In the series finale, after Dean dies, Sam leaves the bunker behind for good, taking their dog, Miracle, with him. Over the years, Sam has a family and a son, whom he named after his brother, grows old and dies of natural causes.
Emma Winchester (Daughter of Heaven and Hell)
Dean Winchester II, also known as Dean-O 2.0. and Son of Sammy, is a hunter and a member of the Winchester family of hunters. He's the son of Sam Winchester.
On September 30, 1862, in New Haven, Sarah married William Wirt Winchester, the only son of Oliver Winchester, the owner of the Winchester Repeating Arms Company. Sarah and William had one daughter, Annie Pardee Winchester, who was born on June 15, 1866 and later died on July 25, 1866 of marasmus.
John Winchester (Deceased) - Husband of Mary, father of Sam, Dean, and Adam Milligan.
Cassandra Masters is the daughter of Castiel and Meg Masters and the only known Nephalem to exist, which is a hybrid between a union of an angel and demon, even being part human due of Castiel and Meg's human vessels. Cassandra acts as one of the leading main characters with Sam and Dean.
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.
The first season of Supernatural featured some of the best monsters and moments, but one of the most personal plot points involved the introduction of Dean's first true love, Cassie Robinson (Megalyn Echikunwoke).
Lydia met Dean Winchester, along with Castiel at a bar. She shared a conversation with the Winchester and then went to her house where the two enjoyed a night together. Unknown to Dean, Lydia was impregnated with his child and in just a couple of hours, Lydia was already nine months pregnant.
Lisa Braeden is a single mother of one, who had a fling with Dean Winchester back in 1999, whilst he was on a hunt in the vicinity. She has a young boy named Ben who shares similarities to Dean, although she has categorically stated that he is not his child.
When Dean had first met Ben Dean considered the possibility that Ben might actually be his son. Lisa confirmed to Dean that Ben wasn't his son and his similarities to him was due to her 'type' that she hooked up with that Dean had fallen under.
Adam Millagan is a supporting character in Supernatural. He is the younger half-brother of Sam and Dean Winchester and the son of John Winchester. He appears as a minor character in season 4 and a supporting character in seasons 5 and 15. He also serves as the primary vessel for the Archangel Michael.
Dean is four years older than Sam and was always told from a young age to "watch out for Sammy". When a demon killed their mother, it was Dean who carried baby Sam out of the house.
As his relationship grew and grew with Lila, she accidentally got pregnant. Months past, without her telling him about the baby. Sam eventually wanted to break up with her after a couple of months. Lila talks to Sam about her baby as a ploy to make him stay with her and tells him that she wants to keep it.
Character Information
Millicent "Millie" Winchester is the second child of John Winchester and Mary Campbell, the younger sister of Dean Winchester, and the older sister of Sam Winchester.
Jared Padalecki proved that he might've never watched an episode of his own damn show in an interview with Variety. And like expected, it caused quite a stir for shippers who know in their hearts that Sam Winchester ended up with Eileen Leahy.
Finding that she has been gone for thirty-three years, Mary finally believes that Dean is her son and the two embrace. As the morning came, Dean and Mary say on park bench, with tears in her eyes, Dean begins telling her about John and how he sacrificed his life for Dean and raised he and Sam to be hunters.
Also she is forced to serve on patrol for a day and a suspect is able to get away because she ran while pregnant which incapacitated her and she had to go to the hospital but luckily did not get a miscarriage.
Pruitt Arike Miller is the daughter of Dean Miller and JJ Lau.
At Salute to Supernatural Vancouver 2022 Jensen further reiterated that Dean did not have romantic feelings for Castiel, saying that Dean saw Castiel as a family member and losing was like losing a brother.
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.
Supernatural season 15 controversially saw Castiel declare his love for Dean Winchester before dying.
Azazel eventually comes across Mary Campbell, the future mother of series protagonists Sam and Dean Winchester. After taking possession of her father (Mitch Pileggi), he kills her mother and stabs himself to kill his host.
Soon Dean receives Emma in his room and learns that she is his daughter while Sam finds that all the victims were killed by their own daughters. "The Slice Girls" is a reasonable episode where Dean has an Amazonian daughter after one night stand with an Amazon.
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.