Claire. His daughter, his one and only pride and joy taken away from him in a heart beat. This is why he let go. He let go for her. Claire and Sam had already fallen asleep on the couch when he walked in their house. He was now in heaven. He looked around for his wife, and of course there she was baking a pie in the kitchen. The best thing about this was that it wasn't a memory. It was them actually them.
The clock was ticking away. It was empty and cold. What had happened that night shouldn't have happened. The nurse came out of the room with an old caring face she's had to give this news to many times. He stood up and walked over to her.
"Their wounds were to severe, there's no way they would have made it." He dropped to his knees. The only people has ever cared about taken from him in seconds. Dean was driving back to the motel with Sam sitting next to him. His daughter in the car seat and tess next to her. The car that had ran into them was going way to fast. A drunk driver on the night of Christmas eve. What was he to do now but to go back to the motel and lie there. He finally had a normal life, like Sammy has always wanted. But Sammy no longer there. No one was. He was alone officially for the first time in his life and he couldn't take it.
He pulled the trigger. Dean Winchester, the one who always had a reason to never give up even when the battles were lost, pulled the trigger. But this wasn't giving up. This was letting go. This was going to bed on Earth and waking up in Heaven. Dean Winchester used to think that his Heaven would be joining Pamela at that rock show, or being with his mother, or even just keeping radar on Sammy. But Dean Winchester has grown up since then. He's had losses that changed his life dramatically, but had also met a few new people to bring him joy. Those people were his beautiful wife Tess and their gorgeous daughter. They left him a little early than Dean Winchester had hoped, but they stayed with him longer than he had expected.
He always thought that Tess was way too far out of his league when she glided into the bar on those graceful, rockety hips, but that never stopped Dean Winchester from blurting a cheesy line and sending a charming grin and a beer her way. He never expected her to stay, he always thought she would smile at the end of the night and walk right out back that door like it had happened so many times but she never did. She stayed with him that night, and for so many more nights later until eventually they had started a family.
Boy, you should have seen the look on Dean Winchester's face as he watched Tess give birth to their child. He may have had a tiny bit of a fainting issue but he fully recovered when the nurse handed him a blanket full of beautiful, yet crying, baby. Dean Winchester was able to stop the crying within seconds of humming his current favorite rock tune whilst carrying the baby over to her mother. Dean Winchester sat in the hospital bed with Tess and their daughter all night, leaving kisses all over both of his girls' faces.
It wasn't until 9 AM the next morning when visiting hours of the hospital had opened. Sam Winchester, who had fallen asleep in a waiting room chair while using his Earhart jacket as a blanket, finally had admission to step behind the door and see Tess and Dean's child. Dean Winchester held the baby close to his chest and whispered about how 'Uncle Sammy was gonna hold on to you for a minute.' He handed the baby off to his brother and watched, his eyes shining, as uncle and niece bonded. Dean Winchester was aware that Sam was going to protect the child just as much as Dean Winchester himself was going to.
