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In honour of season 11 and all the attitude adjustments it wrought, today we’re counting down some of the top ten “redemption” hits in Supernatural history.

Honourable Mentions

Before diving into the major hitters, we have some honourable mentions that didn’t quite make it onto the final list. These characters either (1) had their turn arounds/revelations off-screen/before meeting the boys or (2) weren’t actively operating against the Winchesters, but rather came to an understanding of something in a brand new way as a result of the Winchester passing through their lives – and for their betterment.

As always, in no particular order:

Bela Talbot

Only just squeaking onto this list in any form or fashion, I ultimately decided to include Bela because it could be argued (albeit loosely) that Ms. Talbot had a deathbed turnaround when she decided to give up the information about Lilith to Dean. True enough, this may have a self-serving end to it, hoping the Winchesters achieve revenge on Lilith that she herself isn’t able to get. On the other hand – deathbed desire for some sense of redemption before going to Hell? Also possible – and enough to earn Bela her place among the HM.


Do we need to explain why he’s here? Our beloved Purgatory pal fell in love and gave up the usual vampire diet – and his clan’s pirate ways – as a result. None of this ended well for Benny, both times it led him back to Purgatory, but once he was committed Benny never drank a person to death.

Anna Milton

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This angel makes the HM list because of her decision to remove her grace and live as a human. Anna was stationed on earth for millennia and came to desire to understand humanity first hand. This was done independent of the Winchesters. Of course, all her actions from the time we got to know her until her death – entirely Winchester related and not for the better in the end.


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It’s hard to make an argument about the redemption of God (then again, this is Supernatural) so let’s just say, he came to a new realization about his sister after talking to the Winchesters and Metatron too. And thank goodness for human kind.

Henry Winchester

Grandpa Winchester is less than thrilled to discover his grandsons (and son) are hunters. Why doesn’t he like hunters? Mostly it’s the “…the unthinking, unwashed, shoot-first-and-don't-bother-to-ask-questions-later part” that bothers him. After he’s spent time with Sam and Dean, he’s changed his mind, at least about his own blood – after all, they are Winchesters, right?

Hit "Next" to see The Top 10 Redeemed Characters...

Hit List: Top 10

Okay, now that we’ve go the “almost/not-quite” out of the way, here we have our main list. Before we get started, let’s lay down the criteria:

a)       No main characters – because let’s be honest if we included the guys in this, they’d be the list. It’s just too easy. So Sam, Dean and Cas are going to sit this one out – at least for now.

b)      Characters we are examining? Those that enjoyed a major attitudinal/perspective shift landing them squarely on Team Winchester

c)       The initial behaviour/attitude/beliefs were not due to a spell or possession or any other like-magical influence

So, in no particular order:

Gabriel a.k.a. The Trickster

Yes, we loved him before we knew he was an archangel – and we love him still, holding onto the hope that he isn’t really dead. But it took a lot for our favourite mischief maker to really commit in the battle of Lucifer v Michael and eventually stand up to his brother Lucifer; even giving Sam and Dean the information they needed to lock Lucifer back up:

“You gotta get the cage open, trick my bro back into it. And uh, oh yeah, avoid Michael and the God Squad. But hey, details, right? And here's the big secret, Lucifer himself doesn't even know -- the key to the cage? It's out there. Actually it's keys, plural. Four keys, well, four rings. From the Horsemen. You get 'em all, you got the cage. Can't say I'm betting on you boys. But, uh, hey! I've been wrong before. And Dean, you were right. I was afraid to stand up to my brother, not any more. [stands up] So this is me, standing up.” – [5.19 Hammer of the Gods]

Victor Henrickson

Most determined to get the Winchesters behind bars and save society from their deadly stain. Intense black and white view of the world, no room for nonsense or crazy supernatural babble. Until a demon possesses him and he shoots the sheriff. Suddenly, Sam and Dean aren’t so serial-killer crazy and the world is a lot more complicated.


Number 2 on Team Metatron back in season nine, Gadreel was desperate to be a hero instead of remembered as the one who let the serpent into the garden way back when. This time around, he was still misled by a slick tongue, but in the end managed to see the error in what he was doing and came to Sam and Dean to offer help fixing the damage. Ultimately, Gadreel sacrificed himself in a desperate act to show Metatron’s true colours to the angels.
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"When they say my name perhaps I will be remembered, not as the one who let the serpent in but as one of the few who helped give Heaven a second chance." – [Do You Believe In Miracles – 9.23]

Meg Masters

One of the most complicated yet straightforward characters on the show, it’s hard to know whether Meg actually fits the aforementioned criteria or not. She started out as an enemy of the Winchesters and ultimately died fighting on their side. Meg was a proponent of choosing a cause and devoting oneself to it entirely – in her case, Azazel and his order was Meg’s passion – which meant once that was no longer something to fight for, then there was something to fight against just the same in all the enemies of that cause. Meg’s...affection…shall we say, for Castiel also changed her along the way – which helped earned her a spot on this list.


The Scribe of Heaven was the inspiration for this list. Nearly up until his death, Metatron was largely self-serving with a disregard for humanity and a deep desire to climb the power ladder. By the end, Metatron has a new respect for humanity – perhaps due to his time as a human – and it motivates him to stand up to both Chuck and ultimately Amara. In a move that surprises everyone enough to have even Dean commenting on it later, a powerless, human Metatron ends up sacrificing himself so Sam, Dean and Lucifer can escape to fight another day.

"I know I'm a disappointment, but you're wrong about humanity. They are your greatest creation because they're better than you are. Yeah, sure, they're weak and they cheat and steal and... destroy and disappoint. But they also give and create and they sing and dance and love. And above all, they never give up." [Don’t Call Me Shurley – 11.20]

Cole Trenton

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Another one of those individuals without enough information, Cole started out under the misconception that Dean was a murderer and set out to extract justice. Unlike Henrickson, this justice involved more blood and less of legal system. Unfortunately for Cole, the introduction to the supernatural world was cruel and still didn’t give him the information he needed about what happened to his father – and still left him gunning for Dean, this time armed with holy water. Ultimately, when Cole came to understand the entire truth and got to know Dean without those black eyes, even being saved by him, he did end up a friend rather than an enemy of the Winchester boys. Though still one of those friends who’d rather not see them ever again.

Jody Mills

A good cop with a low opinion of Bobby Singer – and by extension a disdain for the scam artists posing as FBI she stumbles onto in a diner one afternoon in Sioux Falls. As with many civilians on the list who later learn the reality that is the supernatural world, Jody starts off believing Bobby to be a troublemaking drunk. This quickly changes after a little zombie problem and Jody then becomes one of the best allies in the Winchester arsenal as the series goes on – and one of the dearest friends, loving the boys like a mother would and not afraid to scold them as any good mother would either.


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This angel is another unique situation as this isn’t a simple bad-to-good scenario. In fact, Hannah started out on the proverbial “right” side but was led astray by Metatron and the belief that Castiel should have executed Dean for killing Tessa the angel (those angels and their capital punishment!). It is ultimately Gadreel’s self-sacrificing display that persuades Hannah both he and Castiel are being truthful about Metatron’s motives and she realigns herself with Cas. Later, Hannah’s black and white perspectives still hinder her from time to time, though ultimately her actions inspire Castiel to find Claire Novak.


Balthazar and brother Gabriel had a lot in common: both angels, both enjoyed the more hedonistic style of living and both disappeared from Heaven for a time under the illusion of being dead. Balthazar didn’t want to pick a side in the battle between Castiel and Raphael – though for a time he was on Castiel’s side with all the weapons of Heaven he’d stolen. Eventually, even this fun loving angel came to see Cas was dancing a little to close to the edge and chose the third option – the Winchesters. Sadly, Balthazar was killed for it, but nobody can say the angel who hid away and enjoyed the finer things didn’t finally step up and do the right thing.


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Could we really complete this list without the sister of God? After all she wasn’t defeated, beaten or stopped in the end. Rather, Amara got some clarity of humanity and the world. Maybe it was through her connection with Dean, new understanding of the world after experiencing it first hand, a renewed connection with her brother or a combination thereof: “What you've made, it's beautiful. It took me a long time to see that. I know we can't go back to the way things were. I don't want to. But I wish, I wish we could just be family again.” [Alpha and Omega - 11.23]

So, what do you think? Do you agree with this list? Who did we miss? Make your own list and let us know in the comments!