster cared so much about teaching Sam that lesson. I can see it if Sam was being cocky/full of himself about saving Dean, because then it would be his just desserts, but he really hasn't been.

the cut of him making the bed and eating especially made my skin crawl.

I only saw Taxi Driver once and I don't remember it in detail. I understand that Travis Bickle is the De Niro character [link] and I'm guessing that line was to reinforce the creepy cold blooded scenes that we watched of Sam, but can someone explain the "in a skirt" part to me? I'm feeling really dense, but I don't get it.

I'm glad you asked Austin, because that's not part of my cultural knowledge either.