Unforgivable Blunders: Sam & Dean Winchester's Most Epic Supernatural Fails

Sam and Dean Winchester from Supernatural faced numerous challenges throughout the 15 seasons, often making questionable decisions along the way. While some of their actions were driven by the greater good, like Dean consuming phoenix ashes to eliminate Eve or Sam rallying hunters against the British Men of Letters, who were wiping out American hunters, their unwavering determination to cheat death for each other often resulted in significant consequences for the storyline.

Had Sam and Dean not remained steadfast in their commitment to "saving people, hunting things," they would not have made certain choices, driven by either selfish motives, such as Dean resurrecting Sam to avoid being alone, or without considering the consequences, like tricking Jack into confining himself in a Ma'lak Box. Although their intentions were often justified in their own minds, Sam and Dean have made numerous mistakes throughout Supernatural, leading to ripple effects in their journey.

10 Dean Hunted Even After He Started A “Normal Life”

9 Sam Trusted Ruby The Demon

After Sam descended into hell at the conclusion of season 5, Dean found solace in reconnecting with his previous romantic interest, Lisa, and her son, Ben, striving for a semblance of normalcy and bidding farewell to a life of hunting. During this period, Dean even retired his cherished Impala. Despite grappling with grief and the lingering paranoia ingrained by his past as a monster-hunter, Dean experienced a measure of happiness in forming a family. However, with Sam's unexpected return, Dean gradually succumbed to the allure of hunting once more. Consequently, one of his deepest fears materialized as Lisa and Ben found themselves in imminent danger at the hands of Crowley's demons. Tragically, Lisa was possessed and mercilessly stabbed, almost proving fatal. Had it not been for Castiel's intervention, her life would have been tragically extinguished—arguably, due to Dean's inability to fully distance himself from the hazardous world of hunting as he had initially intended.

Trusting Ruby, despite knowing she was a demon, proved to be one of Sam's most problematic decisions. While he openly acknowledged his reservations about her, he continued to follow her lead. Interestingly, Sam and Ruby never forged a friendship; instead, their volatile relationship gradually contributed to Sam's addiction to demon blood. This internal struggle was a source of both conflict and shame for him, as he chose not to disclose it to Dean, along with other secrets.

To compound the situation further, in season 4, episode 21, Sam intervened and prevented Dean from eliminating Ruby. If Dean had taken the decisive step to end her life, Sam wouldn't have unintentionally released Lilith. Consequently, this chain of events would have averted Lucifer's escape from hell. The preservation of the seals in their original state would have prevented the catastrophic destruction and chaos that unfolded once Lucifer ascended to Earth. One notable instance illustrating this is the devastating impact caused by the Four Horsemen and the countless innocent lives lost as a result of their obedience to the resurrected Lucifer's commands.

8 Dean Started The Apocalypse

In a similar vein to Sam's fatal trust in Ruby, Dean's choice to revive Sam at the conclusion of season 2 initiated the path towards the catastrophe orchestrated by Lucifer. Despite the potential risks involved, Dean struck a bargain at the crossroads to bring Sam back to life following his demise at the hands of one of Azazel's psychic minions. This fateful decision sealed Dean's own fate, consigning his soul to the depths of hell.

By the conclusion of season 3, Dean's fate was sealed, despite Ruby deceiving Sam into thinking he could save Dean. This created an opportunity for the seals to be broken. Among the 66 seals necessary to unleash Lucifer, one required a righteous man to shed blood in hell. In season 4, episode 10, Dean admitted to Sam that he endured unimaginable suffering for 30 long years, succumbing to Alastair and inflicting torment upon the damned souls in hell. As a result, the first seal was shattered, thereby facilitating an easier path to set Lucifer free.

7 Dean Accepted The Mark Of Cain

Although Dean's initial motivation for acquiring the Mark was noble, his impulsive decision had long-lasting consequences throughout several seasons. Despite being aware of the immense burden associated with the Mark, Dean neglected to seek further clarification and instead embraced it to wield the power of the First Blade. His obsessive fixation on eliminating Abaddon, even at the expense of other priorities, reflected his characteristic tendency to prioritize action over thoughtful consideration.

Because of the Mark, Dean grappled with an overwhelming fury that morphed into a disturbing pleasure for murder, as demonstrated when he, Sam, and Jody annihilated a vampire nest. Furthermore, the Mark played a significant role in breeding deception between the brothers, exemplified by Dean misleading Sam to an unconnected location with the intention of eliminating Abaddon. Moreover, his Blade-induced wrath spurred him to assault Gadreel, even though the latter was jeopardizing himself by betraying Metatron to aid the Winchesters. Regrettably, one of the most heart-wrenching consequences of the Mark and the First Blade was that the immense rage and power it bestowed upon Dean led him perilously close to ending Castiel's life.

6 Sam And Dean Resurrected Abaddon

Resurrecting one of the most formidable demons in the show, Abaddon, to fulfill the trials that could seal the Gates of Hell was a crucial blunder that led to the birth of the Mark of Cain. Had it not been for Sam and Dean's ill-advised decision, the concept of this dreaded mark would never have come into existence. The brothers, in their quest to complete the trials, opted to cure a demon, and in doing so, chose Abaddon - who had already been dismembered and laid to rest - inadvertently resurrecting her as a formidable threat once more.

5 Dean Stopped Sam From Closing The Gates Of Hell

Despite Crowley's warning to all demons to stay away from the Winchesters in order to prevent them from completing the trials, the brothers' negligence in leaving the room after resurrecting Abaddon ultimately made them the main contributors to the chaos she unleashed. This not only ignited her vengeful mission to seize control of hell but also resulted in the immense suffering she caused, such as using hunters as bait to reach Sam and Dean and annulling Crowley's demon deals, thus prematurely consigning souls to hell.

Despite overcoming immense grief and difficulties in the first two trials, Dean's decision to go against his previous beliefs was disheartening. The most devastating moment was when he tragically killed Benny, one of the saddest deaths in Supernatural, all for the sake of rescuing Sam (and Bobby's soul) from Purgatory. This heart-wrenching event serves as yet another reminder that Dean's impulsive choices often result in harmful consequences, ultimately leading to the deaths of their loved ones.

Instead of closing the Gates of Hell and greatly reducing the supernatural dangers to Earth, Dean made the decision to save Sam's life instead. Even though he was willing to sacrifice himself for the greater good, Dean prioritized his brother's well-being. Moreover, this choice could have resulted in Crowley reverting to a human state and potentially confined Abaddon to hell, preventing her from wreaking havoc on Earth. By taking this path, it eliminated the opportunity for Dean to obtain the Mark.

4 Dean Said “Yes” To Michael

In a desperate attempt to save his brother (and Jack), Dean made a fateful decision to allow Michael, the powerful Archangel from the apocalypse alternate world, to possess him. Little did he know that this choice would lead to catastrophic consequences. As Lucifer, fueled by Jack's stolen grace, abducted Sam and Jack, Dean hatched a risky plan to defeat Lucifer by becoming a vessel for Michael. Tragically, this decision resulted in numerous deaths. If Dean had let the already-injured Michael perish instead of giving him a boost through possession, the hunters from the apocalypse world would have been spared, an entire city wouldn't have transformed into monsters, and Michael wouldn't have taken control of Garth, who subsequently attacked Sam and Jack.

3 Sam and Dean Insisted Kevin Translate The Demon Tablet

Kevin found himself caught between the Winchesters, both angels and demons, after meeting Sam and Dean. The Winchesters convinced Kevin to translate the tablet, exposing him to danger when the angels were killed by a Leviathan who captured him. After the defeat of the Leviathans, Crowley took Kevin to have the tablet translated. If Sam had stayed connected and aware of Kevin's peril, he could have intervened instead of cutting off ties from his past.

Not only did Kevin have to contend with being constantly targeted by various enemies, but the act of translating the tablet also took a toll on him. Struggling to decipher its contents, Kevin suffered immense mental anguish while isolated from his family. Tragically, Kevin's trust in Sam and Dean led to his demise, as he was killed by Gadreel, who was possessing Sam. Had he been working and living with Sam and Dean in the bunker, Metatron wouldn't have been able to manipulate Kevin as a test of loyalty.

2 Sam And Dean Didn't Try To Bring Back Adam From Hell

When Sam, under the possession of Lucifer, and Adam, under the control of Michael, became trapped in the cage, Castiel managed to rescue Sam but left Adam behind. Despite the recurring theme of family loyalty and the complex dynamics with their half-brother, it is disappointing that they made no effort to save Adam. Moreover, if they had successfully saved Adam, it would have prevented Michael's return in season 15 as he would not have had a vessel to inhabit. Ultimately, Michael betrayed the Winchesters in his desperate quest for God's approval. Interestingly, Adam and Michael formed a bond over their shared lack of a protective family, only for Michael to later reveal that God was responsible for Adam's demise. Had Sam and Dean shown the same urgency in rescuing Adam as they do for one another, it is possible that Adam could have survived.

1 Sam Not Destroying The Book Of The Damned

Following Dean's acceptance of the Mark, Sam's desperate attempt to "heal" him and the ensuing negative hostility resulted in reckless decisions, such as the retrieval of the Book Of The Damned. This formidable tool of witchcraft not only bolstered Rowena's power (who, at the time, was not exactly a dedicated member of Team Free Will in season 10), but also led to Charlie's tragic demise and the unleashing of The Darkness upon the world. Moreover, Dean's merciless execution of the Styne family, who had murdered Charlie in their pursuit of the book, only served to further satiate the Mark's ravenous thirst for blood.

Sam and Dean's relentless pursuit of their own desires has led to the deaths of innocent individuals and the burden of consequences falling upon their loved ones. Frequently, their unbreakable bond has compelled them to make impulsive choices that set off a chain of difficulties and introduced complex storylines and adversaries that persisted throughout various seasons. Nevertheless, if Supernatural had not placed Sam and Dean's relationship at the forefront, surpassing all other characters, many of the show's most unforgettable moments, such as the period when Sam lacked a soul or Dean's affiliation with demons, may have unfolded differently.