When Sam was six months old, his mother Mary (a retired creature hunter) was engulfed in a massive conflagration by yellow-eyed demon Azazel (one of four Princes of Hell).
Her Age. Because she is the mother of two grown men, it's easy to forget that Mary herself was only 29 years old when she was killed by Azazel; thus, she really only had the experience of a 29-year-old when she was resurrected, though she would have been in her 60s.
Mary was killed a few months after Sam was born in 1983. If you do the math, Dean is 37, Sam is 33, and due to the wiki Mary died at age 29. Meaning Sam and Dean are older then their own mother Mary.
Mary Campbell is a main character in The Winchesters portrayed by Meg Donnelly. "Mary is 19 years old and has been fighting the forces of darkness since she was a child.
When the Winchesters defeated Chuck, Sam was 37-years-old, and piecing together the montage in the finale of his remaining life puts his age at death to be around 65-70.
I love you so much. My baby brother.” He then makes Sam promise that it'll be OK, so Sam lays his hand over Dean's and says, “It's OK. You can go now.” “Goodbye, Sam” are Dean's final words as his hand drops and a tear rolls down his cheek.
Eileen Leahy - Sam's final love (Season 15)
Eileen Leahy (Shoshannah Stern) first showed up in Season 11's “Into The Mystic”, only to be killed a year later (“There's Something About Mary”).
It is revealed that she was killed because she interrupted the demon as he fed his blood to baby Sam. Sam learns for the first time that he was fed demon blood, and that Mary knew the demon that killed her.
He wishes it didn't happen. Dean is barely holding it together. He doesn't like that Jack is calling Mary's death, “the accident.” But he plays along and says they understand and they forgive Jack.
He is the couple's first child, four years older than his younger brother, Sam.
Before dying, John tells Dean, if he can't save Sam, he'll have to kill him, should he become evil. The fourth season episode "On the Head of a Pin" reveals that the demon Alastair tortured John in Hell for over a century, with John refusing the demon's offer to stop if he himself would torture someone else.
Season Eight begins with Dean Winchester returning from purgatory, where he was sent after defeating the leader of the Leviathan – ancient monsters and first residents of purgatory. Dean spent a year in purgatory before being able to escape with the help of his vampire friend, Benny, whom he met in purgatory.
When Jack killed Mary Winchester, he sought to redeem himself by creating new angels but it didn't help and he was locked away by the Winchesters. Jack escaped and roamed Earth before he was confronted by the Winchesters who intended to kill him but stopped.
Dean Winchester (deceased; soul exists in Heaven) - He is the oldest son of John and Mary, the older brother of Sam, and the older paternal half-brother of Adam.
Azazel aka the Yellow-Eyed Demon (Fredric Lehne) was the thing that killed Sam and Dean's mother; he was the thing that stood over Sam's crib and dripped blood into his mouth, turning him into one of his future soldiers; he was the reason the Devil's Gate opened; and he was the reason, ultimately, that Dean sold his ...
Emma was an Amazon conceived by Lydia and Dean during a one-night stand, unbeknownst to the latter. After trying to kill Dean, Sam shot her, killing her instantly.
Due to Jack being the son of Lucifer, Dean originally viewed Jack as a threat that had to be stopped from being born. After Jack was born, with Sam unwilling to kill him, Dean would keep an eye on Jack, threatening to kill him if Jack ever turned evil. Jack in turn sought Dean's approval and affection.
Season 12. Dean is both overjoyed and shocked to see his mother again, while Mary is confused and initially unaware who Dean is, since she remembers him as a 4-year-old boy. Mary attacks him and Dean is forced to reveal to Mary that she has been dead for 33 years, and that he is indeed her son.
Mary Winchester was the first death in the Supernatural TV series; however, in season eleven of the show, she was brought back to life by Amara, The Darkness. She was reconnected with her sons, Sam and Dean, and began aiding them in the family business, saving people and hunting things.
Targeted by Azazel, retired hunter Mary had the distinction of being the first character to meet her maker. The Yellow-Eyed Demon pinned Mary to the ceiling of baby Sam's room, slit her stomach, and eventually set her ablaze. Mary's gruesome demise forever scarred the Winchesters.
Unfortunately, though Mary did her hunters' blood proud, she fell foul of a temper tantrum from Jack Kline -- the Winchesters' Nephilim ward -- in Season 14. Jack accidentally banished Mary after losing control of his considerable powers, and her sons were unable to properly retrieve her intact.
Dean tells Lisa "you knew what you signed up for". Lisa replies, "I did, but I didn't expect Sam to come back". She knew their relationship was "over the moment Sam walked in the door", and tells Dean how weird his and Sam's relationship is. With Sam, Dean can never be happy.
In the end, Dean (Jensen Ackles) went out the way he always thought he would: Hunting. He was killed in the series finale while taking on a nest of vampires, but his ultimate end would come in the show's final moments, when he was reunited with Sam (Jared Padalecki) in heaven.
This one is a bit of a doozy, but the answer is yes. Dean accidentally conceived a child with Lydia, an Amazon who had a one-night stand with the Winchester brother in order to have a child. The child, Emma, was born two days after conception and grows up ridiculously fast.