Family Matters/All Dogs Go To Heaven/Clap Your Hands if You Believe
 
Once Dean got the bombshell from Castiel that Sam was soulless, his attitude changed.  It was no longer a game of trying to guess what Sam was.  His focus switched to doing whatever it took to get Sam's soul, thus the real Sam, back.  In the meantime, he set the rule that he was calling the shots.  He wasn't going to give Sam equal footing given his state.  That worked out okay in "Family Matters" when Sam chose to stick with Dean, and also in "All Dogs Go To Heaven," but by "Clap Your Hands if You Believe" Sam started having doubts about getting his soul back.  Dean suspected as much too when Sam said no to the leprechaun's offer (that still sounds pretty absurd, doesn't it?).    

Still, in all those episodes, this is the Dean that stands out most in my mind:  



Okay, maybe this too:



Caged Heat
 
Dean's issues fell with another family member, Samuel.  Oh man, I definitely don't want to be on the wrong side of this:

 

He just doesn't take backstabbing well, does he?  At least Sam was sticking by him, until the end.  Castiel's warning to Dean is pretty clear about what could happen if he gets Sam's soul back.  Surviving could be worse than dying.  "Paralysis, insanity, psychic pain so profound that he's locked inside himself for the rest of his life."  Dean decides the risk is worth it, they can deal with the complications when they get it back.  Dean's able to make that choice, but an eavesdropping Sam doesn't appreciate that decision.  
 
So why is Dean so easily able to make that choice?  It's clear he's not seeing soulless Sam as an equal.  He's seeing him as someone he has to make choices for.  Even Crowley and Meg say that getting back his soul is a bad idea.  At the end, when Sam raises the issue, Dean won't back down.  Sam says he's telling Dean something he doesn't like.  This actually parallel's Sam and Dean's struggle through the entire series.  All Dean has ever wanted is Sam to be human.  To act human, to stay human despite the demon blood inside of him.  Here is no different.  No soul is not human.  He's willing to risk Sam suffering in very human ways in order to keep that humanity.  The un-human Sam begs to differ, for his only purpose is survival.  
 
Appointment in Samarra
 
It's the ultimate, mega huge, slap you in the face Dean Winchester character test.  Dean  is desperate now.  He has himself killed (for a few minutes anyway) just so he can talk to Death and ask for Sam's soul back.  He even wants Sam's soul returned undamaged so that he can convince Sam to go along with the plan.  It's obvious he needs his brother back in the worst way when he gives his letter of final words to Dr. Robert.  It's addressed to Ben, not Sam.  He knows that whatever he says, Sam won't care. If there's one thing consistent with Dean's life though, these risky choices come with a high price.  

Dean gets to be death for a day.  Why?  If you were Death and you had a chance to teach the one guy who wrecks the natural order on a regular basis a lesson, would you pass that up?  This lesson has been a long time coming and as hard as it is to see Dean go through that, he had to see the consequences of his choices.  His stubborn defiance kicked off a chain of random events that ended up getting innocents killed.  Not to mention the person he chose to live, a 12 year old girl, would have chaos and sadness follow her the rest of her life now that she's alive.  Wow, that sounds very familiar.  Sam Winchester anyone?   Or lets take it farther.  Mary made the original deal and see what's happened to their family since then?  That's another topic though.  
 
Dean must see this first hand, for he's always been a "seeing is believing" kind of guy.  He gets the message.  Knowing what he knows now, he would have killed the girl first.   He has new appreciation for the natural order, but that only puts him in more of a pickle with Sam.  
 
Dean decides when he makes the deal with Death that a wall in Sam's mind is better than nothing.  It's a compromise he's willing to live with.  He knows why he must take this awful risk.  Because as he's learned, anything not human is usually dangerous.  RoboSam will stop at nothing, and his attempt on Bobby confirmed Dean's worse fears about Sam remaining soulless. 
 
Ever since season two, Dean has done everything he possibly could to avoid making the most horrific choice he could, killing Sam if he became too much of a threat to humanity.  It's been his unwavering commitment to save Sam from this awful fate.  He's always known that if he couldn't save Sam, he'd have to kill him.  After he stopped Sam just in time from killing Bobby and they had him restrained in the panic room, Dean sadly knew there was only one choice left.  He couldn't leave Sam locked up and he couldn't let him go.  He never said it, but his hopeless expression as he went upstairs for a breather said it all.  He'd have to kill Sam.  This is indeed Dean's worst nightmare come true.  Lucky for him, Death was upstairs waiting.  
 
Even at the end, when Sam was screaming, Dean knew this was his only option.  It still hurt him to do it though.  Sam's scream reminded him of the fact that no matter what, he was still putting his brother through a lot of pain and risk.  He wasn't about to defy the natural order again though.   



Like A Virgin
 
Dean at this point desperately needs some relief.  It's been ten days since Sam's soul was put back in and he remains in a coma.  Dean's now frantic with worry over if Sam will wake up.  Summoning Castiel doesn't help.  "If you wanted to kill your brother, you should have done it outright."  Dean's look of guilt after Castiel left angry says it all.  He had no choice, Sam couldn't walk free (I loved his T1000 opening fire line).  Still, what was Sam up for when/if he wakes up?  
 
When Sam awakes with no memories of Hell or being soulless, Dean is more than willing to accept that as good (plus a meaningful good old fashioned brotherly hug doesn't hurt).   "As far as I'm concerned, it's a gift horse. And I'm not looking for teeth. I'm sending Death a damned fruit basket."  However, he's got a new problem.  Sam knows something isn't right.  The wall is itchy and he wants to scratch.  
 

 
Dean won't talk about what happened in his life in that year and a half either, especially with Lisa and Ben.  Part of that is too much pain, but another is he doesn't want Sam remembering why they ultimately split up, because Sam returned.  That would be kicking that wall.  It's really sad for Dean, having his brother back, but not being able to talk to about that hole in his life.  In the meantime though, Dean is looser and feeling better that "the real" Sam is back (that point I'll debate in A Deeper Look At S6 Sam Winchester).  He's starting to have fun again.  That is until Mother of All emerges.  Now he's got a new problem.  
 
Mannequin 3:  The Reckoning
 
Dean gets to say "I told you so."  Sam scratches the wall and the consequences are dire.  Actually, it scares the crap out of Dean more than Sam.  He decided to give Sam latitude and try it his way but when things got dicey, he pulls authority.  No more digging into that missing year.  Overprotective big brother is something too hard to shake.    
 
Dean's forced though to deal with his "year."  Ben sends an emergency call and Dean is practically shoved into the Impala by Sam to go check it out.  It forces Dean to have an honest face to face with Lisa.  He had to see that Lisa was getting on without him, but convincing Ben is harder.  He has to leave, to say goodbye for their sakes, no matter how much it hurts.  It's clear he still doesn't want to let go though.  He also sees how hard it's been on them and knows he can't go back.  This really depresses him and his only comfort is a pep talk and a thank you from Sam.  At least he has his brother.  

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