Gabriel knows a lot of things. He knows how to create people out of thin air, he knows how to turn back time. He also knows everything about the Winchesters. It was a must know subject in Heavenly Bible School.
As soon as the souls of Sam and Dean Winchester were created, everyone knew exactly what their fate was going to be. Lucifer knew, Michael knew, Father knew. They knew that Heaven, Hell, and Earth would come crashing down with the Winchesters. But no one knew how difficult it would be for them to accept their roles.
When soul mates are created, they are always fused together, and when they get their human vessels, they will always be born together. It is beautiful and simple. In most cases.
Gabriel watched as Dean's soul was born, and then Sam's. It was normal and natural, and Gabriel was tasked with his biggest mission since going to the Virgin Mary. He was to watch the souls, and keep them protected so they could fulfill their destiny, and when the day came for Dean Winchester to be born, all of Heaven watched in earnest. Gabriel prepared the bright soul, filling him with courage, so he could leave Heaven and start an exciting new life.
He only looked away for a second.
When he turned back, he was blinded with a great light, a light engulfing all of Heaven and making every angel startle. When the light dimmed, Dean Winchester's soul was bound together with another.
The other souls cheered in excitement while Gabriel and his siblings looked in awe. Soul mates had never been created like that before and It was troubling as much as interesting. Dean Winchester was to be born in a matter of minutes, and he would be forced to separate with his new-found other half. Other souls had to do the same thing, of course, but their guardians were always there to slowly prepare them for the devastating split. Sam and Dean Winchester had no counseling at all, and the abrupt separation would most definitely hurt them in their new life, especially Sam. He would be the most damaged. Gabriel sighed sadly.
"I am sorry, little soul."
The souls looked at him in confusion.
Why do you not rejoice, Archangel? They hummed. Look at what we have done! We will be so happy when we are born! Come and celebrate as we move on to our next life!
The other souls jumped and played in agreement, dancing and singing around the new soul mates. Gabriel shook his head.
"You will not be moving just yet, little soul." He spoke to Sam Winchester softly. "You are Dean's new soul mate, and you will reunite after he leaves. And you will be born with beauty and you will have a new life with him."
He hoped the souls believed his lie.
The Winchester's looked at him with anger, and Gabriel could feel the Heavens opening, ready to bring Dean to Earth.
You lie, Archangel! Look at us! We have fused and become one, and we will not be separated! We will be born together and we will be happy!
Gabriel watched as Dean Winchester was ripped apart from Sam, making his way down from Heaven to his new home. He screamed and fought the whole way, and Sam reached out for him, only to be pulled away by Heavenly forces.
When Dean was gone, the little soul wailed for days, Heaven shaking while angels tried to comfort the grieving Winchester.
Gabriel shed his first tear since he saw the creation of mankind.
When Gabriel saw the Winchesters as humans, their auras pulsing sadness, and explained their inevitable fate, he almost wept again.
He could see the damage to the broken souls. Especially Sam.