|“||Two salty hunters, one half-angel kid, and a dude that just came back from the dead, again. Team Free Will 2.0||”|
Team Free Will is a nickname made up by Dean after time traveling back from 1978 to 2010.
The nicknames were based on Sam's former demon blood addiction, Dean's intentional lack of education, and Castiel's state of unconsciousness, as a result from time traveling.
Dean did not use the name of this team for a number of years, though he continued to fight for free will and object any outside force that tried to control him or his teammates.
In 2017, when Castiel began to doubt his own importance, Dean reminded him that he, Sam and Dean were members of Team Free Will.
After Castiel's resurrection, Dean declared Team Free Will 2.0 to be "two salty hunters, one half-angel kid and a dude who just came back from the dead, again." Following the rescue of Mary Winchester and Jack from Apocalypse World, Team Free Will 2.0 are seen hunting werewolves together, indicating that they became a full-time hunting team following their reunion. Months later, they worked together on a regular gorgon hunt with the help of Rowena MacLeod.
However, Team Free Will 2.0 is broken when Jack accidentally kills Mary Winchester in his soulless state. Jack becomes hunted by the Winchesters, particularly Dean, for his actions and the threat he poses. After Dean refuses to kill Jack, Team Free Will 2.0 stands up to God himself, only to have God kill Jack and unleash chaos upon the world in retaliation for their defiance. The remaining members, with the help of Rowena MacLeod, Arthur Ketch and the demon Belphegor, manage to stop God's plan, but the remainder of the team is broken when Castiel chooses to leave due to Dean's anger towards him and inability to forgive Castiel. The remaining members are later reunited after Dean makes amends with Castiel during a mission to Purgatory to get a Leviathan Blossom to trap God.
Team Free Will 2.0 (Seasons 13-15)
Team Free Will 2.0 allies/non-official members
- Gabriel (as of Unfinished Business; deceased)
- Rowena MacLeod (as of Funeralia; deceased)
- Mary Winchester (as of Exodus; deceased)
- Alternate Bobby Singer (as of Exodus)
- Alternate Charlie (as of Exodus)
- Lucifer (temporarily in Exodus; deceased)
- Arthur Ketch (as of The Thing; deceased)
- Garth Fitzgerald IV
- Eileen Leahy
- Maggie (deceased)
- Jody Mills
- Donna Hanscum
- Claire Novak
- Kaia Nieves
- Annie Jones
- Patience Turner
- Alternate Kaia Nieves (deceased)
- Belphegor (as of Back and to the Future; deceased)
- Adam Milligan
Original Team Free Will (Seasons 5-12)
Original Team Free Will allies/non-official members
- Gabriel (deceased)
- Jody Mills
- Donna Hanscum
- Bobby Singer (deceased)
- Crowley (deceased)
- Rufus Turner (deceased)
- Kevin Tran (deceased)
- Charlie Bradbury (deceased)
- Benny Lafitte (deceased)
- Balthazar (deceased)
- Garth Fitzgerald IV
- Season 5
- Season 6
- Season 7
- Season 8
- Season 9
- Season 10
- Season 11
- Season 12
- Season 13
- Season 14
- Season 15
- The reason for the name may be because Michael, the team's enemy, opposed free will as he told Dean prior to sending him back to the present.
- Two of Team Free Will's original three members have been possessed by Lucifer. However, Lucifer has appeared as all members at least once.
- Two of Team Free Will's original members have been possessed by Crowley.
- Two of Team Free Will's original members have been possessed by an angel and a demon at the same time.
- Two of Team Free Will's original three members have killed a primordial entity.
- Two of Team Free Will's original three members have killed an archangel with the help of an outside source of power.
- Each of Team Free Will's original members have died and come back to life.
- Each of Team Free Will's original members has time traveled.
- Each of Team Free Will's original members have been sent to Purgatory.
- Each of Team Free Will's original members has killed a member of law enforcement.
- Each of Team Free Will's original members have used The Colt but only Sam and Dean have killed beings with it.
- Each of Team Free Will's original members have met God.
- Each of Team Free Will's original members has killed a main antagonist.
- Each of Team Free Will's original members have been possessed by an archangel.
- Sam was possessed by Lucifer in Swan Song in order to lock Lucifer back in his Cage.
- Castiel was possessed by Lucifer from The Devil in the Details to We Happy Few in order to battle The Darkness.
- Dean consented to possession by Alternate Michael in Let the Good Times Roll in order to gain the power to finally kill Lucifer.
- Each of Team Free Will's original members have held control of themselves while possessed by an archangel.
- Sam seized control back from Lucifer to send Lucifer back into Lucifer's Cage.
- Castiel seized control from Lucifer when Lucifer tried to kill Sam, but could barely hold Lucifer back from killing Sam and did not have the strength to expel him. Lucifer later restored control to Castiel willingly for a brief period of time in We Happy Few.
- As part of his deal with Alternate Michael, Dean held control of his body after consenting to possession by Michael. In this state, Dean was powered by Michael and used several of the archangel's powers to fight and kill Lucifer. Michael then betrayed his deal with Dean and took full control of his body. Dean later seized back control again and kept Michael imprisoned within his own mind for months.
- Each of Team Free Will's original members was responsible for the death of a Prince of Hell:
- Each of Team Free Will's original members have served as a major antagonist, with Soulless Sam and Demon Dean serving as secondary antagonists for Season 6 and Season 10 respectively, and Castiel serving as a main antagonist for Season 6.
- In the Season 13 finale Let the Good Times Roll, Team Free Will 2.0, minus Castiel, accomplished the original team's goal when Dean killed Lucifer with the help of the Alternate Michael.
- Three versions of Zachariah have been killed by a member of Team Free Will. The Main Universe Zachariah was killed by Dean Winchester in Point of No Return and the Apocalypse World Zachariah was killed by Jack in Good Intentions. In Lebanon, Sam killed the alternate timeline Zachariah.
- Three members have died at least once in a season finale.
- Dean was killed by a hellhound in No Rest for the Wicked. He was resurrected by Castiel the first time he died. He also died after being killed by Metatron in Do You Believe In Miracles? and subsequently came back to life as a demon due to the Mark of Cain.
- Castiel died for the first time when Raphael used Molecular Combustion on him off-screen in Lucifer Rising and again in Swan Song by Lucifer, but was later resurrected both times by God. He died again in All Along the Watchtower when Lucifer stabbed him with an angel blade but was resurrected in The Big Empty by the the Shadow.
- Jack died in Moriah when God smote him. He was resurrected by Billie.
- As of the Season 13 episode The Big Empty, each of Team Free Will's original members has faced another version of their character.
- Dean faced a demon version of himself in Dream A Little Dream Of Me and a future version in the apocalyptic universe in The End.
- Sam faced two versions of himself in The Man Who Knew Too Much, his Soulless self and a version who retained his memories of Hell.
- Castiel faced and killed his alternate counterpart in Exodus.
- As of the Season 13 episode Tombstone, Jack is officially a member of the team.
- Also, through his induction two of the four members are related: Sam and Dean are brothers while Castiel and Jack are uncle and nephew.
- As of the Season 13 episode The Bad Place, all members of the Team Free Will 2.0 have visited the Apocalypse World.
- As of the Season 13 episode The Bad Place, all members of the Team Free Will 2.0 have killed an angel.
- As of Byzantium, all members of the Team Free Will 2.0 have died and come back to life.
- As of Ouroboros, three of Team Free Will 2.0's members have killed an archangel.