You know the Winchesters have it rough when it’s difficult to come up with a list of even four allies that have helped the boys along in their fight again the demons and monsters of this world. Some potential allies were cut short before they could really join in the fight – Henrickson, Ronald – and others were helpful while their own lives were threatened by a ghost, but didn’t have much interest in the larger fight – Cassie, the detective from the Usual Suspect, the warden in Folsom Prison Blues. Then there were the fair weathered allies, like Rufus, who just really wanted them to get off his lawn, or Jo, who always struck me as wanting to be a hunter to impress Dean rather than to be helpful until Dean was no longer in the picture.
So who were the people that Sam and Dean could reliably turn to in times of need? Read on to find out the four most reliable allies.
I think of all the dead people who haven’t been resurrected, I miss Doctor Badass the most. He slept on pool tables and drank more beer than was healthy, but in the end, he was a genius who once attended MIT and could rig up a computer to find just about anything. His stint as the Winchesters’ unofficial researcher was cut too short when he was caught in the demon onslaught that ended with the roadhouse in cinders. Even in heaven he was a worthy ally, providing important information to help the boys get out of Zachariah’s trap and to the angel they needed to talk with. And let’s not even get started on his awesome hair.
Poor Ellen. She didn’t want anything more to do with hunting or Winchesters after her husband died on a job with John, but she got roped into helping Sam and Dean all the same. As proprietor of the Roadhouse, she was a constant conduit for information into cases and other hunters. After the Roadhouse burned to the ground, she took up a shotgun and joined the Winchesters in closing the devil’s gate. Eventually she went out on the road with daughter Jo to hunt the ever increasing number of demons walking the Earth, only to go down in a literal blaze of glory as she blew up a hardware store to stop a pack of hell hounds from preventing Sam and Dean from getting to Lucifer. I’m sensing a pattern – perhaps the reason the boys don’t have more allies is because they all end up dying horrible, unnatural deaths.
In my heart, he’s number one, but then I have to remind myself that it took an entire season for Castiel to realize his higher-ups were attempting to launch the apocalypse and that maybe he wasn’t working for who he thought he was. Once he began thinking for himself, though, Castiel stepped up to the challenge of passing off as human (though not succeeding very well) and helping Sam and Dean fight against Lucifer in any way he knew how. This included trapping Raphael in a ring of holy fire, killing off a dozen or more of his brothers and sisters, and losing his connection to heaven and possibly even his grace. He sacrificed everything he knew on a whim to help out the Winchesters and died many times because of it. It should be interesting to see what happens now he’s all powered up and potentially a bigwig in heaven now.
As the boys’ surrogate father figure, Bobby has always been there with a word of encouragement, a clear head to figure out mysteries and a convenient slap to the back of the head when needed. Of all the people who have come into the Winchesters’ lives, Bobby Singer is the only constant presence they’ve had in their adult lives. He’s fought beside them, covered for them while breaking many federal laws, and even died for them. It’s a good thing that resurrection seems to be spreading because those boys are going to need him for this next chapter in their lives.
A few that got left off the list: Pamela, Chuck (the only ally who hasn’t died, but he did disappear at the end of “Swan Song”)… and I think that’s about it. No wonder Sam and Dean have died so many times.