Regret

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Feels?

There are a few things that all of the Winchesters have in common.

The incapability to remain dead.

The borderline obsession with flannel.

The incredible ability to lie and smooth talk their way out of just about everything.

The utter denial when it comes to any of their feelings, because it's more difficult to lie if you feel everything.

The love of old black Chevys.

The desire to eat Winchester surprise, even if it's always a disaster.

But there's another thing the Winchesters all have in common, even if they don't realize it.

Regrets.

Mary Winchester blames herself for her sons' entire lives. She believes that it's all her fault that they are in the hunting life, and at the end of the day, it kinda is. She blames herself for every bad thing that happened to Sam and Dean, and every bad thing that will continue to happen. She regrets her deal with Azazel more than anything, and if she could go back in time and fix it, she would, no matter the cost. It's her fault that she burned on the ceiling, that Sam was cursed, that Dean was neglected and abused and had to grow up too fast, that John.... Well, that John became the man Sam and Dean knew, not the one she loved. She continues to blame herself the more she learns about her son's lives. It's her fault Sam never got the life he wanted. A lawyer, not a hunter. Her fault that John had to learn the hunting life and struggle to avenge her and keep their boys alive at the same time. All her fault. 

John Winchester blames himself for his son's entire lives. He believes it's all his fault that they grew up the way they did. Too fast, no friends, barely an education. He still has no idea how Sam managed to get into Stanford in the first place. He blames himself for every bad thing that has happened to them, because it only happened because he was selfish. He should've dropped them off at an orphanage the second he dove into the hunting life, instead of toting them around and letting them raise themselves. But Sam and Dean were all he had left of Mary, and he couldn't bring himself to let them go, no matter how much it hurt them. If he could go back and time, he'd change it. He'd offer to get Sam that night, so that he burned instead of Mary. And if that didn't change anything, then he would leave the boys with someone, instead of taking him with him. Dean would've resented him for life, but it would've been better than the life his son had. It's his fault that Sam and Dean are the way they are. His fault that Dean won't talk about anything- because every time he had tried as a child, John had shot him down, unable to deal with his son's emotions when he couldn't even confront his own. It's his fault. All his fault.

Dean Winchester blames himself for everything. He believes it's all his fault that Sam's still in the hunting life. He should've left Sam at school. He was happy there, and Dean never should've dragged him back in. He should've done a lot of things differently. He blames himself for John and Mary's death too. John sacrificed himself for Dean, and Dean still hates living with that. It should've been the other way around. Sam has unknowingly convinced him that he's wrong in that idea. Sam would always rather have Dean than their father, but Dean still despises the fact that their dad died for him. He blames himself for Mary too. The longer he thinks about it, the more he realizes that when Cas sent him back to fix things, he led Azazel right to his mother without realizing it. It's all his fault Mary made a deal and burned. All his fault that they were all in the hunting life. If he could go back in time, Dean would've left it alone. Sat on a street corner and waited until Cas took him back, not touching anything. The only downside to that Dean saw was that they'd probably be driving a stupid hippie van instead of a Chevy. Dean blames himself for every bad thing that has happened to his family. It's his fault. All his fault.

Sam Winchester blames himself for everything. He believes it's all his fault, that he's still the baby Azazel cursed.  Everyone he gets close to dies, and everyone who doesn't die suffers. Demon blood wasn't the curse- it's just him. His existence in itself is a curse. The angels knew that, and so does Sam. Dean's probably the only one who's never thought it, even when John told him. Sam blames himself for Jess's death, and for the deaths of everyone he failed to save. It's his fault that Lucifer rose. His fault that the Darkness was released. And out of it all, Sam just regrets how much he let everyone down, especially his brother. If he could go back in time, Sam would probably end it before it could all begin. Take himself out of the equation, just to stop the suffering. It would kill Dean and John, he knew, but in the long run it would be worth it. He's the reason why Dean can never escape the hunting life. They just keep dragging each other back in. Sam tries to get out, but Dean never even got the chance to escape. The one time he did, Sam pulled him back, and he never tried again. It's his fault. He's the cursed one that started it all. All his fault.

None of the Winchesters realize that they're all blaming themselves for the same thing, when really they had no control over any of it.

Cas knows this. He saw be commanded. He watched it all unfold. The choices the Winchesters wish they could go and back and change can never be changed because they were foretold to happen. Mary and John Winchester had to meet. Had to fall in love. Had to have two sons.

Mary Winchester had to burn.

Even Azazel didn't know how deep the plan ran. He didn't even know he was following it. So while Mary, John, Sam, and Dean may all individually blame themselves for the night a demon killed and cursed, it is not their fault.

No human is to blame for the night Mary Winchester died.

Nor, Cas believes, is any demon. It was out of all of their hands.

Cas blames Chuck. He believes that it's all his fault that the Winchesters are the broken people they are. And he's furious about it. Utterly furious. And part of him thinks that the reason Chuck keeps failing to return is because he doesn't have the guts to look Cas in the eye and admit to all the wrong he has done. Or to listen to all the things Cas has to say to him. 

Cas knows the Winchesters are not to blame.

But no matter how often he may try to convince them, it's no use. It's something all Winchesters have in common.

They all regret something they didn't even do. 

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