Freemasons Will Fight the Devil! Fan Theories About Sleepy Hollow

Okay, maybe the Freemasons won’t actually come to fisticuffs with the Devil, but it’s a cool theory! Among the many reasons you should watch Sleepy Hollow is the way the show leaves itself open for theorizing. Each answered question leads to a list of new ones, and given that this is a remarkably fan-engaged show, there have been many Tumblr and Twitter chats about possible paths the show might take on its way to the Apocalypse.


Sleepy Hollow Moloch

A vision straight out of your blurriest nightmares.

Who is Moloch controlling?

Moloch is pretty into sacrifice. From the Hebrew Bible through Allen Ginsburg, he’s always up for a good burnt offering. So why is he the Big Bad for Sleepy Hollow? Could it be that Abbie and Jenny’s parents (or one of the foster families) made a deal to sacrifice the girls for some nefarious gain? What happened during the four days that are missing from Abbie’s memories? In a recent episode Ichabod was infected with an antibiotic-defying illness, while Abbie was not. You could say something about modern vaccinations obviously, but that isn’t fun at all. Beside, this particular illness was supernatural, and had attacked plenty of other modern people in addition to Ichabod and Thomas. This led one fan to ask if Abbie is valuable to Moloch for some reason—this would have been an easy way to get her out of the picture, but instead it is Crane who becomes ill.


Sleepy Hollow Jenny Mills

What is Jenny’s role?

There will be more on this further down, but for now: Who has Jenny been working for? We know that she and Corbin had more of a relationship than we at first thought—seemingly he acted as a surrogate father to both Mills girls. So was he the one who sent Jenny on missions, and if so, how was he funding this and keeping it a secret? Corbin has already visited Abbie once in a vision (although the show kept that ambiguous enough that it could have just been her own wish fulfillment) so is he able to speak from beyond the grave, like Katrina? And if so, does that make him a magician of some sort? What was the connection between Corbin and the priest?


Sleepy Hollow Orlando Jones Captain Irving

Where does Captain Irving fit in here?

What is his deal? At one point Irving says, “Assume I know everything.” This line is buried in an exchange with Luke Morales, a detective who wants to Find Out The Truth About Crane—which will probably become important a few episodes down the line. However, more immediately relevant is his status as Abbie’s ex, and Irving throws this line in Morales’ face to point out that he knows about their prior relationship. It’s played as a throwaway alpha move, but the show’s fans have picked up on the line as proof that Irving knows more than he lets on; given how adept Sleepy Hollow is at layering jokes and double entendre, it would be pretty typical for them to bury an incredibly important clue in an innocuous scene.

So, is Irving part of the battle between good and evil being waged in his precinct? That would explain why he’s giving Abbie and Ichabod so much freedom to investigate crimes on their own. But is he on their side, trying to fight evil, or is he using them as pawns to help Moloch?

Orlando Jones himself is extremely friendly to the fandom, and keeps tabs on it through Twitter. He talked about his favorite theory so far—that Irving is somehow the one who trapped Katrina in the netherworld—but also mentioned a question that keeps popping up: just what was Irving doing in Albany for an entire episode? Was this real, upstate New York Albany, or some sort of nether-Albany?

It’s worth noting as well that the two detectives, Morales and Jones, are working to get transferred into New York City, and that Abbie was about to leave for Quantico when Crane turned up. Sleepy Hollow is clearly not a coveted destination for someone trying to make a name in law enforcement. So the timing of Irving’s transfer to the department (just as things are getting apocalyptic) might imply that he’s more involved with the larger plot than he lets on.


Sleepy Hollow John Cho


OK, honestly, this was mostly just an excuse to post that picture of John Cho’s pez dispenser head, and it isn’t so much a theory as it is a question: where the hell is Andy? And why did he appear behind Abbie in the tunnels under Sleepy Hollow, but then leave her alone to fight Serelda of Abbadon?


Sleepy Hollow Sandman

Freemasons vs. Illuminati:

Ichabod has been working for General Washington in a National Secrets type of way. He engineered the Boston Tea Party and knows about secret passageways beneath Sleepy Hollow. What else does he know? How much did Washington tell him about the secret war between good and evil? And how much is being influenced by Freemasonry? Seriously, I’m asking you. I tried googling “Freemasonry in Sleepy Hollow” and found posts that can only be referred to, legally, as crazypants. There is some imagery common to Freemasonry turning up in the show, and hopes from current Masons that the show doesn’t misrepresent them, but other than that I’m kind of afraid to dig too far into this one. What are your theories, readers? Are the Freemasons going to arm wrestle the Illuminati on Katrina’s grave?


Sleepy Hollow Ichabod Abbie

Ichabbie 4-Eva:

The biggest theory is just that Ichabod and Abbie are destined to be together. I’ve never seen a fandom ship two characters this quickly—between the opening credits and the second commercial break everyone watching went from “will they/won’t they” to “they bloody well better, as soon as humanly possible.” Now on some shows this wouldn’t count as a theory, strictly speaking, but on Sleepy Hollow this leads straight to the ghostly redheaded elephant in the room…


Sleepy Hollow Katrina


She’s got to be up to something. So far the prevalent thread seems to be that she’s not actually the force for good she claims to be. Could she actually be in league with Moloch? Or possibly Ichabod’s extended life was part of a deal she made, which would explain why she’s able to be in a Limbo that Moloch apparently controls? So for all that Ichabod protests his love to Abbie and OnStar NorthStar operators, the fan consensus seems to be that she’s hiding an evil nature, and that when the end comes, she’s going to be implicated.



Who are the Witnesses?

The most interesting theory I’ve found so far, and also the one I agree with is this: Abbie and Jenny are the Witnesses, not Abbie and Crane. Despite Ichabod’s moving assertion, “I do take comfort knowing this strange road we find ourselves on can only be traveled together,” his involvement is tragically accidental, and not part of any destiny. Katrina either made a deal to save him—or possibly to curse him—and now is in limbo because of that. Crane will eventually learn the truth and have to come to terms with the fact that his survival is not ordained, he is not part of a plan, and at that point he’ll have to determine his own role in the battle. Abbie, meanwhile will have to contend not only with her betrayal of Jenny, but also with turning her back on God/faith/destiny/etc. when she denied Moloch’s existence.


So that’s what I’ve come up with so far, now it’s your turn! Where do you think this show is going? How much more batshit can it get? And seriously, what is the connection with the priest?

Leah Schnelbach recently visited Sleepy Hollow, and didn’t find a single evil coven. Get on the ball, people. Follow her on Twitter, evil witches!


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