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The Headless Horseman is Conquest, not Death
The symbols of Death are the scales and a pale horse. The symbols of Conquest are the bow and a white horse. The Horsemen has the latter associated with him, and it would fit since he appeared during Britain's attempt to reconquer the American colonies during the Revolution. It's understandable that they would mistake him for Death, though, considering how good he is at killing.
  • Actually, the scale belonged to Famine, who rode a black horse. In The Bible, Death itself wasn't stated to have any actual weapon besides the Legions of Hell itself.
  • Jossed. Conquest/Pestilence shows up in episode 5.

The Horseman's skull will become a Dismantled MacGuffin
The Horseman will get a hold of its skull, but Abbie or Ichabod will shoot it at the last moment and shatter it into a bunch of tiny pieces. Instead of killing the Horseman for good, it will instead just make it harder for him to regenerate as he now has to reassemble every piece of the skull, with the good guys grabbing a hold of some of them as well.
  • Jossed, for now. It's actually used for the head of the Kindred.

The Horseman's master is Satan himself.
The vague glance we get at him could very well be the guy himself attempting to finish what he started, and the Horsemen are his tools. Even if they're supposed to be neutral parties according to the story, he may hold some sway over them.
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  • Which would make the usage of "Sympathy for the Devil" cross to Fridge Brilliance.
    • Jossed. The Horseman's master is a (lesser?) demon god named Moloch.

Brooks will return in some shape or form.
Although he was taken out as a You Have Failed Me sort of thing, the fact that he was already somewhat of an acolyte of the Horseman means to not count him out just yet.
  • Confirmed; he's been resurrected as a servant.

Sheriff Corbin is really the Horseman's master.
It's common in mythology for demons to be able to change shape, so maybe the demon that controls the Horseman assumed the form of the Sheriff so that it could resurrect the Horseman. When it finally succeeded, it arranged for the Horseman to "kill" it (really just eliminating its human form). It's a sure bet that no one would suspect the deceased Sheriff of being a demon in disguise. This would make for an excellent subversion of Dead Star Walking.
  • Then why was he investigating all the occult cases? If he was the demon, he'd already know all about those.
  • He might have been doing it through some sort of subliminal thing, most likely demonic possession or the evil coven got to him and use subliminal programming to have him to there dirty work.

Captan Irving is a member of one of the covens.
He gets a Traitor Shot in the pilot after finding Abbie in Sheriff Corbin's office. However, it's possible it'll turn out he's actually part of Katrina's good coven, as opposed to the one that serves the demon.

Crane's ranting
Once an Episode, Crane will be complaining to Abbie or someone else about his own personal gripes about the 21st century and/or history and trends after the Revolutionary War, mostly at the beginning after or during the Cold Open. This will include the mathematical inaccuracy stated on the main page. While Played for Laughs mostly, it has the potential to be thought-provoking as well as a nice break from all the weirdness and horror that the show promises. If Crane does not do this at all during an episode, something big is going to happen either during the episode or in the next.
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The "Romani Greek" language name-dropped in Episode 2...
Is just a dialect of Greek used by Romani people living in Greece. Maybe with some loanwords/dialect stuff, more like Yiddish than either language separately. (Why Crane recognizes it and seem to know it is still a mystery, however.)
  • He mentions in the episode how he understands it: He has an eidetic memory, and learned the language before his "death."
    • The problem's not literally how he knows it; it's where he might have learned it—Classical Greek and Latin would be part of a fairly standard education; I can't imagine that a dialect specific to one particular marginalized group ever would be.
  • Oddly, though, he doesn't bat an eye at it being called "photographic memory," despite photographs not being invented for another 100 years after he dozed off. Also, I don't think eidetic memory is enough to learn the intricacies of a language, but it's good enough for him to be a savant as needed.

Crane is wrong about him and Abbie being the two Witnesses.
Or rather, he's half-wrong. Abbie is one of the Witnesses, but it's actually her sister Jenny who's the other one, not Crane. That's why they saw Moloch and the white trees when they were younger.
  • In addition (though we don't know exactly how old they were when they saw it, but...early teens?), that could mean that the seven years of Tribulation are coming to a head right, oh, now.
    • This part is unlikely, given that Abbie says that she doesn't want to die for something she did over ten years ago.

Katrina is lying.
She does have good intentions, but she bound Ichabod and the Horseman on purpose. The Horseman is so strong that her coven wasn't able to put spells on him directly, so they had to tie him to Ichabod and put the stasis spell on Ichabod. She feels guilty about using her husband like that, but it was the only chance they had, and she knew putting Death away was more important than her personal feelings.

Sleepy Hollow exists in the Once Upon a Time Multiverse
Because why not? (Maybe
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Mr. Toad will show up at some point.)

We're in for seven seasons of a show, already plotted, before time runs out and the Apocalypse actually happens.
Crane has mentioned several times that the two Witnesses will have "seven years of tribulations." Given that this show is being penned and produced by the writers of the Star Trek reboot as well as Fringe and regular collaborators with J. J. Abrams, the entire show may have already been plotted. Time will tell if we're in for an experience like Lost or more like Fringe.

Abbie/Crane shippers will be disappointed...
...as Katrina will stay on the side of good and Crane will keep his vows. That is, unless the writers use the standard sci-fi/fantasy/horror episode trope of Love Is in the Air via some sort of spell or Applied Phlebotinum. Other than that? Hope you like UST.
  • Tom Mison recently stated in an interview that Ichabod is in love with Abbie.

Captain Irving is not only a member of a good coven; he's older than he looks.
Maybe Crane wasn't the only hard sleeper in town. Everyone needs a good Plan B...

In relation to the above WMG that Crane isn't a Witness...
Abbie and Jenny are the two Witnesses. Crane is actually the False Prophet.

Crane AND Katrina are Time Lords, or one is a Time Lord and the other is their Companion.
Crane's lived a very long time, as has Katrina. If they're both Time Lords, they'd know they should be running for their TARDISes as soon as tall, dark, and headless showed up on the battlefield. Crane got to his TARDIS in the cave (chameleon circuit works on this one!) and something happened that put him and his ship in stasis. He got out of it some ~250 years later. Katrina didn't make it and was trapped by Moloch in Purgatory.

Katrina is a demon and the Big Bad; she's only opposing Moloch because he stole her job.
She's not trapped at all, and is opposing Moloch because SHE wants to be the one to get the glory of ending the world. Here's what really happened 250 years ago...
  • Before the events of the series, Katrina was the demon who led the evil coven and prepared them for the task of bringing the Apocalypse. Moloch wanted the position for himself and, in the manner of demons, ousted her; during the attempted coup, he tried to kill her, but she fooled him into thinking she was dead and fled to get her revenge.
  • In order to stop Moloch, she begins her own, "good" coven in order to derail his plans, tricking her fellow members into thinking she was trying to stop him for the good of the world when, in reality, she was just pissed that he'd taken her role from her. This explains two things:
    • Why she knows so much about Moloch's plans; they were hers first.
    • Why she bound the Horseman—yes, she 'says' that's because it was all she could do, when really, by binding him she could both keep him out of Moloch's hands, derailing his plans, and keep him 'alive' for when she needed him.
      • This would also explain why it took Moloch 250 years to raise him again; he had to work around the power of a fellow demon.
  • Ichabod arrives on scene—maybe she loves him, maybe she thinks it'd be a lark to corrupt him, maybe she just needs him to maintain her cover, who knows; they meet, get married, and Ichabod heads off to the Revolutionary War. Being his wife, he tells her everything (including his mission) and she decides to become a nurse to keep a closer eye on the situation.
  • When Death is killed by Ichabod, she realizes that, as Ichabod's wife, if the Horseman was ever raised again, she could use her influence over him to let him do the dirty work stopping Moloch's plans with no risk to herself. So she chooses him to be the one who is bound to the Horseman; when he wakes up, pretending to be trapped by Moloch is just extra motivation for Ichabod.
  • Once Moloch is defeated, she steps in with no-one any the wiser, and given the position of trust she'd earned in the lives of the Witnesses, killing/stopping them both would be ridiculously easy.
  • Cue the Apocolypse!

This show is set in a very subtle AU from our reality
Most of the stuff is the same, but where we see historical inaccuracies that can't be explained by a long-time cover-up, that where the two universes diverge ever so minutely.

Like Pestilence (first) and Death (last), the other two Horsemen will have already arrived and been prevented/trapped/defeated somehow in between, as follows:
Conquest (Pestilence) – Roanoke, 1587-1590;Famine – 1609-1610, Jamestown, "The Starving Time";Strife – as Katrina is a Quaker, the Antimonian Controversy, Massachusetts, 1637-1638, and/or the Boston martyrs, 1659-1661;Death – 1775-1781.

Ichabod and Katrina had a child, presumably one he never knew about, and now have descendants
The phantom crying baby and the creepy doll thing in the echo house that Katrina brought Abbie to were references to the bloodline's existence.
  • Confirmed in episode 9. They had a son.

The Oxford professor mentioned in episode "John Doe" is Ichabod's descendant.
Several clues to support this:1. The university confirms that there is Professor Ichabod Crane teaching at the present to Luke Morales in that episode. It's very improbable that someone can set it up, no matter what position they have.2. Ichabod reveals that his father was also a lecturer in Oxford in episode 9.3. Also in episode 9, it's revealed that Ichabod and Katrina had a son.

Related to the above, Katrina Crane is the Woman from Revelations.
Revelations 12:1-5: "A great sign appeared in the sky, a woman clothed with the sun, with the moon under her feet, and on her head a crown of twelve stars. It was with child and wailed aloud in pain as she labored to give birth. Then another sign appeared in the sky; it was a huge red dragon, with seven heads and ten horns, and on its heads were seven diadems. Its tail swept away a third of the stars in the sky and hurled them down to the earth. Then the dragon stood before the woman about to give birth, to devour her child when she gave birth. She gave birth to a son, a male child, destined to rule all the nations with an iron rod...". Katrina's son was the ultimate ancestor of the Second Coming of Christ, which is why the tree demon attacked as soon as he was born. She gave him up not long after she gave birth to him, presumably back to England, and now Ichabod's great-great-grandson is the Oxford professor and unaware of how truly important he is.

Moloch wasn't intending to kill the baby
Why not just kill both Katrina and the child before he was born? Why wait until after he took his first breath? Because the plan was kidnapping and corruption, not murder.

The encounter in the woods decided who would be the Second Witness.
Ichabod was already linked to the Horseman at that point, but the turning point for the Second Witness was when Abbie and Jenny saw Moloch in the woods. If Jenny hadn't said that she'd seen the demon, or Abbie had, their positions in the story would be the other way around.

Abbie isn't the Second Witness; Jenny is.
This is totally Wild Mass Guessing, but every criteria that Abbie meets to be the Second Witness, so does Jenny. Moloch said he touched the Second Witness in the woods. He had both Abbie and Jenny. He also said Ichabod would deliver her soul to him. Moloch only uses the word "she"; he doesn't name her. What if, in trying to protect Abbie, Jenny is left unprotected by Ichabod? Delivering her to Moloch. The only person who pronounced her the Second Witness were Ichabod and Katrina. All the things that entwine their fate do the same for Jenny, her parentage, etc. Jenny has also fought alongside Ichabod. Jenny was the one who said she saw the demon, witnessing it. She also knows more about the supernatural. Moloch also says the Saint's name is a sign - "Jennifer is a feminine given name, a Cornish form of Gwenhwyfar[1] adopted into English during the 20th century.It may mean "white fairy" (from Proto-Celtic *Uindo-seibrā "white phantom"). Despite the name's similarity to the Old English words jenefer, genefer and jinifer, all of which were variants of Juniper used to describe the juniper tree,"(wikipedia) As in the White trees signifying the four Horseman. On that note...

What if Jenny and Abbie are both the Second Witness?
Again both of them meet all of the criteria and both of them were touched by Moloch. Abigail's first name is Grace, as in the unmitigated favor of God. Or...

What if the Second Witness hasn't been decided yet?
What if the tribulations that Sleepy Hollow is now facing is the deciding factor on which Mills girl is the Second Witness? Can anyone tell I just really don't want Abbie to die?

What if Moloch is really Jeremy?
Moloch said that Ichabod didn't know his name, that when he learned it, he would deliver the soul of the Second Witness. What if the coven stopping Jeremy's heart led him to give himself over to The Dark Side in Purgatory? He had killed before inadvertently, he was so powerful that the Four Who Speak As One couldn't stop him alone (they had to kill him with the entire coven at their side). What if his power led to him transforming after siding with evil at the moment of his death? The Horseman of Death was previously human, why couldn't a demon be? That could be why he doesn't want Ichabod killed just yet, why he's also keeping Katrina, in addition to being Death's prize. He wants both of his parents to suffer for not protecting him. Moloch has never been seen before Katrina gave birth. We don't know how long she ran from the Four before they delivered her to the "other side," we don't know that Moloch accepted her when she entered Purgatory, only that he's there now. Moloch is the demon of child sacrifice, the witches' sacrificed Jeremy as a child, older, yes, but still a child, human sacrifice, (in a literal way, Katrina, a human, sacrificed the her husband and the raising of her child and parents' tears obviously Katrina and Ichabod have both sobbed buckets over Jeremy) God knows,(pun not intended, but funny now that I typed it.) Jeremy definitely fits all of those requirements.
  • Jossed: Episodes 8 and 9 showed Moloch active long before Jeremy was ever born.
    • Double Jossed with the finale's reveal that Jeremy is both War AND Henry Parrish.

The Second Witness is Captain Irving's daughter
Thus explaining why the demons are targeting her.

Jenny is not dead, but is likely in a coma
While separating the Witnesses might have been the main goal of the finale's events, it seems unlikely that Death would risk sending Abbie an ally, especially one with the knowledge and resourcefulness Jenny has. Plus, as the Horseman of Death, he may be able to deny her death specifically to prevent this.
  • Jossed in the second season premiere.

Katrina married Ichabod because she knew he was a Witness, not because she loved him (although she grew to love him over time)
It's been revealed that we may be meeting Katrina's parents next season, and finding out more about witches. Also, Katrina's Arranged Marriage to Abraham doesn't make sense, considering she's meant to be a Quaker and Abraham is far out of her price range. Theory: Katrina's parents (who are also witches) arranged for Katrina to marry Abraham because his money and position in the Revolution would help them in their fight against evil. However, when she met Ichabod, she somehow realized that he was a Witness, and broke off her engagement to Abraham to marry Ichabod, explaining it to him as "following her heart." In the end, she did genuinely fall in love with him, but it didn't start that way.

Katrina is a whole lot older than she looks.
Not just in that she's spent 200 years in Purgatory, but even before she got trapped she was a lot older than her twenties. Witches are meant to be immortal after all.

Katrina is not just a demon—she's Lucifer.
She's directly connected to two out of the four Horsemen, Death was Abraham, her former suitor, and War is her biological son. It is her actions that helped create Death and War, both directly and indirectly. She was also trapped in Purgatory, not killed in a more normal fashion. She also separated the Witnesses by telling Ichabod and Abbie exactly what needed to be done for one of them to stay in Purgatory and the other one to stay in the land of the living. She is Lucifer, trying to speed the Apocalypse along without overtly interfering because she is somehow locked out of Hell.

In Season 2, Ichabod and/or Katrina will either...
  • Find a way to pull Henry/Jeremy back from The Dark Side and thus redeem him, or...
  • One of both of them will be forced to pull a Mercy Kill on Henry/Jeremy.
    • Jossed. Henry is shot by Abbie and dies in "Awakening."

Ichabod's ex-girlfriend will be the show's version of Bloody Mary.
It's been revealed that Season 2 will feature an ex-girlfriend of his, and her name is Mary. If his former best friend can be the Headless Horseman/one of the Four Horsemen of the Apocalypse, why not have his ex be Bloody Mary?
  • She could be Famine, the only Horsemen we've yet to see. Let's assume Ichabod ending things with her caused her to develop psychological problems that caused her to not eat, or rather caused her to hunger for something other than food to fill the void. Now let's look at the other two Horsemen who's human lives we've seen. Death was created from a dying man and War was created from someone who was angry at people he should have loved instead(All's fair in love and war).

Conquest will appear but will have been created by Moloch's Good Counterpart
The only problem is he will suffer from Heel–Face Revolving Door due to his nature as Conquest, he joins the side that is winning at the moment.

Another character we know will become the last Horseman Famine
This show is getting rather personal so it wouldn't be surprising if someone else is tricked or bound into becoming the last Horseman. Possibles include:
  • Jenny
  • Captain Irving
  • Captain Reyes
  • Katrina (if the bride to the Horseman ritual doesn't work out)

The "Hi Guy" will be a Chekhov's Gunman
You know that weird fat guy that keeps saying "hi" to Crane? Somewhere down the line he might turn out to be a very important agents working for some higher power trying to communicate with Crane, but until then all he can say is "hi". Whether he is yet another agent of Moloch or an agent of God is yet to be seen......

Ichabod and Katrina's marriage will disintegrate when they actually have to be together
They are running on memories. Their experiences have shaped them into different people then who they were when they married. And when they actually have to spend time together, they will realize it.

Season 2 will be entire long Chain of Deals for Henry
It started with Henry hiring Nick to collect the Pied Piper's Bone Flute, so he could crush it into dust, hex it, and send it to Joe Corbin to turn him into a Wendigo. Then, he used Joe Corbin to collect the Jing-Kain return for a cure for the wendigo-ism, which he of course lies about, and then uses it to infect Katrina to be pregnant with Moloch's physical form. Lastly, in case Moloch failed to crawl out of Katrina's womb, which happened, the life-force of said physical form was then collected to be later fed by a succubus Henry summoned to become strong enough to be physical. All this will most likely lead up to Moloch eventually resurrection in the living realm in the season finale.

Season 4 will bring in Alexander Hamilton
Not for any storytelling reason, but with the success of Hamilton they might decide now's as good a time as there ever will be.

With the show moving to Washington,D.C. , Booth and Brennan from Bones may have a harder time missing the supernatural stuff that follows this show around.
  • They managed not to see any weird stuff when they came to Sleepy Hollow, but if things from this show start happening in D.C., it could've got interesting...kinda sad both shows ended.

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