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5 Worst Things Dean Winchester Ever Did in Supernatural, Ranked

5 Worst Things Dean Winchester Ever Did in Supernatural, Ranked
Image credit: The CW

Dean was no less of a villain than his adversaries.

Throughout the 15 years of Supernatural's run, the Winchester brothers have performed many heroic deeds. However, they left a bloody trail in their wake for every innocent life they saved.

Dean, in particular, never shied away from violence. Despite his heroic efforts, he was often driven by emotions and personal attachments more than Sam. Let's revisit the worst deeds that make Dean Winchester something of a villain of the show.

5. Erasing Lisa and Ben's memories

Dean deeply cared for Lisa and her son, Ben. Crowley exploited this and kidnapped the mother-son duo with the help of his minions. After rescuing them, Dean asked Castiel to erase their memories of him to prevent them from being exposed to supernatural danger.

On the one hand, this was an incredibly noble act. On the other, Dean never asked for their consent, denying Lisa and Ben their agency and the right to choose. But the worst thing is that erasing their memory didn't really change anything. Crowley could still kidnap them to once again exploit Dean's attachment to them. Dean probably should have had Castiel erase his memories of Lisa and Ben instead.

4. Throwing Castiel Out

Yes, we admit that Gadreel cunningly manipulated Dean, but Dean's decision to evict Castiel from the Men of Letters bunker is something we can never forgive. Not only did he show no compassion for his friend, despite all they had endured together, but also, at that moment, Cas had become human and was as vulnerable as the next guy.

3. Lying to Sam about Gadreel

Dean's decision to have an angel possess Sam after his ordeal with Lucifer was wrong on all levels. Furthermore, it affected not just Sam but also Kevin, an innocent bystander. The lie broke Sam's heart, causing trust issues and, to add insult to injury, also resulted in Kevin's poor death.

2. Killing Amy Pond

Even though Amy was a kitsune who devoured people, she did so only to ensure her sick son's survival, and even then, she tried to kill as ethically as possible. Sam felt compassion for her, a sentiment Dean failed to share when he killed Amy in front of her son.

1. Killing Cyrus

The most ruthless act, however, was the murder of Cyrus. Despite being a member of the Frankenstein family, Cyrus was an ordinary boy without surgical enhancements. His only crime was killing the school bully under his sister's pressure. Dean, however, showed no mercy when he shot the teenager in the head.