Which Supernatural Characters Could Appear In The Winchesters?

Saving people, hunting things, and tracking down a missing father? Although "The Winchesters" makes many much-appreciated changes to the DNA of "Supernatural," the prequel still shares plenty in common with its predecessor. So why not multiply the fun with the addition of some familiar faces? 

Set in the '70s, "The Winchesters" follows John Winchester (Drake Rodger) and Mary Campbell (Meg Donnelly) as they work to uncover their parents' mysterious past. Their story may take place decades before the events of "Supernatural," but what kind of prequel doesn't find an excuse to throw in some blasts from the past? This world is basically built for these kinds of weird, inexplicable circumstances!

The writers have magic, time travel, and God at their disposal — all of which are great ways to explain how a character from the distant future can appear in this prequel. And based on the words of showrunner Robbie Thompson, that's not an opportunity that "The Winchesters" will be wasting. During an interview with TVLine, Thompson promised fans, "You will definitely see some familiar faces, which I'm super, super excited about." Then, during a virtual press panel (via CBR), he mentioned plans to include "younger versions" of familiar characters.

So far, the only thing set in stone is Dean Winchester himself (Jensen Ackles), who serves as the narrator of this story. But we can also make some educated guesses: with Mary and John on the board, it won't be long before their respective families show up, including Samuel, Deanna, and even the assumed-dead Henry Winchester. Like it or not, we'll almost certainly catch a glimpse of Azazel as well (the yellow-eyed demon who is destined to take Mary's life). But other than folks who organically fit into this story, which familiar faces do we hope to see appear in "The Winchesters"?

Rowena MacLeod

Ten seasons into its run, "Supernatural" realized that something was sorely missing from its formula. What's the point of a paranormal show if there isn't a ruthless and insanely overpowered witch to keep our heroes in check? As the future Queen of Hell, Ruth Connell was so delightful that she kept getting the Winchester treatment — killed off only to somehow return in future episodes. She was a late but essential addition who kept finding fun ways to shake up the story ... often at Sam and Dean's expense. While it probably won't be terribly convenient for them, why not have her do the same for Mary and John?

There's already an opening for Rowena's introduction! The second episode of the series, "Teach Your Children Well," ends with a mysterious hooded figure harnessing the magic of a defeated monster. We never catch a glimpse of their face, but who else loves powerful magic, has fashionably manicured nails, and would be alive in the '70s? Sure, it could just be some other witch, but where's the fun in that?

The only drawback of an appearance from Rowena is the fact that she probably won't be super friendly to the Scooby gang of this prequel. Realizing that power won't bring her happiness and softening the heart to the Winchesters of the world is far off into her future — so the Rowena they meet will be magical, manipulative, and perfectly fine with sacrificing lives for her own gain.

Crowley aka The King of Hell

Speaking of Rowena, we can't forget about her son! Before he answers to the beck and call of his favorite frenemies Sam and Dean, Crowley is a demon who becomes the King of Hell. He commands Hell's army, sends his trusty crossroad demons to collect souls, sics hellhounds on their unfortunate victims, and occasionally partakes in that chaos himself. Should someone sell their soul (a Winchester classic), Crowley could easily worm his way into this story. Much like his mother, it'll be a long time before he finds a reason to make nice with hunters, so he certainly won't be an ally. But if a little danger is the price we have to pay for the suave and sassy presence of Mark Sheppard, then why the hell not?

Castiel ... but which one?

If "The Winchesters" is gonna keep cutting back to Jensen Ackles cruising down the road in his 1967 Chevrolet Impala, then it's only a matter of time before he gets startled out of his narration and back into reality by a gravelly-voiced Misha Collins speaking those infamous words: "Hello, Dean." Where Dean Winchester goes, Castiel usually isn't too far behind. But what's great about Cas is that as an angel, he isn't just limited to joining his old friend in his mysterious liminal space — he could also dip into Mary and John's side of the story, thanks to a little thing called time travel.

Castiel was the character who first introduced the concept of time travel when he, ironically, sent Dean to 1973 to save his young parents from danger. So what's stopping him from retreading that ground by sending either his friend or himself back to the past? And that's not all! There's also a third possibility: as an immortal being, Castiel already exists in Mary and John's present. Unfortunately, it's a much less friendly version of the beloved angel, years before the Winchester bros introduce him to the magical concept of having free will. So if they do meet 1972 Castiel, he'll be nothing more than a soldier in Heaven's army.

But that dire threat aside, more Castiel is rarely a negative and "Supernatural" has some making up to do after his very tragic and disappointing exit from the series. Plus, Misha Collins is already attached to a new CW show, so he might as well take a shuttle on over to the set of "The Winchesters."

Cupid (among other angels)

On the subject of angels, this particular group of God's followers are absolutely obsessed with the Winchesters. Since Sam and Dean have such a crucial role to play in the future apocalypse, they tend to step in whenever something stands in the way of their preferred future. So if Mary or John start veering off the path, we might catch a glimpse of 1972 Castiel or his terrible brothers, like Michael, Raphael, Zachariah, or any of the other angels we love to hate (Balthazar would be fun, but we're not that lucky).

The most likely scenario would be a Cupid. In season 5 of "Supernatural," the brothers cross paths with a cupid who claims to have matched up their parents: "They couldn't stand each other at first. But when we were done with them — perfect couple." Was he lying, or is this a part of the story that really does lie ahead? For all we know, it's already happened. That would explain some of the ways that the story is diverging from the established canon. Whatever the truth, it's only a matter of time before a mostly-naked diaper guy with wings rolls up to wreak havoc on this relationship.

Gabriel aka The Trickster aka Loki

Richard Speight Jr. is currently co-hosting a "Supernatural" rewatch podcast with God (Rob Benedict), so I'm guessing he wouldn't be opposed to a 'Supernatural" reunion. Like the other angels, Gabriel is an immortal being, but while his siblings are known to remain in Heaven, he has no such restraint. Long before this story begins, Gabriel settled among us to cause chaos.

Like their future sons, Mary and John could cross paths with Gabriel under the assumption that he's a Trickster (since he spends his time doling out just desserts to mortals that "deserve" punishment). While they wouldn't actually stand a chance against the archangel, he does have a tendency to fake his death and exit bad situations — so they can at least enjoy the illusion of a win.

Death (or the Future Death)

No one can escape Death ... except the Winchesters, of course. In their series, Sam and Dean escaped Death in every which way possible. They also befriended Death, made an enemy of Death, and eventually, sliced him in half with his own scythe, effectively killing Death. But long before they take down the venerated horseman of the apocalypse, they have to confront him time and time again. Who's to say that Mary and John won't have the same pleasure?

Is all of this just an excuse to see Julian Richings donning his black suit to chow down on some fast food? Perhaps. But it would be well worth the trouble because despite only appearing in a few episodes, Richings' performance made him one of the most interesting characters in the series: powerful, fearsome, and disturbingly dispassionate. He was neither friend nor foe to the Winchester brothers — just a fact of reality that they couldn't help crossing paths with. Given their line of work, the same will be true of Mary and John.

At the very least, the couple ad their friends may end up meeting Death's reapers — including Billie (Lisa Berry), who will eventually take up the mantle of Death herself. On the bright side, she has yet to develop her resentment of Winchesters but then again, seeing a reaper is never a good sign.

Rufus Turner

There are plenty of hunters who become close to the various Winchesters over the years. Bobby will play a crucial role in John's life as a single dad hunter, as will Ellen Harvelle. Since they both become hunters later in life, the odds of crossing paths with them are slim. But Rufus Turner is a rarity: his hunter origins are a mystery, so there's no telling how young he started. Should Rufus cross paths with Mary, John, and the rest of their Scooby gang, we probably won't get the return of Steven Williams. But as a young hunter Rufus would fit right into the group — and we could finally get some details on his backstory.

Jack (or Chuck)

Mary and John's story is diverging from canon in some very significant ways, which means that there could very easily be a God involved in this mess. Both Jack and Chuck are able to bend reality at a whim, and either one of them could be distorting the past. If Chuck is the one responsible, then the Winchesters are in some serious trouble. That would put them up against the biggest "Supernatural" baddie of them all! But since "The Winchesters" has been pretty clever about knowing that bigger isn't always better, this doesn't feel super likely. Where would it even fit into the timeline?

A better explanation is the very friendly spawn of Lucifer, Jack Kline (Alexander Calvert). While he's certainly known to make mistakes with his powers, Jack usually has the Winchesters' best interests at heart. And after accidentally murdering Mary (not her first death, but definitely her last), he kinda owes her one. Maybe all of this is just a misguided attempt to set things right.

Sam Winchester

One of the biggest mysteries of "The Winchesters" thus far lies in the conception of this show: if Dean is narrating this story, then where the hell is he talking from? How does he know all the details? Why is the story playing out differently? And why does Dean hop into the Impala without his brother to sit beside him? 

It's fitting that Dean would be the one to tell this story since he always put their parents on a pedestal and struggled to let go of his perception of their relationship, but that doesn't mean Sam (Jared Padalecki) would be uninterested. And more importantly, this is just plain weird for the pair of brothers who are known to have the world's most worst case of co-dependency! (Sell your soul to resurrect your bother once? Fair enough. But twice? You have a problem.)

Are they separated by some greater force (like death) or has Dean decided to embark on this solo mission for a reason? Honestly, it doesn't matter. If reuniting is an option, then these two will find a way to do it.