Over 15 seasons, the Winchesters faced a seemingly endless array of powerful villains on Supernatural, so it only made sense that, at a certain point, they would come up with a team name.
Unfortunately, looking back at the Winchesters' final battle against God and how the series ended, Team Free Will has become a much darker and ironic reference. Supernatural follows brothers and demon hunters Sam and Dean Winchester who reunite to investigate the disappearance of their father and continue fighting evil long after that.
The Team Free Will nickname first originated in Supernatural season 5, episode 13 entitled "The Song Remains The Same." In the episode, angel Anna goes back in time to 1978 to kill John and Mary, so Sam will never be born, and in turn, Sam, Dean, and Castiel follow her to stop her plans.
However, their great rescue plan has a rough start as the time travel weakens Castiel to the point of total exhaustion. Looking over their pathetic team, Dean says: Well, this is it...Team Free Will. One ex-blood junkie, one dropout with six bucks to his name, and Mr. Comatose over there."
Although "Team Free Will" seemed like a hilarious and heartwarming name for Sam, Dean, and Castiel in Supernatural season 5, Chuck's plot twist in season 15 makes it horribly ironic and sad.
In Supernatural season 15, it is revealed that Chuck is not the uninvolved God he appeared to be but instead was the main villain all along. He constantly manipulated the Winchesters' lives for his own enjoyment and eventually became bored with them. At that point, he decided he wanted the universe to end.
In this way, the idea of "Team Free Will" is completely false. Where the Winchesters and Castiel believed they were fighting against the unfair powers of the universe in season 5, season 15 reveals that they were actually being moved around by said forces like pieces on a chess board.
This brings every choice the Winchesters ever made into question and creates a world in which the brothers didn't have to fight as hard as they did because many of their struggles never would have happened without God's interference. Therefore, Team Free Will is ironic because the name only came about because of Chuck's Supernatural God powers.
Fortunately, all was not lost for Supernatural's Team Free Will. Although Chuck had been manipulating the Winchesters all their lives, season 15 offered them a chance to actually become the "Team Free Will" that they had named themselves so long before.
While Chuck was pulling the strings back in season 5, now Sam and Dean actually had a chance to fight against the ultimate higher power and win free will not only for themselves but for everyone else in the world as well. In this way, Team Free Will became real.
In the end, Team Free Will does come true. During Supernatural's series finale ending, Chuck is defeated when Jack absorbs his energy during a pivotal moment between Michael and Lucifer.
By doing this, Jack becomes God and Chuck is left a human, stripped of all of his influence. From then on, Sam and Dean are free to live their lives without any universal power hanging over their head, and in fact, this scenario plays out fairly quickly as Dean is killed during a routine hunt.
Though Dean's death is tragic, it also proves that the Winchesters are now truly free to live (and die) like regular people.
Who Really Came Up With "Team Free Will?"
Considering Chuck's season 15 twist, the following question is inevitably raised: who really came up with the name Team Free Will? Based on Chuck's powers, it is entirely possible that he himself inserted the name into Dean's consciousness as a cruel and ironic joke, showing how, in some ways, Chuck was Supernatural's evilest villain.
On the other hand, Dean could also have come up with the name himself and Chuck, knowing everything he knows, would have certainly found it hilarious. Either way, the use of Team Free Will definitely has a deeper, darker meaning now that Supernatural has ended in the way it did.
Despite the ways in which Chuck changed the meaning of Team Free Will, the season 5 scene is still an iconic one that likely gives many Supernatural fans a sense of nostalgia.
Team Free Will evokes a feeling of heroism and determination that is admirable in the Winchesters but with an added hint of self-deprecation that anyone can relate to. Overall, the name emphasizes how Sam and Dean are always the underdogs, and yet they continue to fight for what is right because they never want to give up on the world and their right to be free.
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