Adam and John

The relationship between Adam Milligan and his father, John Winchester started in 2002 after John was made aware that he had a son by Kate Milligan. According to Kate when John learned he had a son, he raced to town and dropped everything to meet him.

2002-2004

When Adam and John first meet, Adam is at first weary of the meeting, having been excited at the prospect of seeing him, he now felt unsure about the meeting. However, the feeling soon vanishes when John hugs him and then takes him to a Minnesota Vikings game. After that initial meeting, John and Adam see each other about once a year. During one such visit that lasted at least through the weekend, John took Adam to meet his friend, Bobby Singer where Adam falls in love with a black Camaro. Bobby makes a deal with Adam that if he does work around the salvage yard, he'd pay him whenever he came and by the time he was sixteen, he'd have enough to buy the car from him.

Adam called John when his mother's boyfriend was hitting him. John urged Adam to take refuge with his grandmother until he could get to him. Adam agreed and when John picked him up, he and Adam went to Bobby's for a long weekend and by the time John took Adam to Windom, Kate had broken things off with her boyfriend for good. Later in spring 2004, John and Kate took a trip with Adam to Yosmite National Park in California. This vacation would be one of the last times that Kate, John and Adam would be together as a family unit.

2006-2008

Around October 2005, John gets a lead on the demon that had killed his wife, Mary all those years ago. He knows that the danger is really real this time and takes measures to protect those he loves from the danger. He disconnects his cell phone, making it impossible for his sons and Kate to get in contact with him. Unknown to him, Meg and several other demons were planning their revenge against John because of the fact that he had killed several of their "family". Meg is the one that suggests and eventually does, kill Kate in revenge, leaving Adam without a mother. When this happens, John is still unreachable and Dean and Sam are forced to care for Adam until they reunite with John after a shadow demon attack.

Recognizing that his brother and father were vulnerable with them, that John was weak around them, Dean urges John and Adam to separate from him and Sam and go their own way. John reluctantly agrees and he and Adam soon pick up a poltergeist case, where they save a pilot, Jerry, from certain death by ridding his house of the beast. In June 2006, John gets a call from his friend, Caleb, that John's friend, Daniel Elkins was dead: Murdered by vampires. The Colt gun, capable of killing any supernatural creature, was gone.

John does not want Adam going to Colorado with him and tries to drop him off with Bobby but Bobby is on his own hunt so John has no choice but to take Adam to Colorado with him to hunt the vampires. Adam is thrilled by this. When they arrive in Manning, they realize that they have picked up the same case as Dean and Sam, and the four Winchesters hunt the vampires together.

Adam is thrilled when, after discovering a trail to the vampire's hideout, John trusts him enough to stay by the truck guarding it. Adam stays behind like he is told but is soon interrupted by a woman he sees jogging up the road. She looks frantic enough that Adam leaves the safety of the truck and asks her what is wrong. She replies that her husband is missing in the woods. Adam follows her and ends up getting lead right into a trap. When John returns to the truck, he knows something is wrong and he and the boys immediately start looking for Adam. When they find him several hours later with a broken leg, they rush him to the hospital--where John, acting on Adam's pleas, goes back and kills the vampires while Adam is in surgery.

When he awakens, John and the boys head for Bobby's after he is released. John soon finds information on the demon that killed his wife all those years ago. He calmly talks to Adam, telling him that he's going to have to leave him with Bobby while he and Dean and Sam go check out the lead. Adam is scared of John leaving, he is still struggling with Kate's death and is desperate to never lose another parent again. Eventually, John gets his point across and Adam grudgingly agrees to not stand between John and the hunt.

John is devastated when Dean is killed after the demon possesses a truck driver to hit the Impala. For several days after, Adam only sees fleeting glimpses of his Dad who spends most of his time locked in Bobby's studdy or else in his room. Adam is stunned when Sam says that he blames John for Dean's death and reacts with anger to the accusation. About a month or so after Dean's death, Adam goes with John and Sam to find and kill the spirit of serial killer, H.H Holmes. Adam aides in the rescue effort when their friend, Jo Harvelle is kidnapped.

That September, John allows Adam to go home to Windom for his birthday. While there, John leaves early to go on a hunt with Sam that results in him getting thrown into prison for breaking and entering. When John arrives back home after a few days, they track down a few dead-end leads before John finally tracks a djinn demon. Adam is bored of being cooped up so against John's orders, he sneaks out and gets attacked by the djinn. In the alternate reality the djiin creates for them, Adam and John are still close but Adam's mother is alive and she and John are happily married.

After rescuing Adam, John grounds him before letting him off the hook early because of compliance and the fact that he hardly complained about his sentence. Shortly after, John gets a call from Jo saying that the Roadhouse had burned down to the ground, the blaze set by demons. John and Adam and Sam meet her at Bobby's house where they find out that Ellen is still alive, after being gone when the blaze happened.

Adam is there when John defeats Azazel for the last time. He watches as John puts a bullet through his head and is both stunned and relieved when Dean's ghost becomes the real thing. Adam is unsure it is Dean and asks him a series of questions that only the real Dean would know. When he passes the test, he and Adam wrestle around a bit before the reality of what had happened hits them: They were now about to become involved in an all-out war since the Devil's Gates were opened and demons released from hell.

They face their first real test when John, Adam and the two others meet Bobby and two hunter friends of his to face against the seven deadly sins. John and Adam successfuly against them before moving onto the next big hunt of theirs in Oregon: A violent spirit that had gone around murdering people, in his old life he had been violent, now as a spirit he was even worse. When the spirit ambushed Adam and collapsed his lung, John was horrifed to learn that Adam had to have a chest tube put in without the aid of numbing agents. He held his hand through the procedure while Bobby inserted it.