25 Days of Sam-mas Day #19: 5 times Sam Winchester broke our hearts

Supernatural -- "Plush" -- Photo: Liane Hentscher/The CW -- Acquired via CW TV PR
Supernatural -- "Plush" -- Photo: Liane Hentscher/The CW -- Acquired via CW TV PR /
Supernatural Season 3, Episode 5
SUPERNATURAL — “Bedtime Stories” — Photo credit: Sergei Bachlakov/The CW — Acquired via CW TV PR /

While Sam Winchester has had plenty of funny moments in Supernatural, he’s also had some heartbreaking ones. In fact, it’s broken our hearts to watch him. Here are the five times he broke our hearts the most.

On the 25 Days of Sam-mas, we’ve looked at the times Sam made us laugh. While he’s certainly been funny, Sam Winchester has had some of the most heartbreaking storylines in Supernatural, especially in the earlier days. So for Day #19, I’m looking at the top five moments.

It’s not going to be easy just to pick five. I could do more, but I feel if I do more than five, I’ll start adding them all in and then you’ll be kept here forever! So, I’m pulling out the five times I was devastated for him over the years.

5. When he tried to sell his soul for Dean

Early Supernatural certainly has some sad moments. I know some of you will immediately jump to Sam killing Madison. While that’s sad, there are so many things I hate about that moment in the story. So, I’ll let you into a spoiler — it’s not making this list.

Instead, I want to look at when Sam was completely lost. After Dean went to Hell, Sam was on his own and certainly not coping. At one point, he got completely drunk and summoned a crossroad demon with the intention of selling his soul.

Of course, the demon wouldn’t take. What we got to see was this version of Sam we’d never seen before. He was lost and broken, very much like Dean was when Sam died in “All Hell Breaks Loose.” Yep, it’s definitely one of the saddest Sam moments.

Supernatural — Photo: Jack Rowand/The CW — Acquired via CW TV PR
Supernatural — Photo: Jack Rowand/The CW — Acquired via CW TV PR /

4. When he took over Lucifer

In a way, this is a good moment. We get to see that Sam has the power to take over an archangel, something that we’ve not seen anyone else manage to do. Bobby overpowered a demon, but this was an archangel!

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However, it was a sad moment. Our hearts broke as Sam nodded to Dean and then threw himself and Lucifer into the pit. As Michael!Adam tried to stop him, Sam pulled Adam’s body in with him, damning all four.

Another element that made this so heartbreakingly sad was seeing the flashes of young Dean and Sam in the Impala. They were the things in Baby that brought Sam to the surface and were bittersweet memories.

3. When Sam watches Dean die by Metatron’s hands

There is nothing sadder than seeing a family member die. By Supernatural Season 9, we’d watched the Winchesters die multiple times. Sam had been there when Dean coded in the hospital in the second season premiere and when Dean went to Hell. However, it was Season 9 that really got to us.

As MMetatronslid the angel blade into Dean’s chest, Sam and Dean locked eyes. We just watched in shock just like Sam. There was nothing he could do except be there with his brother at the end.

That did lead to Sam trying to summon Crowley to get his brother back. Chances are he would have offered up his soul to save Dean. He didn’t get the chance but his desperation was clearly there.

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Supernatural — “Sacrifice” — Credit: Diyah Pera/The CW — Acquired via CW TV PR /

2. When he shares his fears of Lucifer

Now it’s time for his most recent sad moment, Supernatural Season 13. In “Various and Sundry Villains,” we learned what being Lucifer’s vessel had done to him. He’d seen Lucifer’s face and there was something that he was keeping hidden within for years.

He was terrified of Lucifer because of it. While it took this long to get to this confession, it was heartbreaking as it happened. Sam didn’t tell his brother or even Castiel. He told Rowena, who had also seen Lucifer’s face and feared the same things.

In this moment, we got the sense of just how much Sam has managed to hide over the years. He continually puts everyone else first and it’s time to focus on him for a change.

1. When he shares his confession

As much as I dislike the start of Season 8 for Sammy, I love it for this moment. At the very end of the season, Sam is going through the final trial. Part of that meant he needed holy blood so he needed to head off to a confessional.

Finding out that Sam’s actions would kill him, Dean decided to stop the trials. In this moment, we saw Sam crumble. He shared his confession to Dean and it was downright heartbreaking. This remains one of the saddest moments of Supernatural ever and certainly Sam’s number one saddest moment.

There is nothing past or present that will stop this being Sam’s saddest moment. See what I did there?

Next. 25 Days of Sam-mas Day 1: What to expect. dark

What do you think the saddest Sam Winchester moment is in Supernatural? Which one pulls at your heartstrings every single time? Share your thoughts in the comments below.

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