The Supernatural prequel, The Winchesters has started filming its pilot episode and the show is set to be narrated by Dean. Dean Winchester is one of the heroes of Supernatural, who has saved countless lives. However, that doesn't mean that he is perfect, far from it. He has a penchant for making poor decisions and endangering himself and the people around him.
Dean is a hot-headed and impulsive man, who often doesn't think things through before making a decision that is likely to affect a lot of lives. Many people in his life, as well as others, often have to pay the price for his bad decisions. One may admit though that his poor decisions kept the show going for 15 seasons.
Pointing The Gun At Sam
Dean has always been overprotective of Sam, willing to do almost anything to save his brother. Due to this, it came as a shock to many fans of the show when Dean pointed his gun at Sam in season 15.
Here, Dean is not thinking straight. Sometimes, he can get carried away when he gets too focused on the mission. However, this was a bit too much, even for Dean. Sam is just trying to stop Dean from pushing Jack to his death, but Dean won't stop at anything to get rid of Chuck and get his free will back, so he points the gun at Sam.
Killing Amy Pond
Dean killed Amy Pond, who was a Kitsune, but also an old friend of Sam. It can be argued that he is a hunter and his job is to kill dangerous monsters and Amy had murdered some homeless people, so she wasn't innocent.
However, going behind Sam's back to kill her was not a great decision on Dean's part. Amy was Sam's friend and Dean should have done Sam the courtesy to make him understand why Dean needs to kill her. It's funny how both brothers would rather betray one another and cause a major rift between them later on rather than talk about things beforehand.
Selling His Soul To Save Sam
Talking about his overprotectiveness and co-dependency on his brother, Dean went to some extreme lengths for Sam during the entirety of the show. At the end of season 2, when Sam is killed, Dean feels like he failed as a brother. So, he sells his soul to a crossroads demon to save Sam and then goes to Hell for 4 months and is brutally tortured there.
Any normal loving brother would be heartbroken after seeing their sibling die in front of them, but being willing to go to Hell to resurrect the said brother is not a healthy coping mechanism. This also shows how little he values his own life and doesn't stop to think that how Sam would have to live with the fact that his brother went to Hell for him.
Erasing Memories Of Lisa And Ben
One of the worst qualities of Dean is that he thinks he can control the lives of people around him and he justifies it by doing it for their good. At the end of season 6, Dean asks Cas to make Lisa and Ben forget about him.
This is just outright cruel and akin to playing with someone's life. Dean spent a year with Lisa and Ben and he has no right to alter someone's memories like that, for whatever reason. They have essentially lost a year and they will never know the reason why. Even Sam immediately calls Dean out on this and says it is one of the most messed up things he has ever done.
Kicking Out Castiel
It's no secret that Castiel has given up a lot for Dean. However, somehow whenever Cas needs something from Dean, he lets him down almost every time. This is one of those times when Cas had lost his grace and so he was human for the first time and not to mention, homeless and incredibly confused about everything.
Dean, rather than helping his best friend, kicks him out of the bunker onto the streets. Yes, he had his reasons, but he could have explained that to Cas and helped him in some other way like putting him in a motel or something. What he did to Cas is not how one should repay people who have sacrificed so much for them.
Letting Michael Possess Him
For a world-renowned hunter who stopped many Apocalypses, Dean sometimes can act extremely stupid. He let an archangel possess him, knowing that archangels can never be trusted. In the early seasons, viewers learned that Dean is the Michael Sword, the true vessel of archangel Michael.
So, in season 13, when he said yes to Apocalypse-world Michael take control of his vessel, he should have figured out that Michael would never let go of his true vessel so easily. What followed was that Michael locked Dean in his mind and committed horrible acts being in his vessel.
Taking On The Mark Of Cain
Despite Cain's constant warnings, Dean was adamant about taking the Mark of Cain from him. The Mark is supposed to lock the Darkness away and whoever bears it becomes the ultimate killer. Dean took it on to kill Abaddon.
Unfortunately, this proved to be one of the worst things to happen to Dean. The Mark is the world's first curse and it turned Dean into a mindless, aggressive killer. Things got so bad that he almost killed his best friend, Castiel. It eventually led Dean to become a Demon and then later on unleashing the Darkness upon the world and condemning everyone in the universe.
Tricking Sam To Say Yes To Gadreel
Dean's overprotective nature can cross too many personal boundaries and this is another instance of that. Sam was at the brink of death at the end of season 8 after the trials, and Sam had accepted his death. However, Dean couldn't let that happen and he tricked Sam to say yes to an angel called Gadreel (Ezekiel) possess him.
Sam trusts his brother more than anyone in the world and Dean betrayed his trust by lying to him, manipulating him, and letting an angel take control of his body without his permission. This is not just a violation of Sam's trust but also his body and mind. Later, Sam is mad at Dean due to this, and rightly so.
Blaming Cas For Mary's Death
Jack lost his soul in season 14 and killed Mary by accident. When Dean got to know about it, he blamed Cas for Mary's death and pushed him away. It was a cruel thing to do to Cas, especially when he lost Mary too, who was his good friend, and then also lost his son, Jack.
At such a time of severe loss, Dean and Cas could have helped each other out process their grief. Instead, Dean irrationally blamed Cas for everything and made both of their lives ten times worse.
Willing To Harm Jack Multiple Times
Dean and Jack have had a perplexing relationship in Supernatural. Sometimes, they acted like the ideal father-son duo, and other times, Dean was ready to kill Jack. It seemed like the writers weren't sure about their relationship dynamic. When Jack was born, Dean had wanted to kill him because he blamed him for Cas' death.
When Jack lost his soul and accidentally killed Mary, Dean wanted to lock him in Ma'lak Box for eternity and later on in the season 14 finale, again Dean planned to kill him. Thus, this willingness to harm someone he claims is his son is appalling. After more than a decade of character development, viewers expect Dean to not act like his own father.