The Winchesters Just Dropped More Clues About Dean's Role In The Supernatural Spinoff, So Bring On Team Free Will

Dean in the Impala in The Winchesters
(Image credit: The CW)

Spoilers ahead for Episode 9 of The Winchesters Season 1, called “Cast Your Fate to the Wind.”

When The Winchesters brought the world of Supernatural back to the small screen in the fall, there was no guarantee that any of the main characters from the parent series would actually show up. Between the show being set years before Sam and Dean were born and the fact that both brothers were dead by the time the final Supernatural credits rolled, Jensen Ackles’ narration seemed likely to be all that viewers got… but that has definitely not been the case. “Cast Your Fate to the Wind” dropped another clue about Dean that has the Supernatural fan in me back and ready to speculate about Team Free Will again like back in the old days!

Of course, the episode was primarily about John, Mary, and the rest of the team facing a group of vampires (and John coming up with a solution that proved where Dean got his self-sacrificing tendency from), so let’s dig into the clues from “Cast Your Fate to the Wind” about what’s up with the eldest Winchester bro. 

The Latest Clues About Dean In The Past

The first clue of the episode came via Dean’s voiceover, when his future dad was looking at the photo that surfaced in the previous episode and gave a whole new Supernatural twist to the series. While John looked at image of the man who he had no way of knowing was his son, Dean narrated: 

This isn’t how I saw things going when I pushed over that first domino. Thing is, I’ve had more than a few dances with free will and fate. But as my dad used to say, fate is what you make it.

While it’s not quite clear what off-screen Dean means about “that first domino,” any Supernatural fan worth their rock salt knows that he spent over a decade trying to make a stand for free will against fate and predestination. In fact, he was the one to dub himself, Sam, and Castiel as “Team Free Will” back in Season 5, followed by “Team Free Will 2.0” with Jack on board in Season 13. 

If The Winchesters features Dean talking about free will… well, that sure could mean something! Plus, the preview for the next episode at the end of “Cast Your Fate to the Wind” proves that the show isn’t done with dropping Dean into the action. Take a look:

Apparently, the Akrida queen decides that Dean is a hunter and the new goal will be his elimination. She’s not wrong about Jensen Ackles’ character being a hunter, although she obviously didn’t watch Supernatural, or she’d know that Dean has a knack for coming back from the dead… except for the series finale, and Dean’s appearances in The Winchesters even cast the finality of that into doubt!

Why I'm Ready For Team Free Will

Sam and Dean were both dead by the end of Supernatural, and Misha Collins was never seen again on screen after the events of the “Despair” episode sent Castiel to The Empty after confessing his love to Dean. Still, Dean explicitly mentioning free will in the first episode following the one that revealed he was in the 1970s leaves me to at least hope that Team Free Will will be revisited. 

And there is a best-case scenario! With Jared Padalecki (who ultimately supported Jensen Ackles with The Winchesters) starring on Walker elsewhere on The CW and Misha Collins returning to The CW as Harvey Dent for Gotham Knights, I can’t 100% overlook that all three actors for the original Team Free Will will be involved with shows on the network. 

Assuming viewers don't get the best-case scenario, fans probably shouldn't expect the three to be back in their Supernatural roles on the small screen, but the latest clues leave me hoping for at least an audio cameo or either/both getting a mention via Dean’s voiceover. 

Could The Winchesters Really Address Team Free Will?

Of course, this is all speculation with a healthy dose of mostly baseless optimism, but The Winchesters has already proven me wrong when I suspected that the show may have just thrown in an image of Ackles in the winter premiere to try and attract some much-needed Supernatural fans, with no intent to follow through with an actual story. After all, The Winchesters didn’t get an order for a back nine, and Season 1 will stop with 13 episodes. 

Showrunner Robbie Thompson debunked that suspicion to EW, saying that Dean is referred to as “Mystery Man” and “he’s a huge drive for the remainder of the season,” with “more glimpses as we go along.” Thompson also previewed an exciting upcoming development in the season finale when he addressed Dean giving John the letter:

That was something that we talked a lot about early on in the writers' room. That feeling of a sense of both a surprise and inevitability was really exciting. It wasn't quite fixed, you know, when we were going to drop it in the season, but once it landed, it was pretty crazy to see. And we're not just throwing Easter eggs around. This is all building to something that will pay off in episode 13.

Whatever happens in the remaining few episodes of Season 1, it’s clear that there’s a big plan in place. And whether or not Team Free Will even gets a nod, Dean mentioning his “dances with free will and fate” was a fun blast to the Supernatural past, which fans can revisit streaming with a Netflix subscription.

While it remains to be seen whether or not The Winchesters survives the upcoming network bloodbath, you can still find new episodes on Tuesdays at 9 p.m. ET on The CW, and more options on our 2023 TV premiere schedule.

Laura Hurley
Senior Content Producer

Laura turned a lifelong love of television into a valid reason to write and think about TV on a daily basis. She's not a doctor, lawyer, or detective, but watches a lot of them in primetime. CinemaBlend's resident expert and interviewer for One Chicago, the galaxy far, far away, and a variety of other primetime television. Will not time travel and can cite multiple TV shows to explain why. She does, however, want to believe that she can sneak references to The X-Files into daily conversation (and author bios).