Jeff was over at Nick's house, the eight year olds playing Mario Party and laughing when they lost of one of the mini games. It had been two years since Dean had left. He still called as much as he could and made sure to come around on Jeff's birthday. He was in the middle of winning Bumper balls when Nick's mother called for them. They paused the game before running downstairs, giggling as Jeff almost fell. They had dinner and Jeff stayed the night. Bobby picked him up the next day. That was the last Nick saw of Jeff that summer.
Dean had come home. He had come to tell Bobby about John missing and that he was going to Stanford to find Sam, and that he was taking Jeff with him. Jeff felt excited about finding his uncle. Sam had never let Jeff down and the blond missed him. They left and Jeff found the comfort of the impala surround him. It was home. He had grown up in this car and he was happy to be with his dad again. The ride was filled with Jeff telling Dean about school and stuff he and Bobby had done. Dean ignored the pang in his chest. They made it to Stanford late at night. Jeff was asleep and Dean didn't have the heart to wake him. So he went in to get Sam alone. It wouldn't take long…hopefully. He was right though. Sam agreed to come for the weekend, needing to come back so he could make an interview for law school. Dean was proud of his brother. Jeff woke up when he heard the impala trunk slam closed. He heard his dad tell someone to be quiet. Jeff heard hushed arguing but was too tired to keep up. He got out of the car and looked at the trunk. He smiled and hugged Sam. "Sammy!" He heard and felt his uncle chuckle. "Hey buddy. " Sam hugged him close. He had missed his nephew dearly and wanted to slap Dean for leaving him. He had kept up with Jeff through Bobby and was beyond pissed that his dad would make Dean do that. He was going to make sure Dean never did it again.
They didn't find John and Sam ended up staying with them. He seemed sadder than the day he had joined them, but Dean and Sam wouldn't talk about it in front of Jeff. Dean assured him that it would all be okay and that his uncle just needed some time.
School came back and Jeff found himself once again dropped off at Bobby's, his dad and uncle going off on their hunt for John. Jeff and Nick didn't have class together this year, but they still spent as much time as they could together. Nick didn't ask questions about where Jeff had been or why he looked sadder than normal. He trusted the blond to tell him when he was ready. He figured home life for Jeff was bad. He hadn't seen Mr. Winchester in awhile and he knew Jeff missed his dad more than anything. It was the middle of the school year when Jeff started feeling different. He was now nine and in third grade. While other guys were talking about cute girls in other classes, Jeff couldn't care less. He only wanted to hang out with Nick and it seemed like Nick felt the same.
There was one girl in his class named Lucy. She had curly brown hair and nice blue eyes. She followed Jeff around and Jeff found to love her presence. When Nick was gone he would hang out with Lucy. One day she kissed his cheek. He didn't feel anything except a sisterly brother bond. That night he kissed Nick's cheek. It wasn't a brotherly bond. It was something more but Jeff would never tell anyone.
The next time he saw his dad was at his grandpa's funeral. Dean had come home a mess and hadn't let Jeff go for the longest time. Jeff didn't mind. He missed having his dad hug him. His dad and uncle stayed at Bobby's for awhile. Dean spent his days fixing up the impala that had somehow wrecked. Jeff knew something was up but no one would say it. Sam tried to keep Jeff entertained while Dean dealt with the death of John. Every night found Jeff sneaking into Dean's bed, waking up from a nightmare where he would lose Dean.
Dean would drive Jeff to and from school every day. It was a nice time for Jeff, having his dad around and not worrying about his dad in any danger. He didn't know if his dad was in any immediate danger but the arsenal in his dad's trunk said a different story. He didn't want to ask though, too scared of what the answer might be. Some weekends Dean and Sam would leave to work, coming back soon and never leaving Jeff alone at Bobby' for too long. At the end of the year Sam and Dean left for awhile. Dean promised to be back before the summer so Jeff didn't get too upset about it. It was a few days till May when his dad came back. He told them that Sam had gone missing. So they took off in the impala. Jeff was left at motel rooms while his dad and Bobby tried to find Sam from sources. They sent them to a ghost town. It was dark and Jeff walked closely behind his father. Before he knew it, Dean was yelling his brother's name and running towards his uncle. Bobby ran after another guy and Jeff stood frozen not believing what he had just seen. He couldn't understand why someone would want to hurt his uncle. Sam was the best and no one should want to hurt him. Bobby came back and Dean carried Sam inside a building. Bobby led Jeff inside too, making sure to keep him away from Sam and Dean. They stayed there until morning, Jeff not moving or speaking. Bobby took him on a food run. He got Jeff some ice cream hoping to give the boy something sane to hold onto. When they got back, Bobby and Dean argued. Bobby took Jeff home that day. A few days later his dad and Sam came home. Bobby was surprised and then there was more arguing.
Jeff and Nick were 10 and leaving elementary school when it happened. Jeff disappeared without as much as a goodbye. He went to the blonds' house to try and find him. Bobby said his uncle had taken him away for awhile. Nick never saw him again.
Jeff's world had changed so much. His dad was dead and he was living on the road with Sam. Sam had told him everything, about demons, vampires and other monsters. He showed Jeff how to shoot a gun and how to fight. Jeff slowly fell into the hunter life that his father tried so hard to keep him away from. Sam taught Jeff school things and hunter things. He joined Sam on easy hunts. Other times his uncle left with this girl that Jeff didn't trust at all. Her name was Ruby and he had heard his dad mention her before. No one but Sam trusted her. She was a demon after all. Jeff didn't understand his uncle's friendship with her, but Sam was his only blood family left. He couldn't lose him too.
It had been four months since Dean had died. Sam tried his best to raise Jeff and make sure he had a somewhat normal life. Ruby had told him not to worry and that Jeff would be fine. He was a Winchester after all. Sam still kept things from Jeff as best he could. They were currently in a motel near where Dean was buried. Sam was on a demon lead and had Jeff hang out at the motel. Jeff was used to being left alone now. He wished he was in school right now, able to see Nick and sleep in his room with no knowledge that monsters existed. He wanted his father back. He wanted a normal life but that wasn't going to happen. He was in his motel room when he heard knocking. He stood from the bed and went to open the door, revealing Sam and Bobby. "Jeff." He was engulfed in a hug before he could question it. His dad was here. He was hugging him again. Jeff had questions, they all did, but the main part was that Dean was back and it was really Dean. Not a monster that Jeff would have to watch Sam kill. Dean was pissed when he learned what Sam had been up too and that he had dragged Jeff along for the ride. He eventually settled down once he accepted the fact that Jeff wouldn't be able to be a kid forever. With the life of a hunter, nothing stayed secret for long.
Bobby had a friend that could tell them what pulled Dean from hell. Her name was Pamela and she was a force to be reckoned with as Jeff soon found out by her attitude. She said she could contact whatever had brought Dean back, but that it might be dangerous. Any monster could have pulled him out and making contact with them was something they shouldn't take lightly. Dean made Jeff wait in another room. Jeff tried to argue, but Dean wouldn't have it. He left Jeff then with a shotgun and some salt rounds. He didn't show it but it broke Dean's heart seeing the blond with a gun. Jeff stayed in the other room until his dad rushed out with s crying Pamela. Sam stayed with Jeff at the house. He explained that Pamela had gotten hurt by someone named Castiel. He also said that was who pulled Dean from hell.
Pamela ended up losing her eyesight that day. His dad felt horrible about it but it was done. There was no going back. There was only forward and finding whatever it was that had done this. They were currently at a hotel. Jeff and Dean asleep as Sam sneaked out to meet Ruby. That's when the screeching began. Both Dean and Jeff covered their ears and avoided the braking glass from above. It soon stopped. Bobby came back and they left, Dean talking about finding the thing and ending it and leaving Sam out of the plan. He'd only try to stop them.
The whole thing took place in an abandoned farmhouse. They painted every symbol they knew and got ready for a possible attack. The summoning spell was said and they waited. Soon the place was shaking and the roof seemed like it was going to fly off. Lights exploded and sparks started flying. Dean pushed Jeff behind a table as the barn doors flew open and a man walked inside. Jeff stared at the familiar man. He hadn't seen him since he was six and his dad had left him at Bobby's. He had sworn it was just a dream. A sign any little kid would dream up as reassurance that his dad still loved him and hadn't abandoned him to be raised by someone else. Bobby and dean shot the man but nothing happened. "Who are you?" "I'm the one that gripped you tight and raised you from perdition." Dean stabbed him with the demon knife but it was useless. The man just looked amused as he pulled the knife out. Bobby tried to hit him but the man stopped him and then did something to make him fall asleep. "We need to talk…alone" Dean's eyes snapped to the table where Jeff was hiding. He moved to keep the things eyes from noticing.
"What are you?"
"I'm and angel of the lord." Dean didn't buy it for a minute. An Angel wouldn't have burned a pour woman's eyes out. He didn't get time to find out what the guy was. Lightning struck and the shadows of wings were stretched from the man's back.
"Some angel you are. You burned that lady's eyes out."
"I told her not to spy at my true form. It can be overwhelming to humans. So can my true voice but, you already know that. " Jeff couldn't help but drop the gun he had been holding when he remembered the screeching. He saw Castiel turn and Dean run in front of the table. "I'm not here for the boy Dean. I'm here for you. We have work for you."
After that night, the Winchesters desperately tried to stop the seals of the apocalypse from being broken. Of course they failed with Sam being controlled by Ruby. Lucifer was set free, along with the road to the apocalypse. After that they tried to find a way to kill the devil, a hard thing when the only way to kill him is by Michael's hand. Not to mention Dean and Sam being the vessels. It took Sam saying yes and sacrificing himself into the cage, to save the world. Dean was broken up about it. He stopped hunting and moved into an apartment. Dean got a job at a local garage and Jeff did online schooling. It was easier staying at home where the salt and silver knives were. Sam eventually came back, and when Dean denied the invitation to start hunting again, Sam left. Joined the Campbell's and hunted with them. He still kept in touch, `not as much as Dean liked, but he couldn't complain. Jeff had a normal life now. It wasn't perfect, but it would do.