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Dean Winchester Endures the Worst to Keep the World Going

I started watching Supernatural in college, and instantly I was entranced by the story of the Winchester brothers. Years and years of episodes have allowed audiences to get to know them quite well over time. I like Dean and Sam equally, albeit for different reasons as the two couldn’t be more opposite.

I wanted to explore Dean because I find him the more complex of the two. For a psychology course I took in college, I had the option of exploring a character of my choosing and discussing how they exhibited traits of the Big Five; naturally, I chose Dean. Remembering that assignment inspired me to go further in depth into the life and personality of Dean Winchester.

A Kid With Lots of Issues That Makes the Best of It

Dean wasn’t handed an “apple pie life,” as he would say. Early on, he was cursed, beginning with the tragic loss of his mother, Mary. As a child, he carried his infant sibling Sam from their home as the house, with Mary inside, perished. From then on, he was tasked with the heavy responsibilities of looking after his younger brother and helping his father John in his quest for vengeance. John coped with the tragic loss of his wife by turning into a hunter of the supernatural, swearing revenge on the thing that had killed Mary and training his sons like soldiers from then on. Dean and Sam were swept up into a life they never asked for, and a lifestyle they would later find out their mother had never wanted for them.

Young Sam and Dean sitting on a bed, Sam looking down and Dean looking at Sam, with one lamp lit in a dark motel room in Supernatural

Dean was more of a parent than older brother to Sam. Dean never had a real childhood, and while he could have been resentful of that, he instead chose to give Sam the childhood he never had, for as long as he could. That speaks volumes for his character and his selflessness. He and Sam had many good times together, and in a way, Dean got to experience childhood through Sam. They carved their initials in the back of their dad’s (and later Dean’s) beloved 1967 Chevy Impala, affectionately nicknamed “Baby.” In many ways, that Impala was their childhood home, making the car that much more special, and that’s probably one of the reasons why Dean cherishes the vehicle so much.

While Sam rebelled, Dean didn’t. I’ve always thought it was because he wanted to be seen as loyal and good enough in his father’s eyes. Dean more than proved his capabilities to John, but it was like he kept having to prove himself, as long as his father was alive. Even after John’s death, Dean still acted like he had something to prove, maybe most of all to himself.

Dean’s relationship with John was complicated. He obeyed John’s every order and unlike Sam, didn’t pursue his own dreams, instead remaining in the wayward and twisted “family business” to help John fulfill his sworn vengeance. It’s selfish on John’s part to want his sons to search for their mother’s supernatural murderer, not only because it doesn’t allow them to live their own lives, but also because it places them both in unspeakable danger. As it was, Sam, though he was out of the “family business,” suffered for it with the death of his girlfriend in the series pilot.

Dean wearing a leather jacket and looking to his left with Sam standing behind him looking solemn and staring in the same direction as Dean in Supernatural

Dean wanted John to succeed in finding and killing the thing that had murdered Mary, but even at 26, the age Dean was when the series began, he was still taking orders from John as though he were a child. Why would Dean put up with that, having legally been an adult for nearly a decade at that point? He says it’s because he held respect for his father, but I’ve always wondered if it was out of fear. If Dean were to stray away or defy John in any way, maybe he feared being cut off as Sam was. Family means everything to Dean, especially with the loss of his mother, whom he was close to. Having felt like he’d lost Sam, he held onto the one person he had left, dysfunctional tendencies be damned.

Dean is the glue in the family. He played mediator more times than he’d probably care to recall between a feuding John and Sam, keeping the peace as best he could. That constant stress and pressure, which worsened as Sam got older and more rebellious, and John became more desperate and controlling, is nothing short of a toxic environment. That had to have taken a toll on Dean’s mental health and sanity. He never really got a break from it either, if flashbacks and the recollections from Sam and Dean are anything to go by. Yet, he always stood by Sam, and John, trying to see the situation from both of their perspectives.

While Sam’s departure may have solved the constant fighting between him and John, it caused a whole other slew of problems that Dean appears to struggle with to this day. He makes bitter comments about Sam leaving him and John for college from time to time, signifying that maybe he’s never really gotten over that major blowout and the repercussions thereof. Since Dean isn’t one for “chick-flick moments,” however, he’s never really vocalized or talked through that experience from his perspective with Sam, which might ease some of his internalized pain.

Dean looking distraught in Supernatural with a split lip and bruised eye

Dean doesn’t talk about things. Not in the way he should. As a result, he’s got years of pain built up inside, whether he knows it or not. Worse yet, it’s pain that he could have otherwise worked through and healed from had he just said something.

I’ve always thought Dean was more like Mary than John. That’s a good thing in many ways. He’s the one that keeps the Winchesters together, he’s who Sam confides in, and he’s the family’s rock. Sometimes it drains Dean, but it also gives him strength, knowing he’s helped someone, especially his brother.

Adulthood and Fighting for Good

As Dean grew up, he continued developing into a caring and thoughtful protector. He’s not perfect, but he does things no one else does, or can. He’ll save complete strangers, holding himself to high standards. In “Sam, Interrupted,” Dean admits that he has to save everyone. If even one person dies, he considers it a massive failure, and he takes that burden on for himself. He holds himself to high standards, and if he fails, he holds himself strictly accountable. Dean is his own worst enemy in that way.

Dean would rather take on everyone else’s pain than to see them endure it, and maybe also because he’d rather face their pain than face his own. He’s definitely earned the “World’s Best Big Brother” mug for all he’s done for Sam, especially at the end of Season 2 when Dean struck a deal with a demon to bring Sam back from the dead (the first time Sam actually died on the show), sacrificing his own well-being without a thought. Now, Dean wound up going to Hell for his brother. He suffered dearly, as he was tortured, and was forced to torture others in his time there, until he was brought back from the dead himself. He’s proven over and over that he’ll do anything to save Sam, even if it’s to his own detriment. While noble, it’s also frightening, and somewhat selfish.

Dean Winchester looking angry and intense holding a gun in his hands in Supernatural

Dean is afraid of being alone. Plus, because he feels it’s his job to look out for Sam, he feels he has failed and it’s up to him to fix it when Sam is killed. Part of why he brought Sam back was because he didn’t want to be the one Winchester left behind. As Sam is brought back, he comes to realize what it means for Dean that he’s alive once more. That’s a tough thing to live with, given his life means Dean’s impending death. It ultimately changes Sam, who loses some of his innocence in the process, given the guilt and hardness he acquires from wanting to be tough like Dean, knowing his brother will soon be gone.

Dean doesn’t see it that way, however. It’s simple: he brought his brother back because Sam couldn’t die. Not on Dean’s watch.

The thing is, Dean doesn’t have a high opinion of himself. It’s sad, really, that he doesn’t acknowledge he matters just as much as everyone else. It’s been pointed out here and there on the show, by Bobby, and also via Dean’s admittance to Jo in the Season 7 episode “Defending Your Life,” in which he says to her ghost that he’s “90 percent crap.”

Dean hasn’t had an easy life, and it’s obviously severely affected his mental health and opinion of himself. Ultimately, however, Dean doesn’t let anything get to him so deeply that he can’t function or keep moving forward. Yes, he has his moments where he declares he’s done and the world can basically implode, but he bounces back even in his worst moments because he’s not a quitter, and despite everything, he somehow manages to find faith amidst despair and light among darkness.

His ability to see past the darkness is admirable, especially when he’s seen and experienced the worst that darkness has to offer. Perhaps he would’ve been happier with a significant other at his side, and I was definitely onboard with the shipping of Dean and Jo—they seemed perfect for each other, but had the worst timing, and ultimately, Jo was tragically killed, along with most of the friends and family of the Winchesters.

Dean and Jo staring sadly at one another in Supernatural

Though much heartbreak is on the show, Dean manages to pull several forms of comedic relief, most notably with his frequent pop culture references. Sometimes inappropriate or ill-timed, they’re still funny because it’s Dean, and only Dean can make them work in those moments. These references can annoy Sam or whoever else is around, but for audiences, it’s a welcome break. Plus, I definitely love Dean’s taste in classic rock music (I’m a fan myself), and his music is a welcome addition to any episode. In a show like Supernatural where most of the storylines are dark, even gory on some occasions, we need some comic relief and good music somewhere.

One of my favorite examples of Dean’s comedy is “Yellow Fever.” Dean becomes terrified of absolutely everything, albeit gradually, after he’s exposed to a “ghost sickness.” The endless fear is so unlike Dean that it only amplifies the hilarity of the entire situation, even with Sam and Bobby racing against the clock to find a cure and save Dean’s life. A cat jumping out of an old locker with Dean screeching in terror is unforgettable, which is why it’s one of the most memorable scenes from the show. I’ll miss moments like that when the series officially ends.

Dean has tried for a normal life, but like Sam, doesn’t seem to have much luck with it. Both he and Sam are consistently and constantly pulled back into the hunting life, against their will, because the world is headed for disaster and requires their saving.

Despite having seen death and destruction in abnormal volumes in his lifetime, even experiencing death himself on multiple occasions, Dean still remains human in the best ways. He is compassionate, especially with kids. He still cares about every single person on Earth, wanting to save them all. He hunts and saves the world because people are obviously not lining up for the job. He still fights for Sam, despite Sam’s betrayals in the past, and has gotten his brother through everything, especially Sam’s addiction to demon blood, of all things.

Dean hugging Sam with a sad and relieved look on his face in Supernatural

Though it killed Dean to lock Sam in Bobby’s panic room to detox, he did what he thought was best. Sometimes that’s a good thing, and sometimes it leads to clashes with others, especially Sam, because if something isn’t done Dean’s way, it means the highway. Dean is a natural leader, assuming control where he feels control is needed, and steering whoever is on his side to victory, his only goal to restore the well-being of the world and its people.

Dean has many coping mechanisms for dealing with his line of work. Some are healthy, some aren’t. But it’s what works for him. Yet, since the addition of Cas, it seems Dean’s life has improved, as he and Cas have become best friends, bordering on brothers. It doesn’t suck to have someone like Cas on your side—especially on the battlefield.

I don’t know what kind of ending is in store for Dean, but I’ve always wanted him and Sam to have some kind of peace in the end, to experience a level of happiness previously thought impossible for the Winchesters and to have some kind of joy restored to make up for all the tragedy they’ve had in their lives. Maybe Dean finally gets to have a family and drive “Baby” to vacation destinations instead of hunts.

Yet, knowing the nature of Supernatural, it seems more likely that Dean, along with Sam, would go out fighting. That’s how Dean would want it: to go out swinging. If that’s the case, I hope he gets the best version of Heaven possible; the guy deserves the best the afterlife has to offer.

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Written by Kacie Lillejord

Kacie is a freelance writer versed in various forms. She loves pop culture, screenwriting, novels, and poetry. She has previously written for The Daily Wildcat, Harness Magazine, Cultured Vultures, and Screen Rant, with 25YL being her newest writing venture.

2 Comments

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  1. I lapsed watching Supernatural after they killed off one of my favorite characters, but I’ve probably seen most of the episodes anyway because my wife loves the show, and more importantly, Dean. Can’t lie, I do too.

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