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WARNING: Only spoilers from Season 4 onwards are whited out.

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Current Main Characters

     Ichabod Crane 

Prof./Capt. Ichabod Crane

https://static.tvtropes.org/pmwiki/pub/images/crane_ichabod_9994.jpg
"I was born more than two centuries ago and my wife is a prisoner in some otherworldly realm. I'm not stranger to complications."
Click to see him as a teenager
Portrayed by: Tom Mison, Andy Pessoa (young)

"Good day. This is Captain Ichabod Crane, Esquire. If you will be so kind, please leave your name, rank, and an address where I may reach you, and I will return this correspondence in a timely manner. And now what do I press? Pound? What's pound?"

A former history professor at Oxford University prior to the American Revolution, Ichabod Crane came to America with the British before switching sides and becoming a spy for the Patriots. Having beheaded the Horseman during a Battle in 1781, he was brought back to life along with the Horseman due to their blood mixing when they both died. Despite his skeptical knowledge of the supernatural in life, he has been an invaluable resource following his resurrection due to his detailed knowledge of supernatural traditions.


  • The Ace: He's easily this among the heroes, being the best in literately everything, be it fighting, being smart, analyzing and searching for information.
  • Action Dad: Is both a father (granted, one in complicated circumstances) and a brilliant fighter.
  • Adaptational Attractiveness: The Ichabod Crane from the original short story is a spindly, lanky, nebbish type, with big ears and a long pointed nose, although still suave and charming enough to be considered attractive. This Crane is played by that guy to the right.
  • Adaptational Badass: To go with his handsome new looks, this Ichabod has gone from a superstitious coward to a centuries-old badass. Even his credentials have been bumped up a bit; from simple country schoolteacher to an Oxford professor of history.
  • Adaptational Heroism: In The Legend of Sleepy Hollow, Ichabod is portrayed as a selfish Gold Digger who wanted to get the daughter and land of a wealthy farmer. This version is far more honorable and selfless and a devoted soldier of justice to the go.
  • Adaptational Nationality: In the original short story, he was American but this version has him being an English defector.
  • Agent Mulder: It helps that, skeptic though he was in his own day, he has...well, let's just say he's seen and been through a lot.
  • Awesome Anachronistic Apparel: His outfits definitely qualify. Justified as he’s shown to have an aversion to modern day clothing.
  • Badass Bookworm: Ichabod was a history professor before he was conscripted.
  • Badass Longcoat: Rarely seen without it as he always wears something evocative from his era.
  • Badass Teacher: Both his original pre-war occupation and his modern-era cover story.
  • Been There, Shaped History: Name an American historical figure or event; chances are that Crane has met them or influenced their outcome in some way.
  • Berserk Button: Modern history's version of the Revolutionary War era, taxes on food, and having to buy water.
  • Big Brother Instinct: He starts looking out for Joe Corbin over the course of Season 3, to the point of giving him relationship advice.
  • Blue Blood: He was part of the English nobility. Didn't really like it, though, and he doesn't miss the fox-hunting.
  • Born in the Wrong Century: Ichabod is uncommonly open-minded and progressive for someone who was born in the 18th century, which is a very good thing when he wakes up in the 21st century and has to work with a black female police officer. He still has trouble adjusting, but he does fairly well for a man who slept through just about every civil rights movement. He was also friends with Native Americans.
  • Broken Pedestal: Played for Laughs with Ichabod and Thomas Jefferson, after the former finds out that the latter not only fathered six children by one of his slaves, but also took a quote of Ichabod's and claimed it as his own. Ichabod initially tries to discount the former as "prurient gossip" until Irving gives him a CliffsNotes on DNA and how it proves Sally Hemmings' children were indeed Jefferson's.
  • Buried Alive: At the end of Season 1. For extra irony, it's his son's former grave.
  • The Chosen One: Ichabod and Abbie are the two Witnesses foretold in the Book of Revelation. After Abbie's death at the end of Season 3, the title falls to Ichabod and Molly.
  • Cultured Badass: Being an 18th-century gentleman, Ichabod has a thing for correct manners as well as works of Latin and Greek; knows Shakespeare's plays well enough to place a quote to its act and scene, and has read Chaucer's The Canterbury Tales in the original Middle English. Also, he's perhaps the best human fighter who can take on and even defeat supernatural creatures.
  • Clueless Chick-Magnet: Handsome, British, moral, intelligent, respectful; in short, a perfect gentleman. Crane has managed to attract the attention of many ladies, both in the present and the past, and has no idea how in either.
    Abbie: She dumped her fiancé for you. Wow. You got some game.
    Ichabod: I neither wanted nor did I invite "game."
  • The Comically Serious: Ichabod is extremely poised despite the modern world's attempt to fluster him.
  • Deadpan Snarker: Can be just as snarky as Abbie. Let's just say:
    Ichabod: Yours isn't the first generation to invent sarcasm.
  • Deal with the Devil: He makes one to get a piece of the Philosopher’s stone in order to strip Dreyfuss of his immortality, at the cost of his soul being forfeited to the devil when he dies. He is optimistic that he can find his way out of it.
  • Defector from Decadence: In this interpretation, Ichabod started out as a British soldier before coming to agree with the American revolutionaries and switching sides.
  • Disappeared Dad: His son, Jeremy, was born after his battle with the horseman and, until "Sanctuary," he didn't even know that he had one.
  • Drives Like Crazy: By Season 2, he has some impressive driving skills, the kind that are more suited to a combat situation than peak-hour traffic.
  • Fish out of Temporal Water: Although he has adapted to a surprising degree. He still doesn't understand or anticipate everything, but he's not floundering and freaking out.
  • The Future Is Shocking: Averted, largely. He takes his time displacement in stride and is more bemused rather than overwhelmed by the changes in American society and technology. However, the plastic packaging on his newly-purchased razor quickly frustrates him, and he is unnerved by computers and the Internet. In fact, what upsets him isn't the things that are entirely strange, but the familiar things that are slightly different, like the fact that you have to pay for water, ten-percent taxes on baked goods, and prices in general.
  • Gentleman and a Scholar: Ichabod was originally a professor before he became a soldier, and retains his high intelligence. He's also a perfect 18th-century gentleman.
  • Gentleman Snarker: See above. Even when dishing out some dry sarcasm, he still maintains his chivalrous and noble composure.
  • Huge Guy, Tiny Girl: Ichabod is at least a foot taller than Abbie.
  • Heroes Prefer Swords: He is exceptionally skilled in literately all forms of combat, be it hand-to-hand, marksmanship, or even using unique weapons, but his greatest specialization appears to be swordsmanship. While he doesn't normally carry or truly own one (he has access to several, but none of them are his), his first choice of a weapon if available would be a sword.
  • Heroic BSoD: Has a noticeable one when he finds out that Abraham is the Horseman of Death. Same thing happens when he finds out his son is dead (or so he thinks...).
  • Iconic Outfit: It's impossible to imagine him without the Badass Longcoat.
  • I Have No Idea What I'm Doing: Abbie lets Ichabod use a computer:
    Ichabod: Lieutenant, I may have done something catastrophic.
  • Large Ham: Occasionally, he's not above big speeches generally referencing the past, often his response when he meets something modern he feels is wrong. Abbie comes to expect it as the seasons go on.
  • Limited Wardrobe: He's always wearing the same clothes he was buried in. In the fifth episode, he asks Abbie if he looks out-of-place in this century; while reassuring him he looks fine, Abbie does say that a change of clothes wouldn't hurt. Two words: skinny jeans. Ichabod is visibly uncomfortable with them and ends up in a similar outfit to his initial one, but keeps his coat. Upon discovering colonial-era historical re-enactors, he purchases several replica costumes to wear as day clothes.
  • Mr. Fanservice: Because there is a perfectly good reason to see Ichabod wet and wearing just a towel. And that reason is Tom Mison's body.
  • My Greatest Failure: Ichabod defected from the British after failing to save Arthur Bernard, the man who showed him the truth about the Secret War, and he's carried that guilt ever since; in fact, that's what Death's been using to keep the two of them linked. In "The Sin Eater," Henry channels Bernard's spirit to help Ichabod let go of his guilt, severing the link.
  • Officer and a Gentleman: An army captain who’s father was a nobleman
  • Omniglot: He speaks several languages, including Greek and Middle English, due to having Photographic Memory.
  • Papa Wolf: In "Sanctuary," when he learns Katrina gave birth to his son, he makes Moloch's minion regret ever screwing with them.
    Ichabod: Give Moloch my regards.
  • Photographic Memory: Although being a physician and a gentleman, learning multiple ancient languages would have been par for the course. The memory just helps explain why he remembers all the myriad tiny details of the mystic stuff happening during the Revolution that are still quite relevant today and why he can draw a map from memory to the exact detail.
  • "The Reason You Suck" Speech: He gives a truly awesome one to Henry in "Awakening," outright calling him "an angry, unruly child."
  • Sealed Good in a Can: Basically what happened to Ichabod in the past; his blood mixed with the Horseman's when he cut off his head, linking them, so Katrina had to put Ichabod into a sort of stasis to keep the Horseman sealed in its own can. However, the Horseman's awakening caused Ichabod to awaken as well.
  • Sesquipedalian Loquaciousness: To Abbie's frequent frustration.
    Abbie: I don't have any idea what that means. Just say "yes!"
  • Sesquipedalian Smith: Compared to his first name, Crane is fairly common.
  • Sherlock Scan: This is a talent of Ichabod's. In "The Sin Eater," from a quick study, he is able to determine the surname of his captor, his lineage, his occupation, and that he is a Freemason.
  • The Snark Knight: For a guy with a vocabulary two centuries out of date, he can handle himself quite well.
  • Supernaturally Young Parent: His son, Jeremy/Henry, is physically an old man while Ichabod himself still appears young.
  • Tall, Dark, and British: Described as such by Jenny.
  • Tall, Dark, and Snarky: Most of Ichabod's snark is aimed at modern inventions and ways.
    Ichabod: (to Abbie) The extent of which your generation has defiled this earth is truly mind-boggling.
  • Trademark Favorite Food: By season 3, donuts have become his favorite food, and among all varieties, maple bacon donuts are his absolute favorites.
  • Troll: The opening to 2x04. Crane spends a few minutes acting terrified to drive...then he pulls some expert-level rally-driver stunts, freaking Abbie right the hell out.
  • Unwitting Pawn: He played right into Henry's hands most of all.
  • Weak, but Skilled: While he is very obviously not superhuman and thus physically inferior to that of the supernatural creatures he hunts, Ichabod can be considered to have reached the peak of human physical conditioning and is also an exceptionally skilled warrior, which makes him able to handle himself. Case to point, he defeated the Horsemen of Death when he was weakened due to being superior in terms of skill and even when Death was at full power, he still puts up quite a valiant fight and manages to outskill him for a decent period of time. He was outmatched by the Pied Piper due to his speed and superior weapon, but managed to cut off his arm and temporarily gain the upper hand due to again having more skill.
  • Worf Had the Flu: His first two losses against Abraham is this: In the first occasion, he had absolutely no intention at all to hurt his friend while Abraham was more than willing to duel him and it's heavily indicated he let Abraham win in the end. In their second duel, Ichabod was reeling from all the buildup to the horrifying truth that Abraham is Death, preventing him from using the full extent of his skills. As displayed in their third duel, Ichabod is more than a match for a weakened Abraham even when he was using his axe.
  • World's Strongest Man: Among human standards in the series, Ichabod is this along with being World's Best Warrior. Already Washington's greatest soldier three centuries ago, in the current modern era, rather than lagging behind the times, Ichabod's skills only kept growing. In a world where many Badass Normal end up getting beaten or killed/incapacitated numerous times, Ichabod has been able to handle himself pretty well and tends to perform feats that would outclass his fellow supernatural-fighting heroes by a rather wide margin. He's survived some of the most grievous of injuries that would have easily killed other human and at some cases is even able to still remain fighting, and has displayed he can take out scores of enemies at once with ease, including supernatural creatures, and the few times he has been beaten in a straight fight are against some of the most hardcore supernatural beings and even then he tends to give quite the fight.

    Jenny Mills 

Jennifer 'Jenny' Mills

https://static.tvtropes.org/pmwiki/pub/images/mills_jennifer_391.jpg
"Remember I told you one time this town was going to go straight to Hell? I hate being right."
Click to see her as an child and teenager
Portrayed by: Lyndie Greenwood, India Scandrick (teenager), Melannie Sanchez (child)

"I have more than faith. I'm a mental patient with a gun."

Abbie's younger sister who was confined in a mental institution. They both witnessed the rise of the Second Horseman when they were children. She briefly broke out of the institution, but has since returned after Abbie assured Jenny that she accepted what they had seen and would work to get her released legally. She eventually told Abbie that she was once possessed by a demon that told her to kill her sister and that she would purposely get herself arrested to protect her. She later takes part in helping to solve the mysteries surrounding the Horseman.


  • Action Girl: She's quite skilled with a gun, and most people struggle to keep up with her in a fight.
  • Adventurer Archaeologist: Almost. The tie-in material mentions she was going to be an archaeology major before fate decided to change her plans.
  • Aloof Dark-Haired Girl: Like her sister, she tends to distance herself from people.
  • Ambiguously Christian: Abbie mentions that her mom had her and Jenny attend Bible classes. Jenny can even recite passages by heart, specifically the Book of Revelation.
  • Big Little Sister: Jenny is noticeably taller than Abbie.
  • Brainy Brunette: She's well-versed on Sleepy Hollow artifacts.
  • Broken Bird: She was also affected by her and Abbie's encounter in the woods, albeit in a different way. Instead of bottling up her emotions and never telling anybody, she confessed what she saw and ended up in an asylum.
  • Brutal Honesty: She's not hesitant to say what she thinks.
  • The Cassandra: She saw Moloch in the woods and knows about the impending Apocalypse, but no one believes her and she's institutionalized because of it.
  • Crazy Survivalist: How she is seen. She's definitely a survivalist, if not crazy. She was also associated with a group of Crazy Survivalists in the past.
  • Dark and Troubled Past: Abbie and Jenny were burgeoning delinquents getting in and out of trouble until their episode in the woods, which separated them and left scars on them both.
  • Deadpan Snarker: Even more so than her sister.
  • Demonic Possession:
    • "The Vessel" shows that a demon named Ancitif possessed Jenny on and off for years.
    • In Season 3, she gets taken over by the "mystical energy" of the Hidden One, an old divine being.
  • Expy: Of Sarah Connor. Jenny is first introduced locked in a mental institution, working out to prepare to fight her enemy. She's also been trained all over the world to prepare for the Apocalypse. She later cuts a hole in the ceiling to get out of her room.
  • Foolish Sibling, Responsible Sibling: Played with. Abbie and Jenny both saw Moloch in the woods. They both went on to become troubled women. Abbie turned her life around while Jenny sank deeper into her "insanity" and stole survival gear in preparation for the End of Days.
  • Foster Kid: Along with her sister. It didn't do any favors for her emotional issues later in life.
  • The Lad-ette: Jenny is a tough fighter and she certainly loves her guns, even quipping that she thinks the guns that Irving loaned her were a gift.
    Irving: Cigars are a gift. Jewelry is a gift.
    Jenny: Maybe I'm a different kind of girl.
  • Little Sister Instinct: In "The Vessel," Jenny reveals that she purposefully got herself institutionalized so that Ancitif wouldn't make her hurt Abbie.
  • The Nicknamer: Ichabod seems to be her favorite target.
  • The Ophelia: Averted. While she was institutionalized after she and Abbie saw the four trees in the woods, Abbie was the one to go into denial and delude herself, while Jenny had the entirely sane reaction of preparing for the upcoming Apocalypse.
  • Promotion to Opening Titles: Promoted to series regular starting in Season 2.
  • Quirky Curls: The "quirky" part coming from the fact that she's seen as paranoid (there's a reason for that) and eccentric.
  • Sibling Team: With Abbie in "The Sin Eater" and "Necromancer."
  • Unresolved Sexual Tension: With Irving, and with Joe. The latter actually gets resolved in "The Art of War."
  • Unwitting Pawn: To Henry in Season 1.

     Diana Thomas 

Special Agent Diana Thomas

https://static.tvtropes.org/pmwiki/pub/images/img_1723_6.jpeg
Portrayed by: Janina Gavankar

A Homeland Security agent based out of Washington D.C. After her partner is killed by a demon, she teams up with Ichabod to find and destroy it. She is also the mother to Molly Thomas who is revealed to be the next Witness who was awakened after Abbie's death. Reluctant to involve her daughter in the war against evil, she takes up the mantle of Ichabod's partner until such a time when Molly is ready to step into the role of Witness.


  • Action Mom: An action-prone Homeland Security agent and is also Molly's mother.
  • Deadpan Snarker: Copes with the supernatural by making dry, cutting remarks. She also is this towards Ichabod and pokes fun at his more eccentric behavior.
  • Defrosting Ice Queen: She starts off distrustful toward Ichabod, and becomes especially hostile once she learns Molly is the next Witness and has a destiny to fight supernatural evil. She eventually comes around and warms to not just Ichabod, but Jenny, Jake and Alex as well when she realizes they are her best chance at preparing Molly for her role and defending herself against any supernatural threats.
  • Face–Monster Turn: In the Bad Future where Malcolm Dreyfuss succeeds in taking over the world, she is forcefully transformed into Malcolm's new Horseman of War.
  • Fair Cop: A federal agent for the US government and also quite easy on the eyes.
  • Mama Bear: Diana's number one priority is protecting Molly and becomes fiercely violent whenever she is put in danger.
  • Suspiciously Similar Substitute: For Abbie. A snarky, no-nonsense badass law enforcement agent with a penchant for skepticism and icy behavior until she slowly starts to defrost due to Crane's influence.

     Jake Wells 

Jacob "Jake" Wells

https://static.tvtropes.org/pmwiki/pub/images/img_1725_0.jpeg
Portrayed by: Jerry Mac Kinnon

A researcher and analyst for Agency 355, the covert organization founded by Washington to combat supernatural evil.


  • Agent Mulder: Even before meeting Ichabod, Diana and Jenny, Jake always kept an eye on news about Sleepy Hollow and the supernatural, and spent a lot of his time in the Vault researching about the secret history of America.
  • Black and Nerdy: A dorky African-American research analyst whose bookworm habits are noted by many others.
  • Dogged Nice Guy: Has a real bad crush on Jenny and tries often to get on her good side, to no avail.
  • Jumped at the Call: When Agency 355 is revitalized by Ichabod and Diana's arrival, Jake is ecstatic that he is finally a part of something that is making a real difference in the world by protecting it from supernatural evil.
  • The Knights Who Say "Squee!": Geeks out when he meets Ichabod for the first time, and is psyched to learn one of his heroes Benjamin Banneker was an ally in Washington's inner circle of monster-fighting Revolutionaries.
  • Mother Nature, Father Science: An Inverted Trope with him and Alex. Jake has an affinity for research on magic and monsters, and specialises in reading arcane symbology and decoding ciphers.
  • Muggle with a Degree in Magic: Doesn't identify as a warlock, but has a natural talent for reading magical languages and using the arcane wards created by Benjamin Banneker.
  • Non-Action Guy: Has no noted combat experience unlike Crane, Diana or Jenny, and tends to work Mission Control.
  • The Smart Guy: Shares this role with Alex on Team Witness. Jake handles research into arcane magic and supernatural history, and is able to quickly pick up on the ciphers Ichabod teaches him to decode the Secret Histories in the Agency's library.

     Alex Norwood 

Alexandria "Alex" Norwood

https://static.tvtropes.org/pmwiki/pub/images/img_1726.jpeg
Portrayed by: Rachel Melvin

A researcher and engineer for Agency 355, the covert organization founded by Washington to combat supernatural evil.


  • Agent Scully: Is more determined than Jake to find a rational explanation for the supernatural happenings in D.C. but tends to fall short when coming across demons, witches and headless horsemen of the apocalypse.
  • Brutal Honesty: In addition to sarcasm, Alex is often blunt and doesn't mince words.
  • Deadpan Snarker: All the time.
  • The Gadfly: Always takes the opportunity to poke fun at someone's expense, her favorite target usually being Jake.
  • Gadgeteer Genius: Alex is your go-to girl if you need to create Magitek out of the many artifacts lying around the vault. She's also very talented in crafting non-magical tech as well.
  • Mother Nature, Father Science: An Inverted Trope with her and Jake. Alex has a keen, scientific mind and specializes in crafting technology, both magical and non-magical.
  • Non-Action Guy: Has no noted combat experience unlike Crane, Diana or Jenny, and tends to work Mission Control.
  • The Smart Guy: Shares this role with Jake on Team Witness. She builds the gadgets and weapons used to fight monsters, and likes to experiment on artifacts kept at the Agency.

     Molly Thomas 

Molly Thomas

https://static.tvtropes.org/pmwiki/pub/images/img_1724.jpeg
Click to see her as an adult
Portrayed by: Oona Yaffe, Seychelle Gabriel (adult)

Diana Thomas's daughter and the next Witness who inherits the responsibility upon the death of Abigail Mills.


  • Future Badass: Her adult self from a Bad Future steals a few tomes from the Vault right under Team Witness's noses, bests Jenny in hand-to-hand combat, and sends Jobe away with a Power Crystal.
  • Kid Hero: The latest in a long line of heroes, with several dozen lives saved, and only eleven years old.
  • Seers: She's chosen the path of the Oracle.
  • The Speechless: When first introduced she's shown to be mute. Diana says two weeks prior (around the time Abbie died) she suddenly stopped speaking and doctors were unable to find out why. She starts speaking again when she meets Ichabod for the first time.
  • Wake Up, Go to School & Save the World: Shades of this are coming out and she's already starting to feel the strain. Again, she's eleven.
  • Wise Beyond Their Years: An intelligent and resourceful eleven-year-old who is a lot more perceptive than people give her credit for. When escaping from the Barghest posing as her father, Molly cottons onto the fact that he isn't who he appears to be and later tricks the beast by leaving behind her hoodie as a diversion.

     Malcolm Dreyfuss 

Malcolm Dreyfuss

https://static.tvtropes.org/pmwiki/pub/images/img_1727.jpeg
Portrayed by: Jeremy Davies

CEO of Dreyfuss Enterprises and the central villain of season 4.


  • Big Bad: Of Season 4.
  • Corrupt Corporate Executive: Had his business partner murdered to have control of the business.
  • Deal with the Devil: Made one of these in the past for business success. His motivation for the first part of Season 4 is to get out of holding up his end of it.
  • Faux Affably Evil: Puts on a front as a charmingly eccentric goofball, but is all too willing to sacrifice human lives in order to achieve immortality.
  • Immortality Immorality: Granted, he was extremely amoral before he became immortal, but he gets much worse after that.
  • Immortality Seeker: Having sold his soul for business success, seeks to use the Philosopher's Stone to gain immortality, in the belief that if he never dies, his soul will never be forfeit.
  • Immune to Bullets: One of the effects of becoming became immortal. However it’s downplayed as he suffers from bullet wounds but will eventually recover with no ill-effects. Subverted when Dina shoots him, after he is stripped of his immortality, as he finds himself that he’s not able to heal himself.
  • Loophole Abuse: Has to lose his soul after his death, so he seeks immortality so that will never happen.

Former Main Characters

    Frank Irving 

Capt. Frank Irving

https://static.tvtropes.org/pmwiki/pub/images/irving_frank_8883.jpg
"This goes without saying, but in your description of events, let's make sure that the perp isn't headless."
Portrayed by: Orlando Jones

"You know, there are two things in life I believe a person should hold on to for as long as possible: virginity and skepticism. Surprisingly, I already lost the first thing, so I'm going to hold on for the second one as long as possible."

The (former) chief of the Sleepy Hollow Police Department (yet affiliated with the New York State Police) who is initially skeptical of Crane and Abbie's assertions. He later discovers the supernatural truth of them when the three of them confront, battle, and trap the Horseman of Death.


  • Action Dad: He has a young daughter, Macey.
  • Affectionate Nickname: Macey is fond of calling him "Popski."
  • Agent Scully: Even more than Abbie. That is, until he finds out what's really going on.
  • Broke Your Arm Punching Out Cthulhu: In "The Akeda," he gets wounded and dies soon after defeating Henry's Animated Armor.
  • Came Back Wrong: Double Subverted. Katrina's spell in "Kali Yuga" says that he is freed of Henry's influence on his soul. However, he also casts no reflection, showing he's not quite human anymore. This is because Katrina's spell was tricked by a magic rune, and Frank really has been spending time under Henry's thrall since his resurrection.
    • Averted by "Awakening," after Henry dies, Irving regains his free will.
  • Da Chief: He was in charge of the Sleepy Hollow Police Department.
  • Deadpan Snarker: It's his way of dealing with all the supernatural craziness all around him.
  • Deal with the Devil: In Season 2, he unknowingly sells his soul to Henry. When he finds out the truth, he isn't happy and immediately seeks a way out of the deal.
  • Did You Just Punch Out Cthulhu?: In "The Akeda," he bests War in a one-on-one swordfight.
  • Empowered Badass Normal: In "The Akeda," he faces off against War, wielding the Sword of Methuselah, and wins. Unfortunately, he sustains a mortal wound and dies.
  • Enemy Within: In Season 2, his soul was tainted by Henry, so he had a sort of alternate personality that served Henry obediently while his true self grew weaker over time.
  • Fair Cop: Hot dad and (former) chief of police.
  • Meaningful Name: He's presumably named after Washington Irving.
  • Not Quite Dead: As shown in "Paradise Lost"'s stinger, he survived his wound in "The Akeda," albeit in ratty clothing and with no shoes, apparently exhausted and wandering alone in Sleepy Hollow.
  • No Ontological Inertia: Henry's binding contract with Irving was voided at the time of Henry's death in "Awakening."
  • Papa Wolf: He doesn't take kindly to demons threatening his daughter. He also takes the fall for the actions of a possessed Macey in the Season 1 finale.
  • Put on a Bus: In Season 3, he is said to have moved away quietly to protect his family from further demonic activity. It's implied that Jenny helped them disappear undetected.
  • Reasonable Authority Figure: In "John Doe," Irving not only deflects questions about Ichabod's qualifications as a police consultant, but makes arrangements allowing Abbie to abduct two quarantined patients from CDC custody based only on her hunch of how to supernaturally cure them. Once he sees the Horseman in action with his own eyes, he's quick to help Abbie and Ichabod.
  • Skeptic No Longer: Once he sees the Horseman with his own eyes, he can no longer insist that the Horseman isn't real.
  • The Snark Knight: A lot of the time, he fills the role of cynical commentator.
  • Tall, Dark, and Snarky: Easy on the eyes and possesses a great deal of snark.

    Katrina Crane 

Katrina Crane, née Van Tassel

https://static.tvtropes.org/pmwiki/pub/images/crane_katrina_414.jpg
"I am a Quaker, sir. I fight for the conviction that every man is free."
Portrayed by: Katia Winter

Ichabod's wife and secret witch who cast the spell to bind Ichabod to the Horseman. She appears to him in dreams in the present, claiming that she is trapped in a place between worlds and can only be freed with the defeat of the Horseman.


  • Adaptational Badass: The source material describes Katrina simply as the daughter of a wealthy farmer. This version is now a witch and the leader of the good coven in Sleepy Hollow.
  • Ambiguously Jewish: She claims to be a Quaker when she first meets Ichabod, but she's shown buried in a Jewish cemetery. Possibly justified in that her maiden name indicates that she's of Dutch ancestry, and Amsterdam had one of the largest, most prosperous, and most assimilated Jewish communities in Europe prior to World War II.
  • Big Good: Was the leader of the Sisterhood of the Radiant Heart, the good coven of Sleepy Hollow.
  • Break the Cutie: Watching her husband sort-of-die and then being trapped in Purgatory by her own coven. And before being trapped, giving birth to a child she can't raise because being associated with her is dangerous for him. Then said child is punished anyway and buried alive, again by her own coven. And when her family is finally altogether after so many years? Her son betrays her to Death for (understandably) causing ALL of his problems and then buries her husband alive in his old grave. Fate itself seems out to get Katrina, and it only gets worse when her own son magically impregnates her with Moloch and she is forced to suffer excruciating pain before she is saved.
  • Burn the Witch!: Katrina was convicted of witchcraft, and though she is still able to contact Ichabod and there's no body in her grave, according to her headstone, she was burned alive.
  • Character Death: In "Tempus Fugit," she's stabbed by Ichabod and dissolves.
  • Damsel in Distress: Katrina can't catch a break as she is first stuck in Purgatory, then captured by the headless horseman. When Ichabod attempts to rescue her, she stays behind so she can relay any information to them. Finally, she needs Abbie and her husband’s help to get rid of her demonic pregnancy.
  • Died in Your Arms Tonight: As Henry/Jeremy is disintegrating, she is seen holding his head.
  • Evil Redhead: As of "Awakening." It took Henry’s convincing to turn to the dark side.
  • Face–Heel Turn: In "Awakening," when she joins Henry in his plan to awaken the witches living in Sleepy Hollow and form a new coven. When Henry is shot and killed by Abbie in the attempt, she goes completely off the deep end and travels back in time to try to kill Ichabod, whom she blames for all of her misery.
  • Guile Heroine: By making sure Ichabod got resurrected, she basically set most of the plot into motion.
  • Hospital Hottie: She was a nurse during the war.
  • Hot Witch: Her husband certainly thinks so.
  • I Have Your Wife: Moloch was holding her hostage in Purgatory as a reward for the Horseman.
  • Inciting Incident: After Henry's death, Katrina casts a spell that transports her consciousness into her past self so she can change things, namely by making sure Ichabod dies in his confrontation with the Horseman.
  • Lady of Black Magic: Graceful, lady-like, and a powerful witch who derives her magic from the elements and can tap into darker forces for stronger, corrupted magic.
  • Love Makes You Evil: After Henry's death in "Awakening," her grief drives her to travel back in time in order to kill Ichabod.
  • Missing Mom: To her son Henry/Jeremy.
  • Mommy Had a Good Reason for Abandoning You: The Sisterhood of the Radiant Heart went after her for messing with Ichabod's fate, and Katrina left the newborn Jeremy with Joseph and Grace Dixon (Abbie's ancestors) so that he didn't have to live life as a fugitive.
  • The Mole: In Season 2, she decides to stay with Headless and Henry to find out more about their plans.
  • Ms Exposition: One of her key roles is to appear and warn Ichabod about whatever evil force is next due to arrive.
  • My Secret Pregnancy: "Sanctuary" reveals that she hid the fact that she was pregnant and secretly gave birth to Jeremy.
  • Mysterious Past: We don't know much about her other than the fact that she was a Quaker, served as a nurse during the war, and used to be engaged to Ichabod's (former) best friend.
  • Never Found the Body: She wasn't in her grave, and it's likely that she was never burned, which means Ichabod has no idea where his wife might lay. Turns out she was in Purgatory, and is brought to the real world in the Season 1 finale.
  • No Good Deed Goes Unpunished: She abandons her son so he can have a better life since she was on the run from her coven. However this lead to her son having a miserable childhood and ends up getting buried alive. This in turn resulted in him becoming a psychopath as one of the first things he does, when he’s reunited with her, is to hand her over to the Horseman of Death.
  • Sealed Good in a Can: Katrina was trapped in Purgatory by her own coven.
  • Significant Green-Eyed Redhead: Due to being the wife of the main character and the one who set many of the show's events into motion.
  • Someone to Remember Him By: She gives birth to a son after Ichabod's fatal encounter with the Horseman.
  • Spirit Advisor: Katrina's soul was trapped in Purgatory by her own coven, but she can occasionally contact Ichabod.
  • Supernaturally Young Parent: Her son, Henry/Jeremy, is physically an old man, while Katrina still appears young.
  • Superpowerful Genetics: Katrina's powers are apparently genetic, as seen by her son, Henry/Jeremy, inheriting her abilities.
  • Unwitting Instigator of Doom: If she hadn't broken off her engagement with Abraham, he and Ichabod wouldn't have dueled and Abraham wouldn't have fallen in with the Hessians, sold his soul to Moloch, become Death, the works. In her defense, she wanted to Marry for Love. Of course, some of this may be the Sharpshooter's Fallacy: if she hadn't so upset Abraham, Moloch probably would have found someone else to be the pale rider's avatar.
  • Unwitting Pawn: To Henry as at one point Abraham tells him suspects that she is somehow getting around the barrier, on where they are staying, that prevents her from using her magic. She briefly talks to Ichabod and Abbie in the mirror before abruptly ending her conversation when she hears a door being open. This allows Henry to spy on Ichabod and Abbie.
  • What the Hell, Hero?: Ichabod calls Katrina out in "The Weeping Lady" for always keeping secrets from him, such as being a spy for Washington, being a witch and, relevant to the episode, covering up the accidental death of Ichabod's childhood friend, whom he was supposed to accompany back to England and marry.

    Abbie Mills 

Agent Grace Abigail "Abbie" Mills

https://static.tvtropes.org/pmwiki/pub/images/mills_grace_abigail_9365.jpg
"I'm trying to hold onto my sanity! Not to mention my job."
Click to see her as an child and teenager
Portrayed by: Nicole Beharie, Jahnee Wallace (teenager), Haley Walker (child)

A life-long resident of Sleepy Hollow, Abbie was about to transfer to the FBI but, due to the changes in the town, she has come to accept her role in the fight against the Horseman as the second Witness to the Apocalypse. Abbie is the driving force in the future of understanding the new Sleepy Hollow. In Season 3, she actually does go to work for the FBI.


  • Action Girl: Facing a badass Mohawk demon, she opts to gun it down.
  • Agent Scully: It's explained as a decades-old habit from childhood, learned in order to defend herself from the twin evils of psychiatry and the foster care system. She gets over it.
  • Aloof Big Sister: To Jenny.
  • Aloof Dark-Haired Girl: She doesn't get close to people. Again, explained by her childhood.
  • Ambiguously Christian: She mentions that her mom had her and Jenny attend Bible classes.
  • Badass Adorable: She's a trained cop and handy with a gun, but she's also cute and tiny with big Puppy-Dog Eyes.
  • Beauty Is Never Tarnished: In her flashback, she was a remarkably cute homeless drug addict.
  • Broken Bird: Abbie is still very much affected by her encounter with Moloch in the woods when she was a kid.
  • The Chosen One: According to Ichabod, Abbie is the second Witness.
  • Dark and Troubled Past: She saw the trees and Moloch in high school, was pretty much ostracized after the fact because of it, then turned to drugs and running with bad people to just try and forget before she was arrested and managed to turn her life around.
  • Deadpan Snarker: She tells Ghost!Corbin to only haunt her if he's going to be helpful.
  • Dead Guy Junior: "Sanctuary" reveals that she's named after her ancestor, Grace Dixon.
  • Do Not Call Me "Paul": Her first name is "Grace," but she prefers to be called "Abbie."
  • Fair Cop: Abbie is a police officer, and attractive.
  • FBI Agent: At the start of the series, she was planning to go to work for the FBI, but puts it off in favor of staying to fight Moloch with Ichabod. During the Time Skip between Seasons 2 and 3, she actually does transfer.
  • Fish out of Temporal Water: In the final act of "Awakening."
  • Foolish Sibling, Responsible Sibling: Played with. Abbie and Jenny both saw Moloch in the woods. They both went on to become troubled women. Thanks to Corbin, Abbie found a better path and became a cop; Jenny, on the other hand...
  • Former Teen Rebel: Used to be a drug-addicted criminal until Corbin convinced her to turn over a new leaf.
  • Foster Kid: Deconstructed. Abbie had a number of problems in her youth (drugs, alcohol, crime) stemming from a lack of a stable home or dependable guardians. She turned her back on Jenny because she didn't want to be put back in the system.
  • Heroic Neutral: She was going to leave Sleepy Hollow for Quantico and not deal with what was going on, but after the events of the pilot, she decides to stay.
  • Heroic Sacrifice: She has a knack for these, pulling off three in just as many seasons. In the Season One finale, she agrees to stay in purgatory so that Ichabod can save Katrina, effectively dooming herself to eternal torment (it doesn't last, fortunately). Then, in the Season 3 mid-season finale, she jumps into a portal with the exploding Eye of Providence, to keep it from destroying Sleepy Hollow, leading to everyone thinking she's dead (this, too, is only temporary). Finally, she gives her life in the season finale to enable the others to destroy Pandora, and it seems like this time, it's going to stick.
  • Huge Guy, Tiny Girl: With Ichabod.
  • I See Dead People: She sees and communicates with Corbin's spirit the end of "Blood Moon."
  • Morality Pet: Possibly to Andy. In "Blood Moon," he appears behind her when she's looking for Serilda but does nothing to stop her.
  • My Greatest Failure: Abbie pretended she saw nothing and let her sister get taken away and committed for insisting they saw a demon in the woods. It nigh-permanently damaged their relationship, to the point where they stopped speaking altogether after ending up on opposite sides of the law.
  • Pintsized Powerhouse: She's only 5'1", but she proves to be more than capable in both shootouts and close-up scraps.
  • Reformed Criminal: She was arrested after trying to rob a pharmacy when she was a teenager, but she's turned her life around since then.
  • Sibling Team: With Jenny in "The Sin Eater," "Necromancer," and "Mama."
  • Unwitting Pawn: To Henry when she decides to stay in purgatory to free Katrina so she can use her magic to stop the Horseman of War from rising. However, it turns out to be useless as War (Henry) was already risen. The real purpose was to separate the witnesses so Henry can break the second seal the apocalypse.
  • Why Did It Have to Be Snakes?: She really doesn't like haunted houses.
  • Working with the Ex: In Season 1, with Luke and in Season 3, with Daniel Reynolds, who becomes her new boss.

     Betsy Ross 

Elizabeth "Betsy" Ross

https://static.tvtropes.org/pmwiki/pub/images/betsy_ross.jpg
"For luck, dear Ichabod."
Portrayed by: Nikki Reed

A contemporary, comrade in arms and former flame of Crane's. Known mostly for sewing the American flag, she was in fact Washington's top covert operative and head of his spy network.


     Joe Corbin 

Joseph "Joe" Corbin

https://static.tvtropes.org/pmwiki/pub/images/joe_corbin.jpg
"I thought my dad's hobbies were fishing and crossword puzzles."
Portrayed by: Zach Appelman

Sheriff Corbin's estranged son.


  • Ascended Extra: He appeared as a one-shot character in Season 2, and was promoted to the main cast for Season 3.
  • Beast and Beauty: He involuntary shape shifts from human to beast when he smells blood. He can only turn human again if he eats human organs. To remove his curse a Shawnee ceremonial chant must be performed.
  • Collateral Angst: Gets somewhat surprisingly killed off in the next-to-last episode in Season 3, according to Word of God solely to provide angst for Jenny, who has to shoot him after he was transformed back into a Wendigo by the Hidden One.
  • Cool Big Sis: Abbie is this to him, due to becoming his babysitter and a substitute daughter to his father when he was nine.
  • In the Blood: Atticus Nevins claims that Gus Corbin was far from an upstanding citizen and alleges that Joe is exactly like his father (which naturally leads to Joe claiming I Am Not My Father, but he seems to have his doubts).
  • Locked Out of the Loop: He tries to get Jenny to tell him more about the stuff his father was investigating, but she refuses to let him get involved because it's too dangerous. She eventually agrees to let him in after he gets kidnapped to get to Jenny.
  • The Medic: After leaving the army, he became an EMT, and is now working at a hospital in Sleepy Hollow.
  • Naïve Newcomer: To the supernatural.
  • Parental Neglect: Corbin often ignored Joe in favor of Abbie and Jenny. Unsurprisingly, that caused some strife between them.
  • The Resenter: Initially, he's rather angry at Abbie, feeling that she stole his father's attention and outright blaming her for the Sheriff's death. Underneath his issues, he does care for her, though, and they make up once the Wendigo business is sorted out.
  • Semper Fi: He's a former Marine. He was given an honorable discharge after being wounded in action.
  • Shell-Shocked Veteran: In his first appearance, he just got back from Afghanistan after his whole platoon was killed and seems to have a pretty bad case of PTSD (granted, partly that was likely because he was cursed to turn into a Wendigo and subsequently ate his comrades).
  • Unresolved Sexual Tension: With Jenny. Actually manages to resolve it in "The Art of War" after some encouragement from Ichabod, leading to a very enthusiastic First Kiss.
  • The Watson: Tends to fall into this role due to being the one least acquainted with the supernatural. He usually manages to combine it with a good bit of snarking, though.
    Joe: So, all we have is a working knowledge of Sumerian, and a very depressing Masonic book?
  • Wendigo: He was transformed into a Wendigo by Henry in Season 2.

     Sophie Foster 

Sophie Foster

https://static.tvtropes.org/pmwiki/pub/images/sophia_foster.jpg
"Trust me, you don't wanna know who I work for."
Portrayed by: Jessica Camacho

An artifact hunter who collides with Jenny and Joe when they search for the stolen Shard of Anubis. Jenny recognizes her techniques as those Corbin used to teach Jenny, though Sophie claims she didn't know him. It later turns out she works for Atticus Nevins, an old friend of Corbin's.


  • Ambiguously Brown: So far, her ethnicity is unclear, but she's probably mixed race.
  • Bitch in Sheep's Clothing: Pretends to be a girl in over her head before double-crossing Jenny and Joe.
  • Con Artist: She pretends to be interested in a hookup with Randall Martin, only to handcuff him in the shower and steal the Shard of Anubis from under his nose. She then plays the innocent hookup once more when Jenny and Joe show up.
  • The Dragon: To Atticus Nevins, a criminal dealing in stolen antiques.
  • Hell-Bent for Leather: Wears a leather jacket and boots.
  • The Rival: To Jenny.
  • The Mole: She's an undercover FBI agent working for Reynolds.
  • Undercover Cop Reveal: Drops her cover to stop Nevins from shooting Joe.
  • Worthy Opponent: Considers Joe and Jenny to be this.

     Daniel Reynolds 

Special Agent Daniel Reynolds

https://static.tvtropes.org/pmwiki/pub/images/daniel_reynolds15.jpg
"Hey, I know you don't see yourself here forever. And if we play our cards right, we can help each other get what we want."
Portrayed by: Lance Gross

Abbie's former classmate from Quantico, who is now her new boss. He's also her ex-boyfriend, which complicates their new relationship.


  • Amicable Exes: He and Abbie were in a relationship while they were both at Quantico, but seem to have separated in good spirits. It still makes their new working relationship a little awkward.
  • Anguished Declaration of Love: Handcuffed to a chair and under the influence of a deadly insect poison that drives him paranoid, he confesses that he legitimately fell for Abbie during their brief relationship. Later he claims not to remember anything that happened after he was stung, and Abbie assures him he didn't say anything out of the ordinary.
  • FBI Agent: He joined the Bureau at the same time Abbie did, and is determined to continue moving up the career ladder.
  • Reasonable Authority Figure: As Abbie's boss, he's often willing to let her act outside of her normal parameters, as he knows she will get results.

     Pandora 

Pandora

https://static.tvtropes.org/pmwiki/pub/images/pandora.jpg
"This does feel like home."
Portrayed by: Shannyn Sossamon

A mysterious woman who has come to Sleepy Hollow for her own sinister reasons, and with her monsters, causes fear and chaos among the townspeople.


    Henry Parrish 

Jeremy Crane / Henry Parrish

https://static.tvtropes.org/pmwiki/pub/images/crane_jeremy_7142.jpg
"I relish any chance to cause my parents pain."
Click to see him as an child and teenager
Played By: John Noble, Braden Fitzgerald (child), Danny Rawley (teenager)

"Now you'll know what it is to lose faith. When it's gone, you have nothing. And when you have nothing, there's nothing holding you back from what you're capable of."

A Sin Eater who helped Crane break the curse connecting him with Death. Later, Parrish was revealed to be Jeremy Crane, Katrina and Ichabod's son, as well as War, the Second of the Four Horsemen of the Apocalypse, bitter over how his parents' actions led to him being trapped in a coffin for two centuries in a state of living death until he was released by Moloch.


  • Amoral Attorney: Starting in Season 2, he begins posing as a lawyer.
  • And I Must Scream: Coupled with Being Tortured Makes You Evil, he was left nearly dead, with his heart stopped, feeding on just the vines that crept into his pine box for two hundred years until Moloch found and resurrected him on the day Abbie and Jenny saw him (Moloch).
  • Antagonistic Offspring: To Ichabod and Katrina. By the end of Season 2, he persuades his mother to join with him in forming a new witch coven, but remains staunchly opposed to his father. In the end, though, he makes amends with both his parents as he dies from a gunshot wound.
  • Bitch in Sheep's Clothing: He's not the gentle old fuddy-duddy he appears to be; he's a ruthless and crafty enemy.
  • Black Eyes of Evil: His eyes turn black whenever he uses his Sin Eater powers and when he's animating his Horseman armor.
  • Blessed with Suck: He has the ability to see the sins of others, but it's taken a hefty psychological toll and led him to become a recluse; although his status as a hermit may have been part of the ruse, he doesn't seem to want to interact with people all that much, even in his real persona.
  • Blood Magic: His blood created the Golem and let him survive the Sisterhood's hex.
  • Break the Haughty: His failure in "The Weeping Lady" results in him breaking down crying. Less from the fact that he's failed, however, than from the fact that he is reprimanded by Moloch. After that, he stops pursuing his own goals, instead just working toward helping Moloch directly.
  • Bullet Dodges You: He manages to stop a bullet fired from Ichabod twice in “Awakening”. However, the second time he stopped a bullet fired from Ichabod, he fails to notice Abbie aiming a gun at him resulting in him getting shot.
  • Chekhov's Gunman: He was the owner of the distorted hand that reached out of the earth when Abbie and Jenny saw Moloch for the first time, as they were witness to his resurrection.
  • Deadpan Snarker: When he reveals his true nature, he becomes much more witheringly sarcastic.
    Ichabod: To begin, let us agree that, through neither your fault nor mine, I was not the most involved father.
    Henry: Oh, my. Is this to be an attempt to start over? Are you going to take me down to the fishing hole?
  • Dead Guy Junior: He was named after his paternal great-grandfather.
  • Deal with the Devil: In Season 2, he tricks Irving into one, gaining possession of his soul.
  • Death Equals Redemption: After he's mortally wounded, he reclaims his birth name "Jeremy" and acknowledges Ichabod as his father.
  • The Dog Bites Back: In "The Akeda," he kills Moloch with the Sword of Methuselah for insulting and disrespecting him and Abraham one too many times.
  • Easily Forgiven: Both Ichabod and Katrina insist that he can be redeemed, even though he's made it very clear that he chose to serve Moloch long long ago. Abbie repeatedly brings up how ridiculous this is, given his many acts.
  • Evil All Along: Henry Parrish is Jeremy Crane, the Horseman of War.
    Henry: War isn't coming to Sleepy Hollow. It's been here waiting all along.
  • The Evil Genius: To Moloch as gratitude for being freed from his coffin by him.
  • Evil Laugh: Since The Reveal, he's been tossing out a sinister chuckle every now and then.
  • Evil Old Folks: He is a rather elderly Horseman of War, and while he almost never fights by himself, instead using his magic or his Animated Armor, he nevertheless proves to still be quick and strong enough to disarm, overpower, and choke his much-younger father (granted Ichabod was caught by surprise).
  • Evil Sounds Deep: Comes from being played by John Noble.
  • Exactly What It Says on the Tin: When Jeremy was resurrected, the church he stumbled upon (the church of Abbie's ancestors) was St. Henry's Parish; he took his name from there. Jenny figures it out, but Headless shoots out her tires, causing her to have an accident before she can tell Abbie.
  • Faux Affably Evil: Henry is charismatic, and often creates a believable façade of a cheerful and kind man, but truly, he is cold, bitter, and cruel. He's good enough to keep the heroes completely fooled right up till he reveals himself in the Season 1 finale.
  • Foreshadowing: A lot of other things make a lot more sense when you realize he was a man Only Mostly Dead for a long time. The episode where he reveals himself also shows a couple of his deliberate hints.
  • Four Eyes, Zero Soul: He wears a pair of thick glasses when doing his scheming and War-stuff.
  • Hates Being Touched: Only out of necessity, though. He's very sensitive to seeing sins and touch only makes it worse. This, however, might have been part of his ruse; after The Reveal, he's willing to use his powers as a weapon.
  • The Heavy: Takes up this position from Abraham in Season 2, as Abraham is focused primarily on keeping Katrina safe with him, whereas Henry is far more active in his fight for the Apocalyptic forces.
  • The Hermit: Henry lived alone and was very much a recluse, seemingly because of his powers. While that may have been part of the reason, the bigger reason is likely to have been because he's the Horseman of War and he's playing a very long game.
  • Humans Are Bastards: He gives Ichabod a speech containing the malice in humans in "Root of All Evil."
  • Legacy Character: His betrayal of Moloch is caused in part by the revelation that there have been other Horsemen of War before him and there will be others after him, making him a valuable but ultimately expendable resource. Henry, who thought that he had a special place at Moloch's side, does not take this well.
  • Luke, You Are My Father: Revealing to Ichabod and Katrina in the Season 1 finale that he is their son was quite a shock.
  • Manipulative Bastard: He outmanuevers our heroes like a pro in the Season 1 finale. Thanks to him, Jenny is nearly killed, Katrina is a captive of Death, Ichabod is buried alive, and Abbie is trapped in Purgatory.
  • Meaningful Name: Henry Parrish, the Sin Eater. It's actually meaningful In-Universe, as he picked this name after the church where he was abandoned as a baby, St. Henry's Parish.
  • Never Found the Body: After stabbing Moloch with the Sword of Methuselah, the only thing left on the ground is a portion of Moloch's head. Henry is nowhere to be seen.
  • Promotion to Opening Titles: After recurring in Season 1, he was promoted to series regular for Season 2.
  • Psychopathic Manchild: Ichabod even calls him "an angry, unruly child" in "Awakening."
  • Sin Eater: He has the ability to see and absorb people's sins.
  • Squishy Wizard: In contrast to the all-action Horseman of Death, he prefers to send his magical armour out to fight for him while he controls it from a safe distance. When forced to go into battle in person, he's still very dangerous due to his great magical power but also clearly hampered by being an out-of-shape elderly man with no real fighting skills and limited physical strength.
  • Tragic Villain: Henry/Jeremy truly has had a tragic life—raised in an abusive orphanage, tormented by powers he doesn't understand with only a living doll for company, and eventually buried alive for two centuries. It's little wonder he's so angry and tortured.
  • The Unfettered: He doesn't bat an eye at trading his mother away or burying his father alive. Considering the fact that he hates them and wants them dead, this isn't surprising. However, when he tricks his mother into holding the baby Moloch, he seems very uncomfortable and seems to have finally found something that he hates having to do.
  • Walking Spoiler: From the Season 1 finale onwards, given that his true identity is War.
  • "Well Done, Son" Guy: To Moloch. Moloch appears not to return any kind of parental feeling and tells him that he's a soldier and should obey rather than think for himself. Tellingly, when Moloch reprimands him at the end of "The Weeping Lady," he breaks down into hysterical tears.
    • In fact, it's Moloch's terrible "parenting" that finally leads Henry to kill Moloch and save his real parents.
  • Wicked Cultured: Very much so.
    Henry: "How sharper than a serpent's tooth it is to have a thankless child." King Lear.
    Crane: Act one, scene four. Our mutual love of words is no coincidence.
    Henry: Perhaps I should thank you for the twinkle in my eye.
  • Xanatos Speed Chess: Every single time something seems to be going against him in Season 2 when he directly works for Moloch, it turns out to be Reconstruction in order to further his plans anyway. By "Heartless," Abbie, Ichabod, and Katrina are Genre Savvy to this.
  • You're Not My Father: To Ichabod and Katrina during The Reveal. He feels bitter resentment towards them, and states that he considers Moloch to be his true father.


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