Summary
- The Winchesters' high moral code and heroics in saving humanity are overshadowed by their villainous decisions, such as Sam trusting Ruby and releasing Lucifer.
- Dean's decision to kill Death to save Sam leads to disastrous consequences, unleashing The Darkness onto the world.
- Despite preaching the importance of family, the Winchesters cruelly forget about their half-brother Adam and ignore his plight, tarnishing their reputation as morally upstanding individuals.
While the Winchesters saved the world countless times over the course of Supernatural, and maintained a mostly high moral code, the brothers weren't completely free of sin, and in fact, many of their decisions make them just as villainous as the demons they fight. Supernatural is a paranormal mystery series that spanned for 15 seasons on the CW. It follows Sam and Dean Winchester, two brothers who dedicate their lives to hunting monsters and protecting humanity from the universe's many forces of evil.
For the most part, Sam and Dean proved themselves to be heroes during Supernatural, often putting their lives on the line to save humanity as a whole. However, sometimes the Winchesters' morals, belief systems, and personalities led them astray, and were the reason why they made completely awful choices. In particular, Dean's tight grip on Sam and Sam's constant streak of independence are two problems with which the brothers often made their worst decisions. More than that though, some of the Winchesters' poorest moments were done senselessly and over a long period of time.
10 Sam Trusted Ruby & Released The Devil
One of Sam's most significant mistakes is trusting Supernatural's Ruby character and releasing Lucifer. After Dean's death in Supernatural season 3, Sam begins harnessing his psychic powers by drinking demon blood. While Ruby's persuasion affects Sam some, he does knowingly allow himself to be a part of Ruby's plan. Worse than that, Sam has a sexual relationship with Ruby, further confusing his sense of right and wrong. Above all, by working with Ruby, Sam becomes strong enough to kill Lilith which, unbeknownst to him, is exactly what needs to happen to release Lucifer from his cage. In this way, Sam's poor choices made him a villain.
9 Dean Killed Supernatural's Death To Protect Sam
While Dean's decision to kill Death to save Sam's life seems like a worthy cause, the consequences of his actions are actually much more ruinous. During Supernatural's season 10 finale, Dean calls on Death to kill him because of the Mark of Cain's horrible effects. Death explains that he can't kill Dean because the Mark keeps the Darkness locked away, but can bring him to a safe space if he kills Sam first. In response, Dean kills Death and allows the Mark of Cain to be removed, releasing The Darkness onto the world. This decision opens an entirely new and world-ending can of worms in the form of Amara.
8 The Winchesters Forget About Adam
For characters that talk so often about the importance of family, the Winchesters seem fairly cruel for forgetting about their half-brother Adam. In Supernatural season 4, it is revealed the Adam is the vessel of the angel Michael and Sam is destined to be Lucifer's. When they both end up locked in the Cage, Dean can only save one brother and he chooses Sam. While this makes a sort of sense, the main issue is that Sam and Dean never really try to save Adam ever again. Assuming he's a lost cause, they completely ignore the third Winchester brother. This is a particularly rough look for the morally upstanding Winchesters.
7 Sam Didn't Look For Dean In Purgatory (Or Kevin In Hell)
Supernatural season 8 sees many questionable decisions and the first of these is when Sam doesn't look for Dean in Purgatory or Kevin in Hell. After Dean and Cas are sent to Purgatory and Kevin is kidnapped by Crowley at the end of season 7, Sam makes an assumption that they are both lost to him, and tries to move on with his life. Considering how often Dean has survived alternate dimensions, and the innocence of Kevin as a mere human, it's incredibly selfish that Sam would choose to start a new life rather than making an attempt to find his brother and friend. This choice emphasizes Sam's carelessness.
6 Dean Kicked Cas Out Of The Bunker
A major Supernatural season 9 mishap is when Dean forces Cas to leave the Bunker. While Dean is, in his way, trying to protect Cas from Gadreel, this decision is absolutely heartbreaking for Cas. In his human form, Cas needs Dean now more than ever, and Dean ignores that for the mess he himself created. After everything Cas has done for Dean over the seasons, the decision to kick him out without help is a completely cruel one that proves Dean's selfishness. Plus, it shows how harmful it is when Dean refuses to be honest when it is most necessary.
5 Sam Killed A Nurse For Demon Blood
Though some may argue that this Sam moment was highly influenced by his demon blood addiction, it is still a choice that Sam had the chance to not make, and that he did anyway. During Supernatural season 4, Ruby presents Sam with one of Lilith's demon minions, but before Sam can kill her, Ruby convinces him that he should drink her blood to increase his powers. Trying to save itself, the demon allows the nurse it is possessing to spring forth, begging for her life.
In a devastating scene, Sam drags the demon to his car, despite her pleas. She talks about her husband and her job, but Sam coldly throws her into the trunk. Preparing to kill the demon, Sam hesitates for a moment, but he ultimately kills the demon and nurse and drinks her blood for his own gain. While Sam has Ruby ing this decision and a tampered voicemail from Dean pushing him on, he arguably still had enough free will at this moment to be swayed by the nurse, yet he killed her anyway. This is certainly one of Sam's lowest moments.
4 Dean Tricked Sam Into Accepting Gadreel
One of Dean's biggest betrayals is when he tricks Sam into letting Gadreel possess him. At the start of Supernatural season 9, Sam is dying and Dean prays for an angel to help him. Gadreel comes forward and convinces Dean that if he possesses Sam, he can heal him. Dean allows Gadreel to persuade Sam to say yes, despite Sam's strong reservations. Although Dean is trying to save Sam's life, this decision is an awful one because it overrides Sam's opinions and ability to consent. Plus, making Gadreel Supernatural's main character leads to Kevin's death and other terrible events that Dean could have prevented if he let fate win.
3 The Winchesters Trap Jack In A Ma'lak Box
A somewhat contentious choice the Winchesters made in Supernatural season 14 is when they trapped Jack in a Ma'lak box. After Jack accidentally kills Mary Winchester due to his soullessness, Sam and Dean decide to put him into a warded box, so he can't hurt anyone else. Despite promising that they'll let him out soon, the brothers have no intention of doing that. Fueled by their bitterness at their mother's death, the brothers make Jack suffer, despite the fact that him losing his soul was for them and their battles. This evil move ultimately backfires on them too when Jack breaks out, angry with how they manipulated him.
2 Dean Killed Amy The Kitsune In Front Of Her Son
The cruelest thing that Dean Winchester ever did in Supernatural was killing Amy the Kitsune. As one of Sam's childhood friends, Amy is a nice character that seems determined to fight against her kitsune instincts. In fact, the Winchesters seem ready to leave her, convinced she can handle her situation, however Dean actually stays behind without Sam's knowledge and kills Amy. Worse than that, he does it in front of her son. This scene is terrible because it is a breach of Sam's trust, a lack of faith in Amy, and a traumatic moment that he caused for a little boy. This is by far Dean's most villainous moment.
1 The Winchesters Take Advantage Of Their Friends
The Winchesters' biggest mistake throughout Supernatural is the way they take advantage of their friends and peers. As shown in the Supernatural episode, "Weekend at Bobby's," the brothers often have no clue what their friends are going through and yet continue to barrage them with questions and pleas for help. Worse than that, these ing characters almost all get killed by working with the brothers. In this way, the Winchesters use their friends for their skills, i.e. Bobby, Kevin, Charlie, etc, then inevitably lose them through poor protection and high risk. In the end, this is what makes the Winchesters worse people than they first seem in Supernatural.
