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Supernatural: 10 Times Dean Winchester Was A Jerk

The dynamic on Supernatural has been where Sam is the sensitive younger brother who thinks about what to do before he does it, and Dean who is the older, more brash brother who prefers to let his actions do the talking.

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Because of his aggressive attitude, there have been dozens of occasions where Dean has been a jerk, and even his most loyal fanbase will have a hard time in explaining why he acted the way he did. In order for you to understand what we mean, here are 10 times Dean Winchester was a complete jerk on Supernatural.

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10 Every time he punched Sam

Up until the 10th season, there had been at least one instance in every season where Dean had punched Sam out of nothing but frustration. This wouldn’t even be a soft punch; Dean would unload everything on Sam, proven by how Sam would bleed whenever the punch had landed.

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Since he’s the younger brother, Sam would never hit Dean back, but that doesn’t cover the fact that it’s a total jerk move to use your little brother as a punching bag. Dean’s reasons to do so would range from annoyance that Sam was possessed, losing an argument, or just because he was concerned Sam wasn’t around.

9 Killing Amy Pond And Not Apologizing For It

Dean’s justifications for killing have always been skewed toward how he feels about someone rather than it being totally for good reasons. Case in point was when he killed Sam’s childhood friend for being a monster; she was guilty, sure, but Dean didn’t see her worthy of redemption and stabbed her in view of her young child, leaving the boy parentless. 

Later on, he and Sam would have a falling out over this, but Dean would never apologize for betraying his brother and leaving a child as an orphan. Making it worse was how Dean would then become pals with a vampire the following season, and this time it was Dean who attempted to justify letting Benny live.

8 Trying To Kill Kevin's Mom

In the second episode of season eight, the Winchesters and Kevin found themselves at an auction where supernaturally powered beings had their abilities removed, rendering Crowley vulnerable to harm. By the end of this episode, Crowley had possessed Kevin’s mother, and Dean gave chase.

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Rather than consider that he was in the process of killing Kevin’s mother if he killed Crowley, Dean would almost succeed in slitting off the woman’s throat until Kevin distracted him. We’ve seen an instance where Sam was similarly possessed, but Dean wouldn’t harm the demon because his brother was in there; meaning he was fully aware Kevin’s mother was in there and just didn’t care if he killed her along with Crowley.

7 Not Understanding Sam's Reasons For Consuming Demon Blood

The entirety of season four had the Winchester brothers at odds over Sam’s secret practice of consuming demon blood in order to power his supernatural abilities. The angels were purposefully vague in telling Dean what Sam was doing was wrong, leading Dean to judge Sam as if he were a monster.

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Sam was clear that he felt he was helping people by using his powers, but Dean would never take even a moment to listen to Sam; instead, he would be openly hostile to him, either punching him or threatening he would hunt Sam down if he were to go dark side. It could have all been avoided had Dean not had a bullying kind of mentality over this.

6 Solely Blaming Castiel In Season 6

Castiel had his eggs in several baskets during season six as he saw the civil war escape his grasp. This led to him making a deal with Crowley in order to open up Purgatory and consume its souls so he could take out Raphael.

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When the Winchesters found out about this, they instantly blamed Castiel as if he had malevolent intentions. Dean, in particular, was openly hostile toward Castiel, even telling him it changed nothing when Castiel saved Lisa’s life. Whenever Castiel tried to make Dean understand, Dean would simply turn him away and place Castiel in the same light as Crowley and Raphael.

5 Leaving Adam In The Cage

After finding out they had another brother, the Winchesters initially tried to get him to their side, but Adam ended up becoming Michael’s vessel. After Sam sacrificed himself to the Cage, Michael (and Adam along with him) was taken to Hell as well. 

In season six, Dean had a sho to bring Adam back from the Cage by requesting Death to haul him back but instantly chose to get Sam’s soul instead. While Dean had limited options at the time, there’s no denying there have been times where he could have rescued Adam. Basically, Dean just hasn’t bothered to try and rescue his brother because he has no attachment to the boy.

4 Not Sharing Hell And Purgatory Experiences With Sam

For some reason, Dean figured Sam wouldn’t understand what he went through when he was trapped in Hell and Purgatory. He would be vague about what had happened, leading Sam to become distant to him both times due to Dean purposefully leaving stuff out to talk about.

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He never saw it from Sam’s point of view that Sam needed clarity over what happened and couldn’t very well just sit back and accept that Dean was back without any explanations. As a brother, he should have given Sam the right of being family and shared with him everything that had happened.

3 Treating Castiel Like A Disposable Friend

Whenever push comes to shove, Dean always looks to shove Castiel aside. We’ve seen this every time Dean and Castiel have disagreed on something, and each time Dean is ruthless in the way he talks to Castiel.

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Very recently, Dean openly told Castiel he would kill Jack, despite Castiel being the guardian and basically the father of the boy. After Dean had Jack trapped in the Malak box, he ignored Castiel’s anger at having sealed Jack up and didn’t even think Castiel was worth the time of day — at least if Dean had explained to Castiel the reasoning behind what he did, he wouldn’t have come across looking like a jerk.

2 Being A Jerk In General

If you really think about it, Dean’s base personality is being pretty much a jerk. He’s obviously not a bad guy, but he’s definitely not modest or compassionate as Sam or Castiel are. In any situation, Dean is the one who is aggressive and non-trusting, and he bosses Sam and Castiel around on an everyday basis.

Whenever there’s an argument, Dean never listens to what anyone has to say and his word is final. If new characters are brought into the mix, Dean is not the guy who starts on a friendly basis, and he looks to get these people out of his hair until they prove themselves to him.

1 Trying To Kill Jack

As we mentioned before, Dean was in full mood to kill Jack in season 14, and this was taken to such extreme lengths that he was pretty much out of character during this point. Despite knowing that Mary was a fool who goaded Jack into accidentally killing her, Dean treated Jack as if he murdered Mary.

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Thereafter, he would imagine many scenarios where he took Jack’s life, and ignored Sam and Castiel completely when they justified that it wasn’t Jack’s fault at all since his soul was gone because Dean had been the one to let Michael in him in the first place — Jack had used his soul to kill Michael and save Dean. You can’t come across as a bigger jerk when you try to kill the person who saved your life.

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