WARNING: Re-edited. Also, spoilers for the season 3 finale, season 5 finale, and season 7's first few episodes.
Author's Note: Just a little something that popped into my head. I guess it takes place at the start of season 7, although it references times before that too.
Disclaimer: I don't own Supernatural.
The first time since Karen's death that Bobby's whole world came crashing down around his ears was on May 15th, 2008, because that was the first time he lost both his boys.
In one predictable yet unbelievable moment, Dean was ripped from his life by demonic hounds. Violently murdered for the soul he had sold while saving his younger brother's life.
Sam…Well he was lost the moment his big brother died. He stuck around just long enough to quietly help Bobby with the burial, and then he was gone off to who-knew-where.
By May 16th 2008, Bobby's house was oddly empty and his heart was completely hollow. Everything he'd held dear was taken from him and he was left alone to face the dark road ahead.
It would be several long months of steady alcoholism and barely keeping it together before Dean would return and Sam would come back.
The second time Bobby's world fell apart, it was for similar reasons.
Sam trapped Lucifer inside of himself and dove head first into the deepest pit of Hell for all of eternity. He saved the entire planet, but at a price Bobby hated having let him pay. Sam was gone forever in a cage with the Devil.
Although Dean had lived through the ordeal in Stull Cemetery, his green eyes were devoid of all their previous light. He parted ways with Bobby a couple of days after Sam's death to go fulfill the promise he made his little brother to have a normal life.
For all Bobby knew, both his boys had been stolen from him yet again and the odds of recovering any sense of happiness in his life were basically non-existent.
He had no reason to know that in a little over a year he'd have them both back.
The last time Bobby's world was attacked by misfortune, it was when the Leviathans set fire to his house.
He had come back to his salvage yard that night to find practically everything he owned burning brightly against the night sky. His books, photos, and less valuable worldly belongings were all toast. Every object he possessed was annihilated in a brilliant display of oranges and yellows.
But though his house went down in flames, his home did not.
Because this time was different.
Sam and Dean were both still alive and kicking, and in the cabin that had once belonged to his good friend Rufus Turner, Bobby was settling in nicely with his boys.
Sure, Dean's leg was broken and he whined from morning until night about how bored he was, and yes, Sam's head was full of screws threatening to come loose at any moment…
But they were both there with him, bickering and breathing still. The world was on the verge of utter disaster for the third time in as many years, but not his world.
Not his boys.
For that reason, Bobby believed everything would be ok.
Secondary Author's Note: Thanks for reading! Feedback is greatly appreciated! :)