Disclaimer: I do not own Supernatural or any of its characters.

Author's Note: I found this story in the backlogs of stories I started but never completed. I read through it, made a couple of changes here and there, and am working on cleaning up the ending. I decided to go ahead and post it. It will be about six or seven chapters long. I hope you enjoy it as much as I do.

Read and review please!!

Summary: A hunt goes wrong, landing both Winchesters in the hospital, one within an inch of death, the other regretting all the choices he has made. With help from an angel, Dean gets to see what would have happened if Jake hadn't killed Sam all those years ago in Cold Oak.

What Would Have Been

Chapter 1

It is never a good thing to hear the phone ring at one o'clock in the morning and hear a Winchester on the other end of the line. The phone call would ultimately end in someone getting hurt and nearly killed. One would think that after years of knowing the Winchester family, from young Mary before she met John down through the youngest, Sam, Bobby Singer would eventually learn not to answer his phone. But, he never did, not until April 19, 2009 when he was woken up at one o'clock in the morning by the shrill ring of the telephone and heard a Winchester at the other end of the line.

Bobby made it to the hospital in Duluth in record time, breaking all sorts of speed limits and out racing the cops on two different stretches of interstate to get there. He was in a foul temper as he slammed the door to his truck shut and tore off toward the ER of the small hospital. He hadn't stopped for a cup of coffee and he was missing his trucker cap. The latter was beyond belief, but it was the news that had come from a certain Winchester that had sent him into that rushing state that made him forget his trucker cap.

The waiting room for the ER was empty, save for one lone man who sat in the farthest corner away from everything. He had his head in his hands and he looked utterly defeated.

"Dean?"

The man looked up at Bobby, his normally bright green eyes dead with pain and sorrow. Dean looked horrible. He had a long, bloody scratch down one side of his face that stretched from his hairline to his chin. There was a bruise that shadowed one eye. His normally gelled and styled hair was matted with blood and sweat. He was favoring his left arm as he stood up to meet Bobby.

"Bobby, I'm glad you're here," Dean said. His voice sounded as if one were grating two pieces of sandpaper together.

"Are you okay?" Bobby asked as he placed a steadying hand on the elder Winchester's shoulder. The man looked as though one breath of wind would knock him over.

Dean slowly nodded his head, focusing on something that Bobby couldn't see. His entire body stiffened underneath Bobby's hand, and slowly, the elderly hunter turned to see what caused such a reaction in Dean.

There was a tall, grisly looking man with salt and pepper hair and spectacles standing in the swinging doors of the waiting room, a serious look on his lined face.

"Mr. James," the man said. It must have been Dean's alias, for he shook ever so slightly and crossed the waiting room to meet the man. Bobby followed close behind, curious to know what happened to Dean to make him react this way, but at the same time dreading the news he was about to hear.

"How's my brother?" Dean all but whispered. His face had gone from pale to white and he was still shaking. Bobby put a hand on his shoulder in attempts to calm him down. It did nothing.

"I'm Dr. Clapper," the man said ignoring Dean's question. "If you'd step into my office for a moment, we'll discuss Samuel's condition in private."

Dean's face grew impossibly whiter as he and Bobby followed Dr. Clapper down a brightly lit corridor and into a small, cluttered office with no windows.

"Have a seat," Dr. Clapper said gesturing toward the two folding chairs that sat on one side of the large desk that took up the majority of the room.

Dean did as he was told, swallowing audibly as he did so. Bobby kept a close eye on him as he sat down next to him, wondering what was going on and why Dean was reacting this way.

"How's my brother?" Dean croaked again. Blood seeped out of the wound on his face and dripped onto his already bloodstained collar, but he didn't seem to notice.

"Samuel is in critical condition," Dr. Clapper said gravely. "He has four broken ribs, a dislocated shoulder that we had to relocate twice, and a severe concussion, as you very well know."

Bobby listened attentively, wondering what had caused the sudden rush to the hospital. Though those things weren't exactly a walk in the park, it usually took a lot more than that to land a Winchester in the hospital.

"We're positive those things will heal in time," Dr. Clapper said. "It is the stab wound he received to his lower stomach that is the cause for the concern."

Dean's eyes closed and his face whitened even more, making the black circles underneath his eyelids stand out against his face, giving him a raccoonish appearance.

"Is he going to be okay?" he all but mouthed.

"Samuel has lost a lot of blood and is still losing it very rapidly despite our best efforts to close the wound," Dr. Clapper said removing his spectacles. "The weapon used to stab him also inflicted damage to his organs that is irreparable without extensive surgery, which Samuel is not up to at this moment. I'm sorry to tell you this, but you must prepare yourself. Samuel might not make it through the night."

Bobby felt his heart skip a beat at the horrible news. This could not be happening, he thought. Not to Sam. Granted the kid had been seriously messed up lately with the demon blood addiction and the constant rendezvous with that demon he was fond of, but no one deserved this.

Bobby was pretty certain that Dean was either unconscious or pretty close to passing out at that moment. There wasn't a muscle that moved in the younger man's body, except for the very rapid movements of his chest as he stared at the doctor in shock. An outburst was coming the second Dean could find his voice.

"Can we see him?" Dean asked finally. His voice was hoarse and there were visible, unshed tears in his green eyes, but he somehow managed to keep his voice steady.

"He's in ICU right now," Dr. Clapper said. "I'll show you the way, but I'm afraid its immediate family only. I don't want to put too much stress on Samuel."

"Bobby is my uncle," Dean said. "He practically raised me and Sammy."

Sammy. That was the first time Bobby had heard Dean call his brother that in a long time. Not since they had been reunited after Dean's four month stint in hell.

"All right," Dr. Clapper said with a nod of his head. "Follow me then."

They were led back down the brightly lit corridor and down another one to a small elevator. Dr. Clapper hit the 3 and the doors slid shut.

"Dean?" Bobby asked quietly placing a hand on the man's shoulder. He was worried when Dean didn't say anything, but just looked at him with an utterly defeated look on his face. Bobby had only seen that look on the oldest living Winchester's face once before, and that was when Sam had died back in Cold Oak, three years ago. It took a lot to scare Bobby, but the look on Dean's face scared the hell out of the older hunter.

The doors to the elevator slid open to reveal a dark, windowless corridor. Dr. Clapper led them to a closed door with a number 3 on it and paused.

"I don't think there's anything that could prepare you for what you're about to see," he said. "Sam's hooked up to a lot of machinery right now that's working to keep him alive. It looks pretty bad. And I'm not going to lie to you, it is pretty bad."

There was no sarcastic comment from Dean and that worried Bobby as much as the look in the elevator. There was nothing, nothing except the defeated look and a heavy sigh that Bobby felt more then heard.

Dr. Clapper pushed open the door and let Dean walk inside first. Bobby waited a few moments, debating whether or not to go get coffee or be there for Dean. He decided on the latter.

Dean stood frozen in the middle of the hospital room, staring Sam. Or at least, what Bobby assumed was Sam. There were so many wires and machines that it was impossible to tell where the machines ended and Sam started.

"Sammy," Dean whispered taking the last couple of steps forward and falling gracelessly into the hospital chair.

Bobby took a good look at the youngest Winchester, studying the too pale face that made the dark bruises stand out, the lines of pain even in sleep, the sling on his left shoulder.

"I'm going to get coffee," he grunted. It was going to be a long night. "I'll be back in a bit. You want some?"

Dean gave no indication that he had even heard the older hunter as he continued his silent vigil of staring at Sam.

Bobby sighed as he ran a hand through what little hair he had left. The sight before him was excruciatingly painful for myriad reasons. For one, he hadn't seen the Winchester brothers that close since Dean had come back from Hell. He hadn't see Dean care that much about Sam since he had come back from Hell. He hadn't seen Dean act like an older brother as of late. And it took Sam being critically injured for Dean to start acting like the older brother again. It took for them to be at the point of no return for Dean to start caring again.