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9 Times Dean Winchester Was The Biggest Hypocrite On Supernatural

For 15 years, Sam and Dean Winchester — played masterfully by Jared Padalecki and Jensen Ackles, respectively — saved people, hunted things, and fought the good fight on "Supernatural." They killed demons, banished ghosts, and iced the Devil himself, with each next threat even bigger than the last. By the time the show ended, the Winchesters had made their way through a half-dozen core cast members, multiple showrunners, and countless classic rock tunes.

Between the two brothers, Dean Winchester, the eldest of the two, has always been the macho hero who usually gets to be the one to take out the season's most recent big bad — and also Hitler. Yeah, Dean killed Hitler, and he won't let us forget it. But beyond his manly exterior and rugged good looks, Dean is probably the show's biggest hypocrite. That's right: There are countless "firm" stances Dean took early on in the series — and even later, by the show's end — that he quickly contradicted. Sure, we're all hypocrites in some ways, but Dean is arguably one of the most self-righteous hypocrites you'll ever see on television who somehow remains likable. Sam can be one too, but Dean's sins — especially given that they often go unnoticed or uncorrected — are arguably a bit more egregious. 

While there are plenty of examples we could put on this list, we decided it best to limit ourselves to the 9 times that Dean was the biggest hypocrite on "Supernatural."  

1. The constant resurrections

Probably the biggest one on the list is Dean's constant desire to resurrect Sam. Yes, this goes for other characters too — he once tried to convince Death to resurrect their half-brother Adam, though he didn't try that hard — but he mostly just cares about his younger brother Sam. Sam means the world to Dean, especially since he practically raised his brother, and although he was the only directly responsible for pulling Sam back into a life of hunting, Dean ultimately wanted him to have a normal life (another hypocritical Dean moment, but we digress).

After chastising people earlier this season — and throughout the rest of the series — for making a deal with a Crossroads Demon, Dean makes one himself after Sam is murdered by one of the Yellow-Eyed Demon's other Special Children. This deal ends up sending Dean to Hell for 40 years in Hell-time (4 months topside) and has some pretty massive ramifications. But Dean learned from his mistakes, right? Wrong.

After Sam threw himself — and the Devil — into the Lucifer's Cage, Dean tried everything to get Sam out to no avail. Years later, in the Season 11 episode "Red Meat," Dean overdoses on drugs in order to talk to a Reaper who might bring Sam back to life after he thought his brother was dead. Thankfully, Sam wasn't actually dead, but Dean's ability to learn seemed to be. Thankfully, he ended up six feet under before Sam did, so no more resurrections.

2. Not forgiving Sam for freeing Lucifer

Sam and Dean have gone through their fair share of disagreements over the years, most of them pretty minor. One of the biggest was Dean's refusal to forgive Sam after he let Lucifer out of the Cage. Sure, Sam's demon-blood binge was not a good look and his Season 5 redemption arc was absolutely necessary given his descent into darkness the previous season, but Dean had no right to hold that against him given his own past mistakes.

For starters, Sam didn't know that killing Lilith would result in the release of the Devil from his prison in Hell, meaning his intentions weren't for evil, but rather for good. Besides that, Dean was put in a very similar situation during his own Hell tour, when he was the first "righteous man" to turn and torture a soul in Hell, thus kickstarting the Apocalypse. Yes, Sam freed Satan to wreak havoc upon the world, but Dean was the entire reason the Apocalypse happened in the first place, and Sam didn't even think to put that guilt upon him.

The Apocalypse arc from Seasons 4 and 5 is "Supernatural" at its absolute best, bringing series creator Eric Kripke's original vision for "Supernatural" to a close.  Sadly, that doesn't mean that Dean was at his best. For a guy who did some pretty unspeakable and shady things to people in Hell, he doesn't really have the right to condemn Sam for doing the same.

3. Walking out on his family

After capturing the Devil and sealing Sam's fate with him in Hell, Dean fulfills his promise to Sam and meets up with his true love Lisa Braeden and her son (and possibly his son, too) Ben in order to start a brand-new "apple pie" life. Although Dean spent much of that year hoping to break Sam out of his fiery prison, he successfully builds a "new normal" with his makeshift family. Dean and Lisa love one another, and Dean becomes a father figure to Ben, who fights to keep Dean in his life even after Dean re-joins a resurrected Sam on the road.

By the time Season 6 ends, Crowley's lackeys kidnap Lisa and Ben, which results in Lisa's own near-death experience. Forever the hero, Dean busts in to exorcise the demon and save his family before convincing the angel Castiel to heal Lisa's wound. But, fearing for their safety, Dean does one of the most hypocritical things he's ever done — he has Castiel erase their memories of him. Not only does Dean make them forget him, but he genuinely believes that they're better off.

For a guy who always talks about the importance of family, Dean takes the "easy" road out when it comes to his own, skipping town the moment things get "too dangerous" for Ben and Lisa. Of course, this isn't the first time he runs out on family, as he left his half-brother Adam in Hell earlier that season.

4. Killing Sam's monster friend

In Season 7's "The Girl Next Door," Dean is introduced to Amy Pond, a monster friend of Sam's whom he met and helped when they were kids. Amy is a kitsune who has a young son; because of his monster condition, he needs human brains in order to live. Amy isn't the killing kind, but with her sick son's life at stake, she had no other choice — though it's worth noting that she never killed a wholly innocent person, only drug dealers and violent criminals.

Although Sam does everything he can to let Amy and her son Jacob go free, Dean catches up to him. Sam tries to convince Dean that Amy is harmless, but Dean sticks to his "monster killing code" and tracks her down, killing her right in front of her son. A few episodes later, Sam finds out, which causes strife between the brothers. Besides the fact that Dean has let monsters go in the past, the thing that makes this especially bad is that Dean becomes best friends with a vampire named Benny the following season.

When explaining it to Sam, Dean describes Benny as a brother and someone who will stick by him no matter what. While this proves to be true, Benny is also a blood-sucking murderer, which Dean seems to conveniently forget about. Eventually, the Winchesters even ally themselves with select witches and werewolves.

5. Letting his daughter die

Whether Ben Braeden is Dean's biological son or not remains unclear, but Dean did at least have one child over the course of the 15 seasons of "Supernatural." If you forgot about Emma after all this time, don't beat yourself up too badly; Dean clearly forgot about her too. An Amazon by birth, Emma was conceived magically during the Season 7 episode "The Slice Girls" after a one-night stand that Dean had with her mother Lydia — who's still at large, by the way — and is killed by her uncle Sam after she attempts to kill her father.

Though Emma's death is very directly Sam's fault — he's the one who pulled the trigger — Dean doesn't so much as lift a finger in protest. Though Dean seems visibly saddened by Emma's death, he gets over it pretty quickly, pushing it down with all the other trauma he's been through. Again, given Dean's constant protests about family throughout the show, it seems odd that he doesn't try to fight any harder for his own flesh-and-blood daughter. Sure, she's a monster, but she's his monster.

Beyond that, Dean doesn't even confront Sam about it, which is sort of odd given their often explosive history. It's possible that Dean felt a bit guilty after killing Sam's friend Amy earlier that season. Interestingly enough, Emma never killed anyone before Sam executed her, which maybe makes Sam a bigger hypocrite here than Dean. 

6. Working with demons (and monsters)

When Sam betrays Dean for the demon Ruby early on in the series, Dean is understandably furious. In fact, the whole trusting or working with demons bit becomes a huge no-go for Sam and Dean throughout the next few seasons, especially after trusting Ruby led to Lucifer's freedom. So it comes as a huge surprise when the Winchesters begin trusting — or at least working alongside — demons like Meg and Crowley. Dean travels to Chicago with Crowley as early as Season 5 to make a deal with Death in order to stop the Apocalypse and Sam barely bats an eye.

By the time Dean becomes a demon in Season 10, he and the King of Hell Crowley are uneasy pals, traveling around making demon deals and causing chaos together. Yes, Dean is a demon at this point, corrupted by the Mark of Cain, but given how neutral some demons can be, including Cain himself, his time with black eyes seems to reveal something about his character. No doubt, Dean never fully trusts a demon — and how could you? — but he's worked with plenty along the way. 

Given his anger with Sam for choosing Ruby over him years ago, it's interesting that Dean then decides to ally himself with the likes of Benny the vampire in Season 8, a character who becomes a close friend and another brother to Dean during their time in Purgatory. Seems pretty sketchy to us. 

7. The saving people mantra

From the series' second episode "Wendigo," Dean has reminded Sam that "saving people [and] hunting things" is their official "family business." This iconic line is a staple of "Supernatural," often repeated and parodied throughout the 15-season series. What's worth noting about Dean's quote is that he puts saving people first, before hunting things. Ironic, given that after a few seasons of battling demons and ghosts, the Winchesters seem to care less and less about saving the folks possessed by these entities — well, unless they know them personally.

That's right: though they try to exorcise demons out of folks in the first few seasons, Sam and Dean later slice their way through plenty of demonic hosts to kill the wicked spirits. The same goes for angelic hosts too, as they start to kill them with ease. By the beginning of Season 11, Sam has a change of heart, hoping to save as many victims of possession as they can. Dean, on the other hand, doesn't make any extra efforts, and only saves those whom he already cares deeply about.

For a guy whose entire life revolves around saving lives — and make no mistake, the Winchesters have saved countless lives along the way — Dean's disregard for those possessed by angels and demons is a major character flaw. Sure, he wants to kill his enemies, but at the cost of how many innocents? No wonder he meets his own bloody end. 

8. Giving up the fight

One thing that's always been clear about Dean Winchester is that he never gives up. Regardless of the odds they're up against, Dean will fight to the death if it means he's gonna go down swinging. It's this bravado that led him to confront the Devil head-on, send Dick Roman to his doom, and ultimately attempt to kill Death and trap the Darkness. But, after being tricked by an alternate-universe version of the archangel Michael, Dean was unable to expel the angel from his mind and was instead forced to trap him within.

Unfortunately for Dean, the mental anguish was more than he could bear. In response, he built a Malak Box designed to trap him (and the archangel) inside for eternity. With this act, Dean tells Sam that he's basically given up on the fight; that it's easier for him to just check out rather than beat the angel on his shoulder. Dean's continued pessimism becomes irritating for Sam, and eventually the younger Winchester clocks his older brother to get it through his head that he's not allowed to quit.

Although it takes the better part of Season 14, Dean eventually comes around and they do find another way to get rid of Michael — well, that version of him, anyway — for good, destroying the angelic spirit forever. Thankfully, Dean doesn't ever give up on the fight again, even when going up against Chuck/God himself. 

9. Making Sam promise to let him die

Dean doesn't actively give up ever again, but in the series finale, he does finally embrace death after a routine hunt goes south. "Carry On" got plenty of mixed reviews, but Dean's final moments with Sam are some of the most-praised aspects of the episode. Admittedly, Dean's final wish that Sam won't bring him back again may just be some well-earned character growth after all these years, but given his track record — and the fact that there's no way Dean wouldn't've saved Sam were their roles reversed — this moment felt pretty hypocritical to some.

There's no denying that Sam and Dean made the right choice here, though. Letting Dean stay dead meant that Dean was finally out of the hunting life and that Sam had the chance to live his own full and normal life, just as he always wanted. Thankfully for Dean, time works differently in Heaven, and soon enough he and his brother are reunited in the afterlife. Of course, had the roles been swapped, the finale would've played out very differently, but that's probably why Dean was the one who had to go in a final blaze of glory.

Regardless of his own flaws, there's no doubt Dean Winchester is a hero. He may not see himself that way, but he's helped save the world more times than just about anyone. Of any hero in the world of "Supernatural," he deserves to finally be at peace.