A Deeper Look at Season Five Sam Winchester
I so remember this time last year. I was still reeling from Sam’s horrible descent into total darkness, all capped off by his inadvertent kicking off of the apocalypse. These were my exact words at the end of my season four analysis on Sam. “Sam’s only options at this point are redemption, insanity or death. Guess which one I’m rooting for?” We actually managed to see all three of those options in season five and as I had so wished for, the good one won out at the end. Sure it happened in a bittersweet and tragic way, but this show has taught us by now that no outcome is ever pretty for the Winchesters. There is always a price.
Seeing the heart wrenching, stomach turning agony that Sam had to go through to get that long deserved redemption was an ordeal for any fan, but it played out Sam’s tragic story in full circle. He died a hero. He died a martyr. He doomed himself and his soul for all eternity so humanity and more importantly his brother could go on. Well, there was that surprise return at the end, but to me that’s where season six begins, not where season five ends.
Season five for Sam was clearly about doing whatever it took to earn that long awaited redemption. He had to right a wrong, clean up his cosmic mess from season four. Revenge was no longer the goal. That path to redemption required a ton of soul searching and taking a page from the Dean Winchester manual of being a hero. He did it all by enduring the absolute worst physical and psychological torture a man could get. He also had his chance to step out of his brother’s shadow the right way and strengthen their relationship in the process. That renewed brotherly bond only ended up saving the world.
It’s funny how the option of death was removed from the equation for Sam (Dean too). With Lucifer loose, Sam was not allowed to die. He died three or four times (depending on your interpretation) this season and was brought back every single time. So, that Winchester tendency for self sacrifice took on a whole new meaning. His doom wouldn’t end at death. No, he knew he was screwing himself for a whole eternity and did it anyway. In going through this season’s episodes, Sam went through a lot to just get to that frightful end.
Sympathy For The Devil
Sam took about every lump imaginable. The only saving grace was when God saved Sam from Lucifer’s lair he cleaned his demon blood hampered system right up. No painful withdrawal this time, which was good since he had to endure too many other bad things. He wanted to apologize to Dean, to make things right, but big brother wouldn’t let him in. Then “Bobby” berated him as self righteous and reckless and cut off their ties, really hurting Sam in the process. He took it like a man though, accepting he had to take the consequences for his mistake. Then Meg beat on him. Then Zachariah broke his legs and took away his capacity for breathing. He carried on. No, he didn’t buckle until the very end when Dean admitted he didn’t think he could ever trust him again. Yeah, that shattered what little was left of his self confidence and shook him hard for the next several episodes.
Good God Y’all
Oh Sammy. The demon blood addiction may have been physically cleared from his system, but the psychological triggers were still there big time. Combine that overwhelming desire for the power the demon blood brought with Dean’s intense mistrust and Sam couldn’t make sense of things anymore. He realized he was a mess. Of course a lot of that realization came from War, for Horsemen are especially skilled at opening internal wounds and pouring tons of salt and acid into them. Sam’s already injured psyche didn’t stand a chance.
So, when Dean let him go without a fight was Sam relieved or hurt? Both. Sam was in a huge world of hurt. He was confused, lost and needed to step back and re-evaluate his priorities. He also needed someone to understand how he felt and what he was going through. When that person ended up being a Horseman that wanted to end all days and not the person that mattered to him the most, Sam had every right to want to hide his head in the sand and run away from it all. He concluded Dean didn’t want him around and he was too much of a liability to stay. His sadness as he left was overwhelming. He wished things could be different but didn’t know what else to do. Whatever he had to figure out, Dean’s answer made it clear he’d have to do it alone.
Free To Be You And Me
In this episode, I had to wonder what in the world did Sam Winchester do to piss off the cosmos so bad? Did he kick God’s dog in another life? This guy can never ever catch a break. It’s like he’s getting punished for being born.
Sam’s intentions were good. There were demonic omens nearby. He just couldn’t do nothing but he couldn’t step in either. He was too unstable. Naturally, calling in other hunters to go after a swarm of demons proved disastrous. A hunter was killed, the truth about Sam was found out and the remaining hunters went after him. So Sam responded by letting that inner rage fly. That part of him that scared himself so bad he ran. If it wasn’t for a horrified Lindsay staring at him like he was some kind of monster, he would have coldly killed those hunters. So, in another cruel twist, he lets them go and revenge minded hunters gun him down 13 episodes later. Nope, can’t win.
Still, despite the bad events that followed him like a dark cloud, Sam maintained some hope. He found a friend in Lindsay who may have been perplexed by the veil of mystery but still saw the good person underneath it all. She figured out he did some damage because of an addiction and was the first person ever to tell him there was nothing he could have done that was so bad that it couldn’t be redeemed. Even Dean couldn’t do that for him.
What’s remarkable was Sam believed this, which was strange considering the intense amount of self loathing he had going (“Am I going to hate myself any less?”). Sadly, Lucifer knew how vulnerable Sam was and tried hard to crush that hope by playing the dead girlfriend spreading guilt card. He delivered the blow that Sam was his true vessel and he would say yes. Sam couldn’t even kill himself because Lucifer would bring him back. Somehow that ended up strengthening Sam’s resolve. I don’t know how he managed that. He was a lot stronger than he thought.
The End
Sam had a new determination to fight, to get that redemption. He naturally went to Dean for he was smart enough to know he couldn’t do this alone. He was pretty crushed when Dean first turned him away, but humble and grateful when Dean took him back. He was determined not to let Dean down and get his trust back. He also knew about Dean’s stubborn streak and that earning that trust would take some time.
Fallen Idols
This was a really healthy episode for Sam, despite being attacked by Gandhi and Paris Hilton. He finally came clean with Dean. He explained his actions in all of season four in one great sentence. He went with Ruby to get away from Dean. He needed to break out on his own, fulfill his destiny and step out of big brother’s shadow. He wanted to be treated like an equal. He also had a new plan, the only thing they could do now was go out swinging. Dean evenutally agrees, for he too sees how the other way hasn’t been working for them. See Sam, imagine what would have happened if you said that to Dean at the beginning of season four? We would have missed out on some amazing drama, that’s what.
I Believe The Children Are Our Future
The idea here was to reinforce that Sam’s guilt was still burning in full force and he had to believe that someone out there would do the right thing because he didn’t. Anvilicious? Sure. It kind of felt like Touched By A Winchester. But you had to admire the fact that he still had that kind of optimism, especially after all he’d been through. Plus he got to play with Action Figure Castiel. Bonus!
The Curious Case of Dean Winchester
Sam proved he had the patience of a saint. The young guy in the grumpy old men scenario. Both Bobby and Dean didn’t believe Sam could win at cards and tried to protect him. Sam certainly struggled with believing in himself all season but this was an example of how he wasn’t afraid to try. He tried to tell Dean he knew how to bluff and could win fair and square but older brother (much older) instead tried to devise a plan. After Sam emerged victorious thanks to some brilliant bluffing and saved Dean from an aging related death, he passed it off as getting lucky. Talk about selling yourself short. Maybe there were some things about himself he wanted to remain a secret. Sam was indeed proving his worth.
Abandon All Hope
So how did Sam take Ellen and Jo’s death? By handling their losses the way he has with all the others, channeling it into rage. This wasn’t our first sign of Sam’s raging behavior, “Free To Be You and Me” as pretty vivid, but it’s the first time we learn of Lucifer’s desire for that rage inside. It makes him stronger. No wonder hot headed Sammy was destined to be Luci’s vessel. Lucifer easily set off that fire inside Sam during their confrontation and we were left to worry about this major vulnerability in him. After all, angels, demons, it doesn’t matter, they prey on weakness and Sam had plenty.

Alice Jester is the founder, editor-in-chief, head writer, programmer, web designer, site administrator, marketer, and moderator for The Winchester Family Business. She is a 30 year IT applications and database expert with a penchant for creative and freelance writing in her spare (ha!!) time. That’s on top of being a wife, mother of two active kids, and four loving (aka needy) pets.
Just stumbled across this website so I’ve never posted here before but after reading that felt compelled to. Alice, you are a god(ess). Your knowledge of the show and its characters is amazing (and humbling). Unfortunately, I can see myself not getting out of bed for a week while I trawl through the archive! Thanks a million and keep up the excellent work.
I’m so glad this site was recommended to me. I’ve not had the time to read through back articles like I want to but I’m trying to keep up with the new ones. I love everything you said in this article. Sam’s journey has been such sad one.
There were a few season five episodes where I thought opportunities were wasted with both boys but overall I was very satisfied with the whole season and I was glad Sam was able to find the redemption he so desperately wanted although his self-loathing broke my freaking heart!
If Supernatural had ended at the end of season five, I could have lived with it but I’m very excited to see how they continue on and how Sam’s experience in hell will stack up against Dean’s. I can only imagine that spending time with Lucifer was not a walk in the park.
Alice, what can I say – you know how much I love Sam and how much I rooted for him, just as you did – and you paid him a lovely tribute here.
It is bittersweet with the Winchesters, naturally, as there are no happy endings. But there are hardly any in life, and I do hope that the price they – and Sam, as we’re talking about the younger brother – had to pay will somehow, one far day, grant them peace of mind. NOt as long as the show will be on air, probably, as drama sells, but perhaps one day, when the show will come to an end (and I hope that to be in the far, far future) we might see them truly at peace.
Personally, I hope, Sam finds some of it after his great sacrifice.
Thank you, ever again, Jas
P.S: On a selfishly shallow note – thanks for inserting some of my favourite Sam-pictures from the show, as the bar-fight scene in FreeToBeYouAndMe…
Welcome to the site, Tim the Enchanter – always happy to welcome a first-time-poster! Enjoy browsing through the archives… Please, do come back, if you like, and I’m sure I speak for all of us if I say we hope you will feel welcome here and have fun along the ride.
Cheers! Jasminka
Great article, Alice. So sad for Sam. Jas, in real life there ARE happy endings…it’s just that they don’t sell well. People like to watch others that are worse off they are…sad to say. But, we can HOPE for better times for the boys.
Life as a dedicated Sam girl has been rather difficult these past few years. I’ve managed, and I’ve held my ground in the face of adversity, but it’s been tough. But this article really showed why this season is my favorite. Sam’s journey to find redemption is one of the most tragic, heart-breaking, and heroic stories that I have ever witnessed in my life. He had every possible curve-ball thrown his way, and though they sometimes took him down temporarily, he always got back up again, stronger than before. He is a hero in every sense of the word, and while my heart shatters into a million pieces just by thinking about Swan Song, it still fills me with such pride to think about his final sacrifice. Well, not final, since he’s ALIVE!
Thank you for writing this. It’s always nice to see somebody else write a perfect justification for the Sam girls in this fandom! =]
What amazes me in this article is that you describe E-X-A-C-T-L-Y the way I see Sam (in general) and the way I saw him in every episode this season! Thank you!
Alice,
I love your commentaries on the brothers and this indepth look at Sam was what I’d expected…excellent!
You capture so many of my thoughts and even added some new dimenstions (for which I thank you). Like you I saw Sam as standing strong this season and taking the emotional battering that in the past would have had him leaving. He’d always ‘run away’ when he wanted what he wanted and came up against the brick wall that was John Winchester but this time be it Bobby, Castiel, Dean, other hunters Sam came through and took his lumps. Sam truly learned his lesson from Season 4.
The line in Free To Be You and Me from ‘Jessica’ to Sam resonates even stronger in light of Brady’s reveal in The Devil You Know (which I think also alludes to Brady in a circular way) “I was dead the moment you met me.” Well, yes, Jessica but that’s because ‘Brady’ et al were there manipulating things…awful!
Thanks for writing this, I thoroughly enjoyed it.
Sam just kills me. To think back to the boy we saw in the pilot, happy with his girlfiend and a bright future…..sob. He never really had a chance and that is just plain sad. Sam in season 5 knew he was doomed from the first minute of the first episode. But I love that he was able to take all the junk that was done to him and turn it around and use it to save the world. The one thing the angels and demons didn’t take into account when they decided that they were going to use Sam and Dean to end the world was the love between them.
Loved the analysis! I’m a big Sam fan too! So it felt great to have him be the martyred hero of the story!
Glad we have season 6, can’t really get enough.
No, life is not easy for a Samgirl. To start with, my feelings are curiously mixed. I’m so, so proud of Sammy for the sacrifice he made but at the same time my heart is crushed for his horrible fate. Not to mention the really nasty things about him I had to hear in the past and still hear. There are some who think that his sacrifice was “cheesy” and that he got unddeserved credit by doing so. :cry::
That’s why articles like yours are a treasure to me, alice. Thank you so much. 😀
All you Sam girls should be extremely proud of your boy, err, man. For he is NOT that “snot-nosed” little kid that Dean has to protect and keep safe anymore. He made a big, huge mistake at the end of Season 4 (although with good intentions) but he was blinded by his inner demons and his desire for revenge and justice.
Alice, I loved your analysis of our Sam. Very insightful and understanding and it helped me to truly see and understand this very complex character. Although I am a Dean girl, I truly do love Sam and admire and respect him for all that he accomplished this past year. He goofed up, big time, and spent the rest of the year trying to redeem himself not only in the eyes of his brother and others, but redeem himself in his own eyes. Falling is hard, but you can measure the greatness of a man (or woman) by the way they approach the difficult road ahead of him. In Season 4, Sam chose to live the difficult road ahead of him by being drunk, seeking revenge and siding with a demon. However, he learned his lessons and this year he didn’t make the same mistakes and he was able to approach his road to reparation from a more mature viewpoint.
As was pointed out, I do think the beginning of Sam’s turning point to redemption came in Dark Side of the Moon. In that episode he saw what kind of affect his actions had had on Dean. So many times when we are in the depth of pain, we only see our side, we don’t care about anybody else’s side, we only care about our own. In this episode, Sam finally came to the point where he was able to look outside his own pain and see Dean’s pain and understand it and from there he was able to use this knowledge as a stepping stone to getting past the issues that have held him for so long. Dean, however, had not as yet been able to see Sam’s pain because he was too far into the pit of depression and his hole was eating him up. But Sam, well, Sam was awesome here and was finally able to mentally break through his barrier and Dean’s barrier.
We see his continuing growth in 99 Problems and it finally manifests itself in Point of No Return as was so eloquently talked about in your article about the pivotal episode of Season 5. I loved Sam’s moments with Adam, his take-charge attitude, the way Bobby and Castiel now followed his command instead of Deans and then the heartbreaking moments he shared with Dean. Sam showed maturity beyond his years, having learned his lessons and when he says “you’re still my big brother”, well, I still tear up with that comment. It was said so lovingly and respectfully to Dean, of who Dean is to him, that you can’t help but just love this guy. Then finally when his look of utter disappointment in Dean after Dean said Yes, which is the look that ultimately saves Dean, well, one just can’t help but be so proud of this man, who will always be our Sammy. Who saved the day, his brother, his friends and mankind. God Bless Sam Winchester! May he be able to continue to rise above his challenges, forge a new relationship with his brother and become a better and stronger man because of all that he has experienced.
@AndreaW haters will always be haters… Of course every time I read sth bad about Sammy it makes my stomach hurt, but I’m getting over it as time goes by… what really helps is finding out that there are a lot more Sam girls than some people want to believe. Where have you been hiding girls??? 😀
Seriously now, I may be a Sam girl, but i also love Dean very very much and besides that’s what makes me a fan of Supernatural, right? How can you say that you love the show, when you hate one of the brothers??? I have only discovered Supernatural last August and when I started digging the internet about the show, I could have never imagined that there would be a Sam vs Dean war among the fandom and especially that there would be so much hate for Sam (it was after the end of season 4, but as far as I was concerned, that season made me love Sammy even more!!!). So, it was a great shock for me and it’s still giving me a hard time, but in the end who cares? We got what we wanted for our Sammy, right? A redemption, a heroic death and his come back!!! Plus we got our lost bromance back even in that tragic way! Because the brotherly love is the heart of Supernatural!!!
ARIS3, you’re right – one cannot love the show with loving only one brother and hate the other, it does not really get along with the arc of the story, does it? Or if there are indeed people out there who do – I would love to hear how it can be possible.
As I have always been a ‘SamGirl’ from the beginning, I couldn’t imagine not loving Dean, too. Both have a place in my heart, yet in a different way, and I like it that way. I do love the show and I love its theme of standing up to the ones you love – be it blood family or the one that doesn’t end with blood. It’s how I live my life, anyway.
Cheers Jas
Hi Alice
Once again many thanks for all your hard work and for this wonderful analysis of Sam, I guess this was a real labour of love of love for you.
Sams journey through this season was a hard road for him to tread and for us to follow, so many heartbreaking moments, but he was magnificent in Swan Song and I cannot wait to see where the fallout from his huge sacrifice takes us. It has been said before but all you `Sam Girls` have every right to be very proud of your `boy`.
I am also totally confused at how anyone can say they love this show and then claim to `hate` one of the brothers, The Winchesters come as a package!
Poor old sweetheart, if it wasn’t for the bad luck he wouldn’t have no luck at all 😆
I know we’re really all here for the lashings of sado-masochistic gloom but I hope things perk up a bit next season, too much pathos verges on bathos you writer-guys … Give him a break! ( You can still kill him off/beat him up every other episode but you know, with descretion, like … )
Hey Alice,
thank you for taking a deeper look under the surface of Sam and writing it here on this side. I am so grateful for the oportunity to read this analysis and I don`t want to stop. I have to say sometimes when just another hit came in the show against Sam (like the “clap”, or these comercial in CC )I really started to feel angry and wrote sometimes angry words on the CW Board, because I felt like they wanted to show us that every furt in the universe is Sam`s fault. And I was so angry that the writers alienated Sam from all the other people, Bobby, Ellen, Jo, Sam had really almost none connection to others. Even Crowley called him ..what? a rabid dog (or someting similar) that is really hard to take. Knowing where he started in the series as a person who was connected with other people, who wanted ..and lived …a normal life. And this sort of life ..that was Sam..what he wanted…The revelation that Sam (even as a child) was under demonic influence and kept nonetheless so beyond human and softhearted speakes volumes about his character/personality. I feel so sad for Sam when I think, he made new friends, getting teachers and started to have a sort of relationship and ….bam…the higher demons picked them up to manipulate him. I wonder about what they did say or what they tried. Brady for example seemed to be very close to Sam and when the demon possessed him, the demon introduced him to his beloved Jess. The friend “Brady” fell apart and Sam tried to bring him back. And there were more possessed people. It ripped my heart out to see that in the finale. I am…till today…not over it. As much as I love the finale I feel like a big lump is in my stomach and doesn`t get any better although with the knowledge Sam was under this street lamp in the end (and so not in hell or only a short time.
And about brother versus brother fans, that is not me. I love them both, I love their interaction, their emotional fallouts, when they are arguing I understand both…starting to read US Forums (I am from Germany) about SN taught me I have to pay attention, WHERE I read and WHAT and WHOSE comments and I had once a side to read (in the start) where I was terrified about the comments. But I deleted the side from my computer. I thought back then the internet is like a killing field and the Sam bashing brought me even more to take side to this extraordinary charismatic character. But the exploring of Sam is more subtile and silent and not in the forefront, so I think it is wonderful to find such metas. And I brought a few metas already to the CW-Board with the name of the writer and the name of the side. I copied the Dean/Bobby/Sam analyse
Once Sam said that every person has his breaking point. Sam had his breaking point when Dean was shredded to pieces right before Sam`s eyes and went to hell and Sam couldn`t save him. Dean said to Sam: Keep fighting. Sam did..and barely survived and didn`t want to …but he kept fighting in using these powers…now we know he drank blood to get access to the powers, but he kept figthing in his own…way. Sorry if this is chaotic and to long…
Yeah my heart is still shredded to pieces like Dean was from the hell hounds,and I am shredded from Swan Song, but Sam… Sam needed this redemption so badly for himself, so I was relieved for him but …its just to hard to take!
THANK YOU!
Thanks again for a great analysis, Alice. I just had a chance to read your commentary on Dean earlier today, & now read this one on Sam. I am so proud of the character, especially after we discovered that he has been manipulated & basically “screwed” by supernatural forces his entire life. Yet he overcame it all & gained redemption & made that great sacrifice that still brings tears to my eyes just to think about it.
How anyone could call that cheesy is beyond me! I may be slightly more of a Dean girl but I love Sam too. I guess that makes me a Winchester girl, & darn proud of them both!
Hi Alice
Your article was wonderful, so supportive and understanding.
I don’t really have much more to add then what has already been said here.
As much as I could understand and feel for Dean, I could also see Sam’s side as well. All last year I too wondered how Dean was supposed to kill Lillith. I too believed Sam’s powers was the only way to defeat her. I really sympathized and understood why Sam was doing what he was doing. And the price he ended up paying, was heartbreaking.
oh wow! great article!!!^_______^
Great analyse! But I think we can add that Sam was help a lot by surprise in the finale. Lucifer didn’t care about the car, so he didn,t understand why sam got his attention caught by a little soldier and before Lucifer understood what was happening, Sam ”grab him”^^
Leslie92718, it’s always nice to meet a fellow Samgirl. Be welcome. 🙂