Throughout Supernatural, Sam and Dean Winchester, as well as Castiel, time and time again find themselves in situations that make them more villainous, even if they believe they are doing good or even if they don’t know about it. From Dean being taken over by the Mark of Cain to Sam being possessed, it has happened often.

One of the biggest examples is when Sam got hooked on demon blood. Believing he was doing good, saving the world, stopping the rise of the devil, and killing Lilith, Sam was led astray by Ruby and became incredibly powerful while addicted to the substance, which led him to do many questionable things.

10 Cutting Bobby Out Of His Life

Dean dying and going to Hell at the end of his one year obviously had a terrible effect on both Sam and Bobby, but rather than deal with it together, the two separated.

This was not the fault of Bobby, however, as it was Sam who went off the radar, avoided Bobby’s calls, and was lost to him for a good while. Obviously trying to deal with the Lilith problem, Sam neglected his family, and Bobby deserved better.

9 Ignoring Every Warning Sign

When the Winchester brothers think they are in the right about something or are doing the right thing, they often ignore pretty much everything and everyone who tells them otherwise.

Not Bobby, not Dean, not even the newly introduced angels could convince Sam that drinking demon blood and going along with Ruby’s plans were wrong. No matter how wrong or evil it all seemed, Sam ignored every sign and believed he was in the right, frustratingly so.

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8 Lying To Everyone

Over the course of Supernatural’s fifteen-year run, one of the most common narrative threads throughout each season is one Winchester keeping secrets/lying to the other.

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In season 4, it was Sam’s turn to do so, lying about Ruby, about what they were doing together, and about the demon blood at every turn. It is never really good when the brothers lie to each other, and this was one of the worst cases throughout the fifteen seasons in terms of consequences.

7 Trusting Ruby Over His Family

The points about lying and ignoring the warning signs point to one of the most significant issues with Sam’s character during this demon blood storyline.

He trusted Ruby more than Bobby and more than Dean. Yes, there were demons Sam and Dean could, at points, trust like Meg and Crowley, but at the point when Ruby came to the show, every demon experience they had was fairly awful; she was no different. Of course, Ruby did pretty much save Sam’s life, but it was all for her cause, and Sam let his naivety and lust for revenge for Lilith cloud his judgment.

6 Getting With Ruby

Of course, there could be another explanation for Sam’s at points blind trusting of Ruby apart from his desire to see Lilith’s head on a spike; they were sleeping together.

As Sam details to Dean in “I Know What You Did Last Summer,” Sam and Ruby’s connection went well beyond a simple business relationship after Ruby found her new vessel. They undoubtedly have one of the most complex relationships in Supernatural’s fifteen-year run.

5 Attacking Bobby

“When The Levee Breaks” is the tipping point for this whole storyline as Dean and Bobby lock Sam in Bobby’s panic room to try and wean him off of his addiction.

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With the help of Castiel, Sam gets out of the panic room and makes way for one of Bobby’s junkyard cars, only to be met by his father-like figure, who begs him not to go. Sam ends up knocking Bobby out, showing no real remorse for doing so, and driving off.

4 Attacking Dean

In that very same episode, Sam also gets into an altercation with his brother. After leaving Bobby’s, Dean, knowing his brother, hunts Sam down and tracks him to a hotel where they fight.

The whole face-off starts with Dean attempting to kill Ruby, who Sam saves, and Dean pleads with his brother to realize what Ruby is doing. After tearfully calling Sam a brother, Dean gets physically overwhelmed and nearly choked to death by the powerful Sam, who leaves him there despite Dean’s warning that if he leaves, he should never come back, echoing John’s warning years prior.

3 Sucking Blood From A Conscious Nurse

When it came time for Sam to confront and potentially kill Lilith, Ruby makes Sam aware of a minion of Lilith’s who is possessing a nurse and taking babies who can lead them to Lilith.

The two hunt down and kidnap the demon and torture her for information before Ruby tells Sam they need to take her for fuel for Sam as Ruby does not have enough juice. The demon then moves to the nurse’s mind and gives control of the body back to the nurse. That’s an human who is killed and whose blood is drained by Sam.

2 Basically Becoming A Demon

This happens in the season finale, “Lucifer Rising,” moments before Sam confronts Lilith at St. Mary’s Covent, where she waits for Sam.

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Using his power, Sam overpowers Lilith and kills the demons surrounding her. As he edges closer to killing the first-ever demon, Sam’s eyes go black; he ignores the cries of Dean, becoming more monster than he ever had been in the series.

1 Killing Lilith

Then, he kills her. Of course, the killing of such an evil being like Lilith is normally welcomed by the Winchesters, but as Dean found out from the angels earlier in the episode, there were far worse consequences for killing Lilith.

As Zachariah explained to Dean, Lilith was not trying to break the 66th seal to unleash Lucifer; Lilith herself was that seal. When Sam killed her, he opened Lucifer’s cage and brought about the Apocolypse. Of course, he realized his mistakes, Dean killed Ruby, and all was well with the brothers. On top of that, they did stop the Apocolypse, but still, it was a bad move from Sam all around.

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