As Supernatural gets closer and closer to its end, its beloved fans want to squeeze all the enjoyment they can out of it. After all, at fifteen years old this show is older than some of its core demographic now (teen-young adult). For many fans, the show has been a staple of their lives for a very long time. They have fallen in love with the Winchester family and loved it like it was their own.
However, the Winchesters are far from perfect. Arguably, the reason fans like them so much is because they aren't. All of the family has been involved in some serious destruction.
But, at the end of the day, how horrible could their actions be if they are the heroes? Just wait and see.
10 John Winchester - Family Last, Hunting First
There's a lot of "Bad Dad John" jokes in the fandom, and maybe this is the easy answer, but it's an honest one. John Winchester constantly chose hunting over his children, which is ironic when he condemned his wife's parents for doing the same thing. Worse, he also ruined other families by choosing the hunt. He willingly left his friend Bill to perish during a hunt, even though he had a wife and daughter.
Losing Mary clearly changed John. It broke something in him and turned him into a selfish hunter with a one-track mind. His sons deserved better. He may have loved them, but he never made them his first priority and always judged them for choosing any path except vengeance through hunting.
9 Emma Winchester - Tried to Sacrifice Her Father
Amazons are an interesting species, but The Winchesters didn't know how interesting until Dean got one pregnant. His fling then gave birth and within days the child was a full-grown teenager named Emma. However, to become a true Amazon, she had to sacrifice her father. Them's the rules.
Understandably, Dean wasn't too keen on that.
Even though Emma was days old and born into a slightly violent culture, trying to knock-out one of the beloved Winchester Bros. was a big no. If it wasn't for Sam being extremely cold-hearted, Dean might have lost his life to help Emma get what she wanted. In her short life, it was the worst thing she did (and it was still pretty bad).
8 Mary Winchester - Making A Deal With Azazel
Mary Winchester grew up in a family of hunters, tracking down the supernatural creatures of the world and stopping them from hurting innocent mortals. Her entire life she knew the dangers of vampires, werewolves, angels, and especially demons.
However, experienced as she was, young Mary still made a deal with Azazel to resurrect John. Now, some people might say there are worse things she did, but this one deal gave him the ability to break into her home and burn her alive a few years later. And that kicked off John's selfish crusade of vengeance, which also messed up her kids and cursed them with the hunter's life.
It's the worst thing she did for her sons, even if they wouldn't exist without the deal.
7 Henry Winchester - Stealing The Impala
Okay, most Winchesters have a laundry list of terrible things that could be picked. However, there is one guy who is much more wholesome than the rest of his family: Henry Winchester. Father of John Winchester, Henry went forward in time to try to help his son and the future. When John wasn't there, he helped his grandsons.
Other than being a helpful guy, he sacrificed himself for the greater good. So, the only bad thing he did was freaking out when he appeared and trying to steal the infamous Impala.
Now, mind you, that Impala in legendary in the Supernatural fandom so it's still a pretty big deal. It's just compared to everyone else, Henry's "worst thing" was pretty tame.
6 Sam Winchester - Demon Relations
There are so many things Sam has done wrong, from shooting his niece, getting possessed, being a vessel of evil, the works. But arguably the worst thing he's done is consort with demons, despite all the things he knows about them. And no, not just his dumb deals he's made (though he's made many and they count here). He's also had relationships with them. Looking at you, Ruby.
While some redemption arguments can be made for demons, they literally destroyed his mom, dad, and girlfriend. Why would Sam even dare get involved with any of them, romantic or otherwise?
Not only is this his worst transgression, but it's also his dumbest. Sam should definitely know better; none of them have ended well.
5 Adam Milligan - Betrays His Half-Brothers
The Winchesters tend to have family popping up out of nowhere (quite literally, in the case of time-travelling Henry). But no one had quite the impact as Adam Milligan. A boy that John Winchester abandoned, Adam later reconnected with his siblings. However, they didn't exactly get off to a great start. After all, the other two were renowned hunters of the supernatural and Adam was just, well, Adam.
Fans can't really blame him for getting tricked by a demon into betraying his brothers. That doesn't make it any less horrible, though, especially since it ended in him and Sam in Hell.
The really cruel part, though, is that they left Adam in Hell to rot. Poor, misguided guy.
4 Jack Kline - Killed Mary
It's very on brand for the Winchester brothers to adopt the Anti-Christ, isn't it?
After foiling Lucifer's plans to use Jack to bring about the end of days, Sam and Dean adopt him as an honorary Winchester. Unfortunately, that doesn't go completely well for the family. After an incident where Jack's morality is taken away, he wipes out the ressurected Mary Winchester just for annoying him.
Jack does have a lot of Devil-shaped hurdles to overcome, but that's a pretty awful thing to do to your foster-dads.
3 Cain - Killed His Brother
Of course, because this is Supernatural, Sam and Dean are the descendants of Cain and Abel. The show flips the story on its head, though. Instead of Cain being a jealous and evil brother, he just wants to save Abel's soul. Abel was talking with the Devil and letting the guy corrupt him mind. God told Cain that the only way to save Abel was to send him to heaven. Directly and immediately.
A good Christian man, Cain obliged and ended his own brother's life. Even with noble intentions, Cain never gave Abel the chance to save himself and stopped his life short. That's a sin that good intentions cannot absolve. And, ultimately, it turned him into one terrible demon.
2 Abel - Consorted With The Devil
Despite all the stories told in the Bible, according Supernatural, Abel was listening to the Devil's whispers in his ears. He was letting the demon infect him and turn him from a good son into a dark vessel. Though it was Cain who ended Abel's life, the younger brother still made the mistake of getting involved with the Devil.
Because Abel listened, he condemned his brother to demonhood and Hell. Then, they began the cycle of their descendants being the vessels for Michael and Lucifer. His flirtation with darkness cursed their entire bloodline.
1 Dean Winchester - Lying To Sam (All The Time)
There are a lot of one-off bad things that Dean has done, involving a lot of stabbing, destruction, possession, and the like. However, overall his greatest flaw and vice is his lying problem. Worse, it's often lying by omission. Dean tends to learn important things and then thinks it's his job to gate-keep it from his loved ones. Even in cases where knowing things could help them make better choices and save lives.
He kept his father's last words from Sam, he hid his experiences in hell, he keeps a giant bundle of secrets under him just because he doesn't feel like sharing these important, need-to-share information.
Since the entire show is about their hunter work as a team, that is a recipe for the worst teammate ever. Seriously.