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Supernatural: 20 Things Wrong With Dean Winchester That We All Choose To Ignore

Over the course of 14 seasons, Supernatural has had a lot of time to develop characters, for good and for ill. Naturally, no character can stay static for such an extended amount of time, especially in an hour-long drama. It is in the nature of the character to grow and change over more than a decade. Now, this isn’t to say that all the character changes are necessarily good ones. Sometimes a character’s growth can easily go south, not in the good Breaking Bad kind of way. For the most part, however, the main characters of Supernatural, especially brothers Sam (Jared Padalecki) and Dean (Jensen Ackles), developed in ways that make sense for them. Unfortunately, “largely” doesn’t mean “always.”

Sometimes, despite the dedicated fanbase, the brothers make some weird decisions or have traits that are less than amazing. As the eldest, it looks like Dean is going first as we dissect those traits. While Dean is an excellent hero and a good man, he doesn’t always make the best choices in life. That is fine-- no one wants a perfect hero, but in order to enjoy the character, there are some things fans overlook.

With that in mind, let’s go back, way back. We have almost a decade and a half of content to dig through here. Dean may be a Righteous Man, but he’s also a flawed one.

Here are 20 Things Wrong With Dean Winchester That We All Choose To Ignore.

20 He's Prejudiced Against Monsters

Dean has learned this lesson plenty of times over the show’s series. Just because most monsters want to destroy and maim others doesn’t mean that they all want to. When Dean comes up against a monster who just wants to live in peace and not cause any trouble, he doesn’t believe them, even though over the course of the series he’s met so many monsters who just want to live their lives.

Eventually, it becomes hard to get invested in Dean’s character in this type of scenario. He’s been involved in it so many times that he should know there are exceptions to the rule for monsters.

19 His Excessive Self-Loathing

For all of his self-confidence and charisma, Dean is actually full of deep self-loathing. Part of it comes from an unhealthy internalization of all the negative things that have happened to him since he was four years old. If something happens, even outside of his control, then it is somehow his fault. Dean Winchester seems to hate himself more often than not.

It can be seen in his deal with Michael. He was the one who had the Mark of Cain. He had to protect Sammy. A lot of these things were outside of his control to begin with. He didn’t have all the facts, was tricked, or was given a burden that he didn’t deserve. It’s rough to watch him continually blame himself for these things.

18 He Believed Others Over Sam

In the past couple seasons, the Winchester brothers’ relationship appears stronger than ever. It’s great to see because, for a couple of years, it looked like it would never really get repaired. There were secrets kept, soulessness ensued, and they experienced their first Apocalypse. The brothers were definitely not as close, and even estranged at times. Part of this came from the fact that Dean tended to believe others over Sam.

Sure, Sam lied to him about the demon blood drinking. Even so, there is still decades of history between the pair. Breach of trust aside, Dean should have given Sam the benefit of the doubt sometimes. It’s since improved, but it left a big black mark for the middle seasons of the series.

17 He's Overly Self-Sacrificing

This trait can definitely be laid at the feet of John Winchester (Jeffrey Dean Morgan) and his A+ parenting. Dean tries to sacrifice himself at the first oppotunity. One of the big examples of this is when Dean sells his soul to resurrect Sam at the end of season. He continues to see himself as worth less than others over the seasons. His life can easily be traded in order for them to survive.

It’s not really a great mindset for anyone to have. Sooner or later, one of those sacrifices will stick for Dean permanently. When others try to do the same thing, like Sam with sealing the Gates to Hell, Dean tries to figure out a way to subvert things. Yet he gets angry when Sam or others try to do the same thing for him.

16 He's empty inside

This was something that was brought up in season five and was never really mentioned again. When everyone was affected by Famine (James Otis) in the episode “My Bloody Valentine”, their appetites took them over. Dean, however, was the only one who remained unaffected by such desires. At first, it was because he said that he kept himself “well-fed.”  Famine, however, says that it comes from the fact that he’s empty inside after everything he’s been through.

It never comes up again in the show. That’s a pretty big bombshell to drop on a character without ever returning to it. It’s one of the more frustrating aspects of Dean’s characterization.

15 His Temper

Dean definitely has a temper on him. As stated earlier, part of it comes from his tendency to bottle things up. You can only get so far without needing to explode, like when he wrecks the Impala in season two or sends Castiel away in season nine. Not dealing with his emotions or his temper in a healthy way is not good for Dean. Sometimes, in anger, we say things that can’t be taken back. It leads to more of that tension between the brothers that plagued the middle seasons.

Eventually, it reached its zenith with the Mark of Cain. The Mark definitely took the anger in Dean and amplified it in a big way.

14 His Self-Medication 

Given the lifestyle that Dean leads, it’s not a surprise that the man drinks. There is definitely a marked difference in Dean’s drinking in earlier season and later seasons. The difference? The amount he imbibes. While he clearly is trying to cope with the trauma that has comprised most of his life, it’s also not healthy for him to do so.

To be fair, in recent seasons, Dean has toned things down. In times of stress, however, he tends to turn to the bottle more often than not. That can definitely lead to a troubling dependence on it that he can’t walk away from. Hopefully, it never gets to the point where Dean crawls into a bottle and stays there permanently.

13 His Attitude Toward Women

Supernatural's biggest glaring flaw is how it treats female characters. One of the more uncomfortable aspects of Dean Winchester’s personality is his attitude toward women. He objectifies and dismisses them. Dean doesn’t put a lot of stock in making long-lasting romantic relationships. The women that we can genuinely say that Dean Winchester respects can be counted on one hand.

Given the male-dominated culture of hunters plus a lack of a strong female role model growing up, it’s not surprising. It is definitely one of the more uncomfortable parts of Dean’s personality. Given the large female fanbase for the show, it would make sense to tone this stuff down.

12 Does He Want A Normal Life Or Not? 

Both of them Winchester brothers have flirted with the idea of living what Dean has christened the “apple pie life." After Sam threw both himself and Lucifer into Hell in “Swan Song”, Dean went to go have that sort of life. Though the question remains: why? He never showed interest in that life before that point in time. Since then, Dean has struggled with being a hunter and wanting that normalcy.

It comes up periodically, but the tension never really gets addressed. Eventually, Dean (or Sam) will return to the hunting lifestyle. The status quo is ultimately restored. If they will never stick to retirement, then why keep bringing it up? At this point, it’s just tired.

11 He Thinks Violence Is “Pure”

Dean grew up in a hyperviolent world. Whether it was “ganking” monsters or put through his paces as a soldier, the only language Dean even understood was violence. Violence against others and himself, it was how he learned to view the world growing up. It’s also, at times, the only way to communicate. Moments of big emotion for Dean tend to be mixed up with violent acts, such as destroying the Impala after his father’s passing or letting Samifer beat on him to reach his brother.

It’s no surprise that Dean has messed up view of violence and how it affects him. He sees it as something “pure” in the world. That’s honestly not a good worldview to have.

10 He Forgot Adam

Is Adam (Jake Abel) still in Hell? The answer is and seemingly will always remain: yes. After Sam dragged Adam/Michael, Lucifer, and himself into the Pit, we all are pretty convinced that's where Adam remains. As the seasons passed, Adam apparently has stayed there. He wasn’t resurrected. We have not seen him in Heaven. It looks like that both Dean and Sam forgot about him.

Sure, they didn’t have a relationship, but Adam was still kin. If Sam could not be resurrected but was stuck in Hell, then Dean would have done everything he could to get his brother elsewhere. He could have at least made a token effort to help Adam out, or at least mention him from time to time.

9 He Sold His Soul

One of the biggest plot threads of the early seasons was when Dean sold his soul to save Sam at the end of the season two finale. Not only did the brothers have a clock to run down, but a major thread was set up for the third season. The problem is, however, that Dean did the action for selfish reasons. He couldn’t live without his brother. Even though Sam himself would never want Dean to sell his soul for him, Dean did so anyway.

The gesture only makes Sam feel incredibly guilty and fuels his quest to restore Dean’s soul. That makes him easy pickings for those on the demonic side of things, ultimately culminating in him drinking demon blood.

8 His Mommy Issues 

The Winchesters both have astounding parental issues in general. John Winchester was abusive and did a psychological number on his sons. Neither brother ever really knew their mother, Mary (Samantha Smith), so at first, she was just a victim of the demon that destroyed their family. Her time as a hunter was only briefly touched on in the show.

When she was resurrected at the end of the eleventh season, it definitely showed a shift for the boys. Their mother wasn’t this perfect angel. She was a person with flaws and issues of her own to deal. Dean, out of the two brothers, took this revelation hardest. Technically, he was the one with memories of their mother and had a hard time reconciling things.

7 He Abandoned Sam

Dean and Sam’s relationship is the cornerstone of the series. While Sam went off to college, effectively abandoning his brother, Dean has done the same thing more than a few times over the season. In season five, Dean abandoned Sam after having a difficult time reconciling that Sam broke the final seal. In episodes focusing on his past, Dean is seen considering leaving the life behind for good. We honestly don’t see much of kid Sam in those episodes.

Dean has a habit of running when things get too real or hard, like when he told Cassie (Megalyn Echikunwoke) about the truth of his job or taking Lisa’s (Cindy Sampson) memories of him. He leaves when it gets tough.

6 His Amazon Daughter

Ben Braeden (Nicholas Elia) may not have been Dean’s biological son, but Dean definitely did, briefly, have a biological daughter: Emma (Alexia Fast). She was the child of Dean and an Amazon he had a one-night stand with. As an Amazon, however, Emma has to ritualistically terminate her father in order to inducted into the ranks. When confronted with his actual daughter, however, Dean tried to convince her that she could come with him. Emma wanted to destroy her father instead, leading to Sam ending her.

In the seasons since then, we haven’t heard any mention of Emma. She was Dean’s daughter and he clearly did want a relationship with her. It makes sense that there should be some remorse or regret over it.

5 He Broke the first seal

Sam gets a lot of flak for breaking the final seal and starting the Apocalypse. What gets glossed over, however, is Dean’s role in starting the end of days. As the Righteous Man, the first seal breaks when he willingly spills blood in Hell. Even though it was to stop his eternal torment, he did break that seal. He willingly spilled the blood needed to start the process.

That never really got touched on enough. Even though Dean did it under great turned, he still had a part in the beginning of the end. It doesn’t feel right to entirely place the blame on Sam.

4 He Let Gadreel possess Sam

Consent is key in angelic possession. They need to have their vessel agree for them to take over the body in question. Given Sam’s past with having his body used without his permission, you'd think Dean would figure that Sam wouldn’t like what happened with Gadreel.

The former guardian of Eden, Gadreel was a prisoner of Heaven who took possession of Sam’s body after he fell into a coma with Dean’s permission. Technically, it doesn’t make sense that Gadreel could do that given what we knew of angelic possession up to that point. It also takes Sam’s decision what to do with his own body out his hands. It’s a major violation of trust just because Dean refuses to take Sam’s own wishes into account. 

3 He Forms Unhealthy Attachments 

One thing that has been pointed out time and again with the Winchester brothers is their unhealthy codependence on each other. Given their childhood with John Winchester, it’s unsurprising that they felt like they could only depend on each other. Sam, however, more than proved that he could form healthy attachments with people, when given the chance.

Dean, on the other hand, just tends to sink into people and has a hard time letting go. He even puts them on pedestals, thinking they can do no wrong, and when they inevitably do, it feels like a betrayal. This is because keeps his circle almost suffocatingly small-- Sam, Bobby, Castiel, Charlie. When he forms bonds with people, he pushes all other attachments aside.

2 His behavior in Scoobynatural

“Scoobynatural” is definitely one of the best episodes of the later seasons for the series. It’s also just a flat-out amazing crossover episode. The Scooby Gang got more adult jokes while Sam, Dean, and Cas got to experience some childlike wonder. One of the most confusing aspects is Dean’s determination to keep the characters “innocent.” In the past, when dealing with people, Dean usually ends up being the one to break the news of the world of monsters and mayhem.

To see him so concerned with the innocence of fictional characters when he wasn’t so concerned with actual people in the past is disconcerting. Given the unusual circumstances, we can’t really blame him. It’s just a confusing course to see him take. 

1 His Mortality Has Lost All Meaning 

Given the number of resurrections over the years, the permanence of mortality has seemingly lost all meaning to Dean. Combined with his tendency to sacrifice himself time and again for the greater good, it feels like he does not care whether he lives or not anymore. We’re not suggesting that he wants to harm himself for good, but it definitely gets a little scary, especially with the level of self-loathing Dean experiences.

While he refuses to sacrifice his brother for anything, Dean is more than happy to give himself up. Maybe he hopes that someday, things will permanently stick. Even so, it just adds up over time psychologically and emotionally. Dean doesn’t care about his own life.

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What other problems with Dean do fans choose to ignore in Supernatural? Let us know in the comments!

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