Supernatural: 15 best Sam Winchester moments, ranked

"Hello, Cruel World" - Jared Padalecki as Sam Winchester in SUPERNATURAL on The CW.Photo: Jack Rowand/The CW©2011 The CW Network, LLC. All Rights Reserved.
"Hello, Cruel World" - Jared Padalecki as Sam Winchester in SUPERNATURAL on The CW.Photo: Jack Rowand/The CW©2011 The CW Network, LLC. All Rights Reserved. /
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4. Sam Confesses to Letting Dean Down

It is at the end of the Trials of God, that fans were treated to an excellent moment of character development for Sam Winchester.

As the younger of the Winchester brothers, Sam hasn’t had to make that many hard choices—he literally left Dean in purgatory to live a normal life. On the one hand, that’s exactly what Dean told him to do. On the other hand, why would you not look for your brother even if they said otherwise?

Dean was, unsurprisingly, a little cheesed off at being left to rot in purgatory while Sam lived his life, and this misstep clearly haunted Sam during the Trials of God.

During the third Trial, his body severely depleted, and his mind focused on the task at hand, Sam learns that completing the Trial won’t just close the gates of hell, but will kill him in the process. In a shocking moment that fans will never forget, Sam’s response to this revelation is “So?”.

The Winchesters have always been fighters and they always want to go on living—Sam makes a point of mentioning that at the start of the Trials. But everything that Sam goes through in the course of the Trials makes him realize how many times he has failed Dean.

In fact, his last confession is about his failure to be a good brother to Dean—Sam legitimately believes that Dean would be better off without him because Sam hasn’t done enough to save his Dean.

The entire confessional scene between Sam and Dean is heart-wrenching and powerful—and it’s made all the more memorable by Dean’s valiant attempts to bring Sam back from the edge. That Sam chooses to continue to live and accept his brother’s forgiveness shows just how willing he is to learn more and to grow.

3. Men of Letters = 0, Sam Winchester = 1

Most fans would agree that the British Men of Letters (BMoL) were kind of the worst. They appeared to be allies of the Winchesters—they certainly had the same goals to kill monsters—but they rubbed everyone the wrong way.

But they did have some fantastic gear that made fighting supernatural creatures that much easier—if only it didn’t come with the condescension and a general lack of empathy.

Fans weren’t all that surprised when it turned out that the BMoL weren’t as good as they purported to be. From teaching their young students to game the system by literally murdering their friends, to becoming obsessive about their codes and rulebooks, the BMoL proved that they were just another bureaucratic machine that needed oiling.

While both Dean and Sam went up against the BMoL together, in the end, Sam led their hunter friends in an all-out attack on the BMoL base. Sam had a structured plan—having studied the layout during his time with the BMoL—and was efficient in the execution of the plan.

In the end, the BMoL were demolished, and all remaining Winchesters were reunited—having learned a valuable lesson about whom to trust.

Never one to hold a grudge, Sam even used his time with the BMoL to power his next moves. Sam has always exemplified the Men of Letters legacy of the Winchester family, and he shows as much when he uses some of the BMoL’s techniques to organize his own group of hunters in Season 14.