25 Days of Sam-mas Day #5: The Supernatural women who have helped shape Sam Winchester

For Day 5 of the 25 Days of Sam-mas, it’s time to look at the Supernatural women who have helped shape Sam as the man he is today. This isn’t just about girlfriends, but about the females who have helped inspire him and help his character grow.

The women of Supernatural have a special place in the fandom. They’ve helped the main characters develop and learn more about themselves and the people they’re around. That’s certainly the case for Sam Winchester, and it’s worth looking at them and how they’ve helped Sam for Day 5 of the 25 Days of Sam-mas.

This isn’t just about the romantic relationships. Sammy has had many women help him gain confidence, grow as a human, and inspire him in hunting. He’s had women who have supported and helped him in times of need.

These characters are in introduction order as all have their own importance throughout the years. I’ll also share what they’ve meant to Sam Winchester.

Mary Winchester

There would be no Sam without Mary. It really is as simple as that.

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When Sammy was just six months old, Mary was killed in a house fire. It wasn’t just any fire, though. She died while Sam was being fed demon blood. It was the start of everything and had Mary not gone into the nursery she would have remained alive.

Sam tried to distance himself from the mother he never knew, but he gained her personality in more ways than one. The two have this need to hunt despite desperately wanting to be out of the game. They want to help people and keep the world safe, while also having the white picket fence and loving partner.

Now that Mary is back from the dead, we learned that Sam’s need to stay distant from his mother was just a defense mechanism. He wanted Mary to need him and call him, but she always chose Dean. Now in Supernatural Season 14, we get to see a mother who is supportive and protective of her boys. For some, it may be too little too late, but for others, it’s just right.

Jessica Moore

We couldn’t forget Jess Moore, Sammy’s girlfriend way back in the pilot episode. In the original pilot, she was going to turn out to be a demon but she was the one that helped to push Sam into hunting again. Her death made Sammy need revenge.

And this started a story of Sam’s guilt for letting Jessica die (he blamed himself after seeing her death) and learning that revenge may not be everything it’s cracked up to be. He called his dad out on putting revenge before family and has routinely talked about how revenge doesn’t soothe anything.

If it wasn’t for Jess’ death, we wouldn’t have this side of Sam. We wouldn’t have got the development that we had, as he figured out that hunting and revenge are most definitely not the same thing.

Sarah Blake

Towards the end of Supernatural Season 1, Sam started to move on from Jess. She would always be in his heart, but he started to let himself have a life. Sarah helped with that.

“Provenance” saw her introduction as she became the first woman Sam took on a date after Jess. She realized that he was nervous and had baggage, but she accepted that and helped him feel at ease.

More importantly, she made it clear that he couldn’t keep living in the past. It was at this point that he knew he didn’t have to feel guilty for moving on.

Unfortunately, Sarah didn’t stick around but I’d have loved a story of Sarah joining the Winchesters. The brothers did eventually catch up with her in Season 8, where she became a victim of Crowley.

Madison

In Supernatural Season 2, another woman came along. She helped Sam continue the journey that Sarah had helped start. Sam allowed himself to move on and Madison became the first woman he slept with after Jess.

Out of all the women, Madison didn’t have the biggest effect on Sam for the long term. After finding out she was a werewolf and there was no cure, she asked Sam to kill her because she couldn’t do it herself. In this moment, Sam stepped up, willing to take sacrifices when he needed to.

Ruby

In Supernatural Seasons 3 and 4, we met Ruby. A demon with a special knife, she instantly formed a connection to Sammy. Sometimes a character’s development isn’t always going to be a positive one for the story. Ruby’s influence over Sammy was definitely one of these times.

At first, it wasn’t easy to tell which side Ruby was on. It was in the fourth season that it was clear. Ruby manipulated Sam, encouraging him to become stronger by drinking demon blood. Making him a blood and power junkie, she continued to encourage him to kill Lilith. She knew he didn’t want to hunt monsters and demons forever.

It was this character that nearly brought an end to the Winchesters’ bond. For a while, they hunted separately because Dean couldn’t trust Sam. In fact, it really wouldn’t be until Season 8 that the two were fully able to move on from it all.

Jody Mills

At first, Sheriff Jody Mills looked like she was just another member of the law enforcement. Oh how things changed. After learning about the supernatural world, she took it all in her stride. Soon, she started covering up for the Winchesters and Bobby and even called them when she needed help.

This is a woman who has been a second mother to the Winchesters, something Sam needed in his life when she was introduced. She’s clearly been a shoulder to learn on when necessary, even if we haven’t seen it on screen.

When it came to Sam stepping up as the leader against the British Men of Letters in Season 12, Jody followed him without question. There was never a doubt that he knew what he was doing and that helped him gain the confidence he needed.

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Charlie Bradbury

While our Charlie may have been the perfect wingman for Dean, she has also been a good influence on Sam Winchester. She’s like the little sister they’d never wanted but now love her to pieces. When stuck in a rut, she’s been the one that can help him get through it.

Her death hurt both Winchester brothers and drove a wedge between them. However, times have moved on and now we have Apocalypse Charlie.

This isn’t the same Charlie, but we do get to see the memory of our Charlie inside Sam. We see the love and respect that he’s always had for our Charlie and the new respect he has for Apocalypse Charlie. It’s going to be interesting to see how this dynamic changes in the future.

Rowena McLeod

It can sometimes seem strange to say that Rowena is someone who has helped Sam develop positively. After all, she was initially introduced as an antagonist. However, she has been one of the best things for Sam, especially in recent years.

Rowena is like the crazy aunt that you only see at birthdays and Christmases — and that’s more than enough. When Sam has needed magical help, he’s known that he could rely on Rowena. Of course, sometimes it requires a bargain but others times, it’s simply because she’s fond of Sam and Dean.

Season 13 was a major turning point for Sam and Rowena’s relationship. The two bonded over the fear of seeing Lucifer’s true face. After years, Sam was finally able to let out that fear and those memories. Who would have thought it would have been to Rowena?

Eileen Leahy

Out of all the women on the list, Eileen Leahy is the one that most of us wish could have survived. It’s the ship that most can agree should have happened. But could a romantic entanglement have changed the amazing friendship the two had?

Eileen was a Men of Letters legacy orphaned and deafened as a baby and raised by a hunter. The two had a lot to bond over, including their similar reasons for getting into the hunting game. This was one of those times that learning revenge wasn’t the end came in handy for Sam. He helped Eileen get her revenge but the feeling didn’t change and the two bonded more.

More importantly, Eileen made Sam happy. They could connect in ways that Sam hadn’t connected with anyone else. They made each other laugh and supported each other through emails. When Eileen accidentally killed a British Man of Letters, Sam supported her through the shock. There were hints of the boyfriend that he could still be, something that has been missing for a long time.

Have I missed an influencial woman off the list? Who was your favorite for Sam’s character development? Share your thoughts in the comments below.

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