The kindest and most compassionate Winchester in Supernatural It has always been Sam, who did not have the level of explosive emotions as his brother Dean. However, it is Dean who has had more friends than Sam, due to his more outgoing nature and forming connections with others on his adventures.
But that doesn’t mean that Sam didn’t have genuine friends of his own, with more than several noteworthy names. Since Bobby was his surrogate father and Jack his surrogate son, these relationships do not qualify as friends as they were family members. Likewise, love interests fall into the romance category, leaving the characters Sam had a friendship with based on trust, chemistry, and lasting impact.
For a few years, Sam and Crowley had a much better relationship than the latter had with Dean, as Crowley had even confessed his need to be loved by Sam in a moment of vulnerability. They continued to help each other in later seasons, although this weakened due to a number of factors.
This mainly had to do with Sam trying to take Crowley’s life when Rowena commissioned him to do it in exchange for a favor. After this, although Crowley somehow overlooked what Sam did, their “friendship” was based on mutual assistance rather than Crowley feeling a connection with him as he did with Dean.
In his own way, Gabriel truly cared for Sam, and the latter’s influence allowed him to grow as a character. Gabriel connected with Sam as well as the younger brother, along with the burden of responsibility that fell on him.
Gabriel trapped Sam in his time cycle to make him see that he needed to leave Dean, even allowing Dean to be resurrected simply because Sam asked him to. Sam also didn’t blame Gabriel the way Dean did for leaving heaven, as he understood what it was like to feel trapped between family.
8 Amy pond
This is a relationship that Sam should have stuck with, as Amy ended up taking other people’s lives when her monstrous tendencies got out of hand. Amy did not officially become Sam’s romance, as things never took off once Amy had to kill her mother to save him.
They reconnected their friendship in the future when Sam covered up for Amy after she had to kill people to feed her son. The reason this friendship is so remarkable is the fact that Sam parted ways with Dean after discovering that the latter had killed Amy, which means that he valued their friendship so much that he parted ways with his own brother.
7 Kevin Tran
Due to all the times the Winchesters didn’t help Kevin when he needed it, there are enough reasons not to consider them friends. However, Sam and Kevin always had a close relationship when they were on the same page, with Sam being the one who commiserated with Kevin’s plight as a prophet.
Dean tended to ask too much of Kevin, while Sam was the one who was nice to him and listened to his problems. Kevin had also considered Sam to be a better friend than Dean, although Sam’s decision not to search for Kevin after Crowley captured him would certainly have been on Kevin’s mind.
For a long time, Sam considered Sully a figment of his imagination, not realizing that he was a Zanna dedicated to bringing 9-year-old Sam the comfort of a friend. After thinking that Sully wasn’t real, Sam ordered him to leave so he could grow up.
Decades later, Sully returned to Sam’s life, where the latter apologized for his earlier behavior. Sully proved that he still knew how Sam felt inside, as the two of them instantly reconnected, this time with Sam appreciating all the help Sully gave him as a child.
5 Charlie bradbury
Fans generally wanted the original Charlie to return for season 15, as the alternate version didn’t make much of an impact. However, regardless of who Charlie was, Sam always managed to make her her true self and not use the history of the alias she had.
Charlie became a sister figure to Sam as he shared his problems with her to which she provided answers. He confided in her in his plans to find a way to cure Dean of the Mark of Cain, which he did to the point of losing his life.
4 Garth Fitzgerald IV
Unlike Dean, who found Garth annoying, Sam was always willing to indulge in his display of affection. Sam also regarded Garth as a valuable ally without ever making him feel less. His compassion for Garth was such that he did not care when Garth turned into a werewolf.
Garth appreciated Sam’s friendship so much that he named one of his sons in his honor – Dean was not given this honor. It was clear that Garth felt safe around Sam, as Sam liked Garth for who he was and sympathized with his problems.
3 Jody mills
Jody was one of the few who treated Sam and Dean exactly the same, being a combination of mother figure and older sister. In turn, Sam was there to comfort her after the loss of her husband and resurrected son.
Their friendship was so strong that Sam could show up unannounced and expect to be treated like family, and Jody’s cooked the only “home cooked meal” the kids had. Jody also ended up becoming a complete hunter thanks to training provided by Sam alongside Dean.
two Rowena MacLeod
Because she started out as an antagonist, Rowena got worse in some ways. However, she became so much better where it mattered most, all thanks to her growing relationship with Sam. By the end of Rowena’s life, Sam had easily become her best friend.
After initially forcing her to help, Rowena softened her willingness to become an ally and joined Sam so many times that she also trained in witchcraft. Her fated death at her hands broke Sam’s spirit as she acknowledged Rowena’s claim that they had truly loved each other very much.
Their relationship was always so sweet that fans have dubbed them “Sasstiel”. With the reveal that Castiel had a crush on Dean, it means that he considered Sam his real best friend. In fact, their relationship was much better than Castiel and Dean’s, as Sam never created a conflict with Castiel.
Sam also had no other friends who approached the level of trust and constant contact he had with Castiel, and he instantly forgave him for his part in Mary’s death. When Dean broke off his friendship with Castiel in season 15, Sam actively tried to get him back. Of course, Castiel valued Sam so much that he went straight into Lucifer’s cage to retrieve Sam’s soul.
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