Dean Winchester is the toughest guy around, but anyone who watches Supernatural knows that he still has a soft side that is not often explored on the show. While Dean constantly shows off his hard side, that also tends to be when he messes things up and makes dumb mistakes. Don’t get us wrong, we love Dean and he’s easily our favorite Winchester, but he can be a total idiot. Whether he is risking his life (for the billionth time) to save Sammy or he’s not telling Sam something to “protect him,” Dean can f*ck stuff up. Big time. We will always love the guy, but when he does really dumb stuff, he can make it hard for us to always support his choices.
16. The time that he went and sold his soul
Season 2, Episode 22 – “All Hell Breaks Loose – Part 2”
You would think after having his dad sell his soul to save him, Dean wouldn’t turn around and waste that second shot at life. Not saying that saving Sammy is wasting his life, but you get what we mean. This was still very early on in the series and it was long before we (and Dean) realized that Sam and Dean just will not stay dead. So, in the realm of dumb things that he’s done, finding a demon to sell his soul to for a one-year contract, instead of the standard ten-year contract, is not the MOST moronic thing. But it was still dumb. The move eventually got Dean killed and sent to hell. But then we got to meet Castiel when he raised Dean from perdition, so things worked out.
15. The time Dean let Gadreel into Sam’s body without Sam knowing it
Season 9, Episode 1 – “I Think I’m Gonna Like It Here”
This one is seriously not cool. Even though he is literally the only family that Sammy has (well at least, at that time), that doesn’t mean he should make big enormous decisions for his brother. Especially when his brother expressly told him that he does not want to be saved if it means Dean has to do something crazy. But by season nine, we know that Dean and Sam will tell each other “don’t save me” and then go and save each other anyway. What made this awful was that Gadreel was pretending to be a good angel, Ezekiel, and when Dean asked Castiel if they could trust Ezekiel, Cass said yes. Could they trust Gadreel? Just ask Kevin that one…
14. Getting close to Ben and Lisa, again
Season 6, Episode 1 – “Exile on Main Street”
For this one, we don’t mean that what Dean did was dumb because this hurt Ben and Lisa (even though it did). It’s more that Dean has always wanted a normal life, even if he’s tried to tell his brother otherwise. Dean remembers a time when things were perfect with his parents and baby Sammy. But ever since Azazel killed his mother, Dean’s life was forever changed. Hunting became his father’s life, thus it became Dean’s too. Dean is an excellent hunter, probably the best there is. But the time he had with Ben and Lisa gave him a taste of a different life. He should have known better than to think he could live a normal life after his brother got locked in Lucifer’s cage.
13. When he took the Mark of Cain
Season 9, Episode 11 – “First Born”
There weren’t many options when it came to fighting Abaddon, seeing as she was a Knight of Hell and virtually impossible to get rid of. In order to kill her, Dean and Crowley learn from Cain that they need the First Blade. But in order to wield the First Blade, someone needs to bear the Mark of Cain. Obviously, Dean doesn’t even consider what the after effects of this might be and immediately accepts to take the mark. As we later learn, the Mark of Cain came with a serious price. But did Dean even think about that? Nope!
12. When he almost dies because he hears his father’s voice
Season 3, Episode 14 – “Long-Distance Call”
John Winchester was a complicated man. When it came to Dean, John probably treated him better than Sam, but it wasn’t like he went around telling his older son that he was proud of him or anything. It was a better relationship than what Sam and John had, but still, it was obvious that Dean yearned to be loved by his father. When Dean gets a phone call from his dad, telling him he can get him out of the deal he made with a demon, Dean immediately believes it to be his dad. Even though John had been dead for a year by then. Dean didn’t listen to Sam, who was very skeptical about the whole thing, and Dean walked right into a trap!
11. When he trusted Crowley over Sam or Castiel and got himself turned into a demon
Season 9, Episode 23 – “Do You Believe in Miracles?”
The relationship between Dean, Crowley, Sam, and Castiel was complicated one. Could they ever really trust Crowley? The short answer: no. Long answer? Maybe. But either way, Dean should never have trusted Crowley over his brother or his best friend. No matter what kind of disagreement Sam and Dean have gotten in (minus the time Sam had no soul), they always meant the best for each other. So, it was pretty jarring for viewers to watch Dean trust Crowley to help him and ignore the warning signs brought up by his brother. And that is how we wound up with Deanmon!
10. The time he intentionally died just to talk to Death
Season 6, Episode 11 – “Appointment in Samarra”
By this point in the series, dying probably was not the scariest thing for Dean. He was certainly more afraid of living without Sam. But Sam wasn’t really Sam, seeing as he didn’t have his soul. Sam without a soul was pretty ruthless. So, Dean went and visited an old friend of his dad’s, and paid Dr. Robert to be killed and then revived. That’s even though Dr. Robert only had a 75% success rate. Dean wanted to die and talk to Death to see if Death could help him get Sam’s soul back, but it was a wildly risky choice, especially considering that Sam didn’t even want his soul back.
9. The time he melded minds with a dog
Season 9, Episode 5 – “Dog Dean Afternoon”
Dean has never been an animal guy, which is fair, it isn’t like he grew up in a normal household where he could have a pet. But seeing as he has no inclination on how to act around dogs, why would he meld minds with one? It was a weird episode to begin with. When Dean and Sam work together, they don’t always think of the risks of using magic. It isn’t like either of them is a witch. Yet, they’re constantly using spells. So, Dean probably should have thought twice before trying this one.
8. When Dean promises Sam he will leave him in Lucifer’s Cage
Season 5, Episode 22 – “Swan Song”
This might seem to contradict what we’ve said so far. Sure, Sam and Dean save each other too often without considering the impact. But to promise not to save your brother? That is just too much. They needed to lock Lucifer in the cage and in order to do so, Sam had to agree to let Lucifer use him as a vessel. But Sam wanted Dean to move on – while Sam was stuck in Lucifer’s cage with Lucifer in hell – and start a new life with Lisa and Ben. And Dean actually did it!
7. Making Sam start hunting again
Season 1, Episode 1 – “Pilot”
Now, hear us out. We’re not trying to upset Supernatural fans. Obviously, we love the Winchester brothers. Supernatural is the best show to hit the CW. The relationship between Dean and Sam cannot be rivaled and has only gotten stronger over the years. Yet, Dean has an insurmountable level of guilt about getting Sam involved in hunting again and how it impacted his brother’s life. Even if it isn’t mentioned every season, it still lingers, some 13 years later. Dean feels horrible for how it “ruined” Sam’s life. If he hadn’t gone to Sam that night, things would be vastly different. But then again, that doesn’t mean that Dean or Sam would be better off, no matter how much Dean might think Sam would have been okay.
6. The time that he killed Death
Season 10, Episode 23 – “Brother’s Keeper”
Have you noticed a theme? When it comes to Sam, Dean will literally do anything to save his brother. He doesn’t care about the consequences. He does not care if it puts himself in harm’s way. He cannot let anything bad happen to Sammy. In order to get rid of the Mark of Cain, Dean appeals to Death to see if the Four Horsemen will help him. At first, Dean wants Death to kill him, but when we learn that the Mark was created to keep the Darkness locked away, it’s pretty clear Death will not let her out. Surprisingly, Death offers to help, but it comes with a price. He will need to relocate Dean far away since Dean can’t give the Mark to anyone else. Although he offered to try it, Dean wound up killing Death instead, naturally.
5. The time he and Sam started the apocalypse by releasing Lucifer
Season 4, Episode 22 – “Lucifer Rising”
So, this one might be more of a dumb thing that Sam did, but Dean and Sam are basically one person and Dean is DEFINITELY partially to blame. Dean has made it his responsibility to take care of Sam and that means watching over him. So, how did he let his brother get involved with Ruby 2.0 and start drinking demon blood again? Like, a lot of demon blood. This negligence led to Sam getting tricked into working with Lilith and ultimately bringing on the apocalypse. Had Dean been paying attention, he might have realized what was going on before the last possible second.
4. When he thought Sam was dead, so he took a bunch of drugs and died too
Season 11, Episode 17 – “Red Meat”
This is some Rome & Juliet shiz. Dean should know by now that his brother isn’t ever actually dead. At least he’s not for long. When it appears that Sam has died after an encounter with werewolves, Dean decides to take a ton of barbituates to die, so he can contact a reaper. That’s even though he killed Death (AKA the boss of all reapers) less than a year before. This was a dumb move because it put another target on Dean’s back from angry reapers and they already weren’t on the best terms. Then Dean died, only to find out that Sam wasn’t actually dead. Thankfully things worked out in the end, but maybe Dean’s first instinct shouldn’t be to die when something happens to Sam.
3. The time that Sam and Dean accidentally released the Darkness
Season 10/11, Episode 23/1 – “Brother’s Keeper” – “Out of the Darkness, Into the Fire”
Again, together, Sam and Dean make some pretty stupid choices. Not just things that impact just them, but things that literally impact the entirety of the world. i.e., setting Lucifer free and starting the apocalypse just so that, years later, they can let the Darkness out of her cage. Don’t forget, the Darkness is 10x worse than Lucifer. To get rid of the Mark, Dean killed Death (as we know), and then he and Sam worked with Crowley, Rowena, and Castiel to use a spell to get rid of the Mark. However, that then led to the release of the Darkness, who was kind of already in love with Dean as soon as she met him. It was the beginning of a very complicated relationship between Dean and the Darkness. His bad choices really just build off of each other!
2. The time Dean managed to get turned into a vampire
Season 6, Episode 5 – “Live Free or Twihard”
Supernatural had vampires before vampires were the ~in~ thing. Vampires on Supernatural aren’t crazy sexy and they don’t pretend to be high school students, contrary to the pop culture norm. Typically, Dean is able to take a vampire out with no problem. Yet this time, he manages to get overpowered by a vampire and then force-fed his blood – to transform Dean into a vampire, too. It doesn’t help that Sam is soulless at this point and even hesitates to kill the vampire who attacked Dean. But because Dean is luckier than he deserves, there is apparently a cure for vampirism which he can take. It’s always something in Supernatural.
1. When he slept with an Amazon and had a baby
Season 7, Episode 13 – “The Slice Girls”
The fact that Dean hasn’t had more pregnancy scares after all of the one-night stands he’s had on the show is pretty incredible. But, still, Dean should not be so sloppy that he doesn’t even realize that he didn’t use protection. He should also always be hyper-aware of the women that he sleeps with. It has happened on more than one occasion that people have used his love of beer and woman against him. Since Dean was careless, of course, the woman that he impregnated is an Amazon that basically trapped him so she could use him to procreate and have a child in under 36 hours. And as if that isn’t crazy enough, Dean was then forced to kill his own daughter. But he couldn’t do it, so Sam saved him and killed Emma.