Unveiling the Dark Secrets: 10 Mind-Blowing Supernatural Moments That Will Change Your Perspective on Sam & Dean

Summary

Despite the Winchesters' commitment to a noble moral code and their valiant efforts to protect humanity, their heroic deeds are often overshadowed by the detrimental choices they make. One such example is Sam's misplaced trust in Ruby, which ultimately resulted in the release of Lucifer.

Furthermore, Dean's fateful decision to kill Death in order to save his brother, Sam, had catastrophic consequences as it inadvertently unleashed The Darkness upon the entire world.

Despite preaching about the importance of family, the Winchesters callously overlook their half-brother Adam and dismiss his struggles, tarnishing their reputation as morally upright individuals.

Throughout the 15-season run of Supernatural, while the Winchesters consistently save the world and adhere to a mostly high moral code, their actions reveal a darker side that aligns them with the very villains they battle. Supernatural, a paranormal mystery series, centers around Sam and Dean Winchester, two brothers committed to hunting monsters and safeguarding humanity from the countless malevolent forces of the universe.

For the most part, Sam and Dean showcased their heroism throughout the series Supernatural, frequently risking their lives to safeguard humanity as a whole. Nevertheless, there were instances when the Winchesters' moral compasses, belief systems, and individual personalities led them down the wrong path, resulting in incredibly poor decisions. In particular, Dean's firm control over Sam and Sam's unwavering streak of independence posed as two major obstacles for the brothers, often influencing their worst choices. Moreover, some of the Winchesters' lowest moments were not only senseless but also spanned an extended period of time.

10 Sam Trusted Ruby & Released The Devil

One of Sam's most significant mistakes is putting his trust in Supernatural's Ruby character and ultimately freeing Lucifer. Following Dean's demise in Supernatural season 3, Sam begins tapping into his psychic abilities by consuming demon blood. While Ruby's persuasion does influence Sam to some extent, he makes a conscious decision to participate in Ruby's scheme. Adding to his confusion between right and wrong, Sam engages in a sexual relationship with Ruby. Most notably, by aligning himself with Ruby, Sam acquires the strength necessary to eliminate Lilith, unknowingly fulfilling the requirements for releasing Lucifer from his confinement. Consequently, Sam's regrettable choices lead to his transformation into a villain.

9 Dean Killed Supernatural's Death To Protect Sam

While Dean's decision to eliminate Death in order to protect Sam's life may appear noble, its ramifications are in fact far more disastrous. In the gripping climax of Supernatural's tenth season, Dean implores Death to end his life due to the gruesome consequences of the Mark of Cain. Death, however, reveals that he is unable to kill Dean as the Mark acts as a barrier against the Darkness. Instead, he proposes that Dean can be transported to a secure location if he first kills Sam. In a shocking turn of events, Dean opts to slay Death, ultimately leading to the removal of the Mark of Cain and the subsequent release of the malevolent entity known as The Darkness. This fateful choice not only ushers in a whole new era, but also brings about the potential end of the world in the form of Amara.

8 The Winchesters Forget About Adam

Despite frequently emphasizing the significance of family, the Winchesters display a rather callous disregard for their half-brother Adam. In Supernatural season 4, it is revealed that Adam serves as the vessel for the angel Michael, whereas Sam is destined to embody Lucifer. Subsequently, when both brothers become trapped in the Cage, Dean faces the impossible choice of rescuing only one sibling, ultimately opting for Sam. While this decision holds a certain logic, the crux of the matter lies in the fact that Sam and Dean make no further attempts to save Adam afterwards. Dismissing him as a lost cause, they effectively neglect their third Winchester brother. This lapse in care casts a harsh shadow over the morally righteous Winchesters.

7 Sam Didn't Look For Dean In Purgatory (Or Kevin In Hell)

Supernatural season 8 witnesses a series of questionable decisions, with the first being Sam's neglect to search for Dean in Purgatory or Kevin in Hell. Despite Dean's history of surviving in alternate dimensions and Kevin's vulnerable state as a mere human, Sam selfishly decides to forge ahead with his own life, assuming that his brother and friend are lost to him. This choice highlights Sam's disregard for their well-being and underscores his careless nature.

6 Dean Kicked Cas Out Of The Bunker

One major mishap in Supernatural season 9 occurs when Dean compels Cas to vacate the Bunker. While Dean may believe he is safeguarding Cas from Gadreel, this choice deeply devastates Cas. In his human form, Cas requires Dean's support more than ever, yet Dean disregards this, despite being responsible for the predicament. Considering everything Cas has sacrificed for Dean throughout the seasons, this heartless decision to expel him without assistance reveals Dean's selfishness. Moreover, it exemplifies the detrimental consequences of Dean's refusal to be honest when it is most crucial.

5 Sam Killed A Nurse For Demon Blood

Although some may argue that Sam's actions in this Sam moment were heavily influenced by his addiction to demon blood, it is important to acknowledge that he had the opportunity to choose differently, yet he ultimately made the decision to proceed. In Supernatural season 4, Ruby presents Sam with one of Lilith's demon minions, with the intention of him killing her. However, Ruby convinces Sam that he should consume the demon's blood in order to enhance his powers. Upon realizing that the demon is desperately pleading for her life, Sam callously disregards her pleas and forcefully places her in the trunk of his car. Despite the demon attempting to appeal to his emotions by discussing her personal life, Sam shows no mercy and proceeds to kill the demon and the nurse she possessed, consuming her blood for personal gain. While Sam had support from Ruby and a manipulated voicemail from Dean, it can still be argued that he had enough agency at this moment to be influenced by the nurse's desperate pleas; nevertheless, he cruelly ends her life. Undoubtedly, this stands as one of Sam's most morally reprehensible moments.

4 Dean Tricked Sam Into Accepting Gadreel

3 The Winchesters Trap Jack In A Ma'lak Box

One of the most devastating betrayals Dean commits is his deceptive act of convincing Sam to allow Gadreel to possess him. In the beginning of Supernatural season 9, Sam finds himself on the verge of death, prompting Dean to desperately seek assistance from an angel. In response to Dean's prayer, Gadreel steps forward, successfully persuading Dean that by taking possession of Sam, he can heal him. Despite Sam's strong reservations, Dean allows Gadreel to influence him into coaxing Sam to consent. However, this decision proves to be immensely destructive as it not only disregards Sam's opinions and ability to give consent, but also leads to the demise of Kevin and a series of other horrifying events that Dean could have prevented by simply trusting in fate.

An incredibly controversial decision was made by the Winchesters in Supernatural season 14 when they opted to imprison Jack in a Ma'lak box. Tragically, Mary Winchester met her demise as a result of Jack's soullessness, prompting Sam and Dean to confine him within a specially protected container, preventing him from causing harm to others. Despite initially assuring Jack that he would be released soon, the brothers secretly harbored no intentions of fulfilling this promise. Driven by their grief over their mother's untimely death, they opted to subject Jack to suffering, even though his loss of soul was intended to benefit them and their battles. However, this wicked scheme ultimately boomeranged when Jack successfully broke free, seething with rage over the way they had manipulated him.

2 Dean Killed Amy The Kitsune In Front Of Her Son

1 The Winchesters Take Advantage Of Their Friends

The cruelest act committed by Dean Winchester in the Supernatural series was the killing of Amy the Kitsune. Amy, who was one of Sam's close childhood friends, portrayed a kind-hearted character determined to resist her inherent kitsune nature. Surprisingly, the Winchester brothers initially believed that Amy possessed the strength to handle her situation and were prepared to depart, trusting in her abilities. However, in secret, Dean chose to remain behind, unbeknownst to Sam, and mercilessly ended Amy's life. The horrifying aspect of this scene lies in the betrayal of Sam's trust, Dean's lack of faith in Amy, and the resulting trauma inflicted on her young son who witnessed the ghastly act unfold. Without a doubt, this particular moment stands as Dean's most sinister and villainous.

Throughout Supernatural, The Winchesters' treatment of their friends and peers reveals their biggest mistake. In the episode "Weekend at Bobby's," it becomes evident that the brothers are often oblivious to the struggles their friends are facing, yet they persistently burden them with questions and pleas for assistance. To make matters worse, the majority of these supporting characters meet a tragic end while working alongside the brothers. In effect, the Winchesters exploit their friends' abilities, such as Bobby, Kevin, Charlie, and others, only to ultimately fail in protecting them and subjecting them to immense danger. In the end, it is this pattern of behavior that proves the Winchesters to be far less honorable than initially perceived in Supernatural.