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Supernatural: 5 Times Dean Was A Villain Against His Will ((& 5 Times He Did It All On His Own)

Sam and Dean Winchester are riddled with issues and problems that oftentimes help put them on the villainous side of the moral tightrope. Over fifteen seasons of Supernatural, Dean makes many mistakes and bad choices that, while usually being done with good intentions, end up causing more harm than good and paint him in a bad light.

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There are also times, though, where Dean's actions may be evil but are out of his control. This could be due to him being possessed, being in hell, or being affected by the Mark of Cain, and had Dean really been Dean; he would have done half the abhorrent stuff he did during those times.

10 Being Overly Aggressive & Murderous Was Against His Will

When wielding the Mark of Cain, Dean slowly but surely morphed into a different character, one with more anger, aggression, and more vicious murderous tendencies, far removed from the Dean fans know.

The way he killed Abbadon was genuinely shocking; his over-aggression and enjoyment in pummelling on her dead body was quite the sight. There is then murdering Claire's 'friend' Randy and the thug debt collectors out of pure bad blood. The general itch to kill Dean holds while imprinted with the Mark of Cain is scary, but there is no doubt it was not truly Dean; he was being controlled by the mark. Cain, in one of the few instances where villains held the moral ground, did warn Dean about the mark, he did not listen.

9 Constantly Lying To Sam Was His Own Doing

One of the classic Supernatural go-to tropes and storylines is Sam or Dean lying to the other brother about something that usually does not need to be lied about, leading to a drama, a fight, and some brotherly forgiveness.

Most of the time, when Dean lies to Sam, it is unnecessary and inspires a sigh from audiences. It is not inherently evil to lie, but it does lead to awful things like Kevin Tran's death when Dean keeps secrets like Gadreel's possession from Sam and does not make Dean look like a hero.

8 Breaking The First Seal Was Against His Will

The 66 Seals to free Lucifer from Hell were a significant part of season 4, and the main goal of Sam and Dean in the season was to prevent Lilith from breaking it - not realizing she herself was the final seal. The first seal was just as important, though.

A heartbreaking piece of information that comes out during the season is that, while in Hell after his heartbreaking season 3 death, Dean actually broke the first seal and set the events of season 4 in motion by torturing a soul in Hell. This is a strange one; on the one hand, Dean was conscious and aware, but on the other hand, there is nobody alive who could claim to survive such incredible torture without giving in to Alastair's offer of torturing rather than being tortured. Dean hated himself for it, but nobody really blames him, considering he was in hell for forty years.

7 Casting Out Castiel Was His Own Doing

Dean allowing Gadreel to poses and heal Sam's body led to some awful things. Not only did Sam pretty much hate Dean for a time, but Gadreel killed Kevin, and Castiel was thrown out of the bunker by Dean like garbage.

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It is bad enough that Dean shunned his best friend at the behest of the angel he was hiding in his brother, but he did so at a time when Castiel was extremely vulnerable; he was a human. Castiel was forced to take up a new identity and try to figure out life as a human on his own, betrayed by his best friend with no good reasoning.

6 Killing Cyrus Styne Was Against His Will

The Styne family were not a great set of villains, but they made a big impact during their short time on the show, killing Charlie Bradbury and helping show off the full ferocity and cold-blooded nature of Dean with the Mark of Cain.

After escaping their home and killing every single member of the family brutally, a blood-stained Dean found his way back to the bunker where three Styne brothers were attempting to destroy the brother's home. One was Cyrus, the youngest Styne brother who hated his family and wanted no part of their evil, begging Dean for his life so he can go live quietly. Dean shoots him in the head before beating Castiel half to death. Dean Winchester would have probably let Cyrus go, and he certainly would not have nearly killed Cas; the Mark of Cain took its toll on Dean's temperament in a big way.

5 Betraying Amara Was His Own Doing

Dean's relationship with the Darkness, Amara, is a strange one that fans still cannot quite wrap their heads around. What fans do know is they cannot hurt each other; they can apparently betray one another and get the other killed, though.

Despite agreeing to help them deal with God, Dean's plan to recruit Amara was actually one to use Jack to kill the pair of them. This hurts Amara incredibly, who is absorbed by Chuck as a result. It was definitely a questionable decision by Dean, they actually had an ally against God who seemed to prove she did not want to cause chaos and pain on Earth, and he betrayed her.

4 Becoming A Demon Was Against His Will

Demon Dean, affectionately dubbed Deanmon by the passionate fandom, was a short-lived but iconic time in Supernatural that provided some great moments and some of Dean's evilest times in the show.

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Becoming a demon was not Dean's choice. It was a by-product of the Mark of Cain refusing to let him die after Metatron killed him. As a demon, Dean was brash, violent, and murderous, almost killing Sam before he was cured. The Deanmon story may not have reached the heights of its iconic first scene, the season 9 cliffhanger when Dean opens his black eyes but seeing Dean like this was a great inclusion to the show.

3 Killing Amy Was His Own Doing

Amy Pond was an old friend of Sam who happened to be a monster, a Kitsune, who had popped back up again, killing people to feed her son. Sam kindly let her go, believing in her ability to be a good person as she had been in the years prior.

Dean did not have such faith. He went to the motel where Amy was staying and killed her in front of her son, who Dean threatened to kill should he feed on humans. It is one of the worst things Dean does in the show and is arguably his most unlikable moment, with no provocation or possession or Mark of Cain compelling him to do so.

2 Everything Michael Did In Dean's Body Was Against His Will

Other than variations of Dean such as Deanmon, Jensen Ackles did not really get to play other characters in Supernatural before season 14 when he got to show off his skill as Michael, who had possessed Dean.

In Dean's body, Michael experiments on monsters and attempts to use them to conquer the Earth. He toys with Dean, making him believe he is in control of his own body when, in fact, Michael is still in there. Dean was forced to watch on as Michael did heinous things around the planet, similar to how Sam had to watch on while possessed by Lucifer and Meg.

1 His Treatment Of Jack Was His Own Doing

The fourth and newest member of Team Free Will, Jack Kline, made a huge impact in his three seasons on Supernatural and formed some great relationships. His dynamic with Dean, though, was hated by fans for a long time.

That is because Dean pretty much emotionally abused Jack, telling him he was a monster, admitting he wanted to kill him, threatening him on multiple occasions. Dean even threatened to kill Sam in order to use Jack to kill Chuck and Amara. There is then the brother's heartbreaking betrayal of Jack to put him in the Ma'lak box. The two are OK in the end but never form a bond like Dean and Cas, Jack and Cas, or even Sam and Jack, and fans find it hard not to hate Dean when he treats Jack the horrible way he does.

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