Supernatural had plenty of badass characters who would not be too much intimidated by the dark scenario of Squid Game. The dark fantasy drama has an abundance of supernatural beings, who will certainly have an added advantage through the games.
Even the human characters of the fantasy drama have gone through hell and survived in apocalyptic and post-apocalyptic situations. Hence, they too would fare much better than average humans in Squid Game.
Charlie
Charlie is a tech genius and her hacking skills are extraordinary. However, these skills will hardly be of any help in the Squid Game, which requires survival instinct more than anything. She became an equipped hunter on Supernatural, but she is too sweet for the dark and ruthless atmosphere of Squid Game.
Charlie will probably be one of the first ones to be targeted by the bad guys, especially in Red Light-Green Light. Also, she will most probably be killed trying to help the Winchesters as it happened in the show. The apocalypse-world Charlie, on the other hand, will be much more headstrong and will be able to retaliate better against the bad guys.
Bobby
Bobby is a skilled hunter and can get out of many bad situations. He cares about the Winchester brothers a lot and Bobby is a better father than John to them, which can be a reason why he dies in the Squid Game, to save them.
He may come far in the games due to his intelligence and knowledge. However, if paired with any of the Winchester brothers or any hunter he has known or cared about (like Ellen, Jo, or Rufus) in the Marbles game, he will deliberately lose so that his partner survives. His selfless nature will be the main cause of his death.
Crowley
Crowley is as cunning as they come. He has a habit of getting out of near-death situations using his intelligence and making deals with others. Therefore, this might be able to get him far in the Squid Game.
However, he can be soft sometimes and his affinity with the Winchesters might result in his demise. His own demons turned against him plenty of times, despite being the King of Hell because of this reason in Supernatural. So, it wouldn’t be surprising if his people in Squid Game realize that he is not fit to be a leader because of how he acted like a pet of the Winchesters and gang up against him to kill him.
Lucifer
Lucifer is the literal devil of Supernatural and his character resembles the character of Jang Deok-su a lot. He is extremely powerful, which will definitely aid him in many games. He is good at persuading people in joining his cause, but he is ready to throw them away like trash when they are of no use to him.
This selfish quality of Lucifer can lead to his death. Near the end of the games, many people will realize that he used them for their own. As a result, they might try to push him in the Glass Tile game or try to kill him in some other way.
Rowena
Rowena is even more wickedly clever than her son, Crowley. It was a full-circle moment that she took her son’s place by the end of the series and became Queen of Hell. In Squid Game, she will know how to play tactfully and her survivor instinct will keep her alive.
Rowena is a reminder of Han Mi-Nyeo from Squid Game. Rowena is someone who will do anything to exact her revenge on people who betrayed her or humiliated her, just like Mi-Nyeo. Thus, she might be the one to take down Lucifer with her in the Glass Tile game because Lucifer has made her life hell many times on Supernatural.
Castiel
Castiel from the early seasons was a force to be reckoned with. He was extremely powerful, he could teleport anywhere and he could kill anyone with hardly any effort. These powers would have aided him a lot in Squid Game. However, after being cut off from heaven, his powers started diminishing and by the end of the series, he wasn’t as powerful as he used to be.
Still, Cas is not someone who could be killed easily. He is intelligent, agile, and a survivor, who has fought and won against many great opponents. He would win the early games quite easily. But, if the Winchesters’ lives are ever at risk, especially Dean, Cas would give his life readily to save them. His main objective would be to ensure Sam and Dean remain alive instead of saving his own life.
Dean
Dean is one of the best monster hunters and he has survived much worse conditions than in Squid Game. He has been to Hell, Purgatory, and the apocalypse world. He has been tortured brutally plenty of times. So, it is a no-brainer that he will be able to survive through all the games. Also, Cas would probably sacrifice himself to save Dean and that will work in Dean’s favor to win the games.
Cas would probably sacrifice himself to save Dean’s life and that will make him go on to the next level. Similarly, other characters like Bobby, Crowley, and Charlie’s deaths would also help in Dean’s survival in the games. However, his own weakness comes down to his younger brother Sam, who Dean would do anything to protect.
Sam
Just like Dean, Sam has also a lot of people who would gladly give their lives in order to save him (like Bobby, Cas, Crowley, even Rowena). Sam is smart, brave, and doesn’t back down no matter how bad the condition is. He has suffered through Lucifer’s tortures, fought against heaven and hell’s most powerful beings.
Sam is always the one who is giving hope to his brother, Dean, and urging him to continue the fight without giving up. So, his fearless and confident nature would work in his favor to win the Squid Game.
Chuck
Chuck was the omnipotent God, who could do anything with a simple snap of his fingers. He might not even have to make an effort in any of the games in the Squid Game. He could just snap his fingers and reality would bend to his will.
Chuck created infinite universes and destroyed them. So, winning the entire Squid Game would be a piece of cake for him. Chuck is a lot similar to Cho Sang-Woo because he might seem a helpful person at the beginning of the games. However, as the Squid Game progresses, he will show his true colors and would turn against anyone and even kill them to get his way.
Jack
Jack is the new God in the Supernatural world and he is now the most powerful being in the universe. Even before that, he was immensely powerful, being the Nephilim. He has brought Cas back from the Empty using just his mind and even killed the apocalypse-world archangel, Michael.
Jack was the one who defeated the then-God, Chuck, at the end of season 15 of the show. He sucked all the powers of God. He has gone through many difficult situations but is always able to come out of them. Moreover, he is a kind-hearted being. Like Gi-hun, he will win the Squid Game without deliberately killing anyone and will use his winnings to help others.
