Milton Grimm is a centuries-old being who's traveled many places before he founded Ever After High in 1812. These days he serves as the school's headmaster. He treats the students with a favorable destiny better than the ones without, but nonetheless insists that everyone follows the destiny as dictated by their story.
Milton Grimm is voiced by Jamieson Price in English. A child version of Milton Grimm is voiced by Kyle Arem.
Little is known about his days prior to Ever After High, but back then, he and his brother Giles were close. At one point, they met a genie called Gigi Grant and Giles convinced her finder to wish her a friend to accompany her throughout the ages. The result of this was Whisp, who was like a sister to Gigi. That is, until she grew resentful and dangerous. In response, Milton and Giles created a magic mirror to free any finder from Whisp's hold over them.
A long time passed until, in the year 1812, Milton and Giles founded Ever After High. Something happened after this that changed the brothers' relation for the worse and that left Milton in sole control of the school.
As headmaster, Milton is a strict man who insists that no one so much as considers ignoring their destiny. More than any other, he seems to fear that rebellion will lead to the loss of stories and eventually the fairytale figures' entire world. While understandable if true, Headmaster Grimm has no qualms about pointedly ignoring that some students have destinies that are anything but appealing.
He is dressed in a blue coat and light greyish blue vest with a light blue ascot with a golden decoration with a red stone on it. He has green eyes and dark grey hair with a moustache. He also wears a golden ring in the shape of a mirror. He's also rather stout, at least in the stomach area, from the side.
Headmaster Grimm is the brother of Giles Grimm.
Baba Yaga organizes an intervention to get Raven Queen back on the wrong path. Apple, Briar, Madeline, and Lizzie are invited to help, but with the exception of Apple, none are of use. The intervention is ended when a frustrated Raven accidentally turns the headmaster into a chicken-man. Milton fails to get Raven to sign the Storybook of Legends during the Legacy Day ceremony. Knowing what horror this could unleash onto their world, he sneaks off to think of methods to turn the tide. He is interrupted in his ponderings when a dark laugh comes from a mirror in his office.On Headmaster Grimm's orders,
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Milton exploits Blondie's influence over the students by asking her to broadcast about the truth of school legends. Unfortunately, none of the traditional legends hold true. Milton secretly manipulates the results to his liking, with disastrous personal consequences. Milton is writing a speech when C.A. Cupid barges into his office. He is surprised to hear her talk about True Hearts Day and tries to recover the book. He immediately squashes her ideas, forbidding her to speak of the dangerous holiday to anyone, lest it encourages students to break from their destinies. Milton asks questions when he sees C.A. Cupid, Briar Beauty, and Hopper Croakington II going around the school with supplies for a "play". Milton is interrupted during a web conference by Duchess Swan reporting a secret dance to him. Unfortunately, Duchess had been given the wrong directions, so she and Milton walk into a decoy location. Furious, the Headmaster gives Duchess detention. Milton refrains Raven Queen from playing in the Talent Show because Sparrow Hood has already signed up. Also, he is not impressed with her song choice. He attends the Talent Show and is in awe of Raven's capability. Milton agrees with Apple's new idea. Milton is angered by Raven's rebellious acts, but gets silenced by her.
Milton is writing a speech when C.A. Cupid barges into his office. He is surprised to hear her talk about True Hearts Day and tries to recover the book. He immediately squashes her ideas, forbidding her to speak of the dangerous holiday to anyone, lest it encourages students to break from their destinies. Milton asks questions when he sees C.A. Cupid, Briar Beauty, and Hopper Croakington II going around the school with supplies for a "play". Milton is interrupted during a web conference by Duchess Swan reporting a secret dance to him. Unfortunately, Duchess had been given the wrong directions, so she and Milton walk into a decoy location. Furious, the Headmaster gives Duchess detention.Milton summons Raven to his office and does not successfully persuade her to sign. Milton has several flashbacks throughout the time of Thronecoming of his brother and his childhood. He calls for the help of Mrs. Trollworth to switch the Evil Queen's Heritage Hall gift from a wand to a coin. Milton's plan is in action as he finds Raven by the Wishing Well, foreseeing a terrible vision. He is happy for Raven that she wants to sign. He is notified by Cedar that the book is a fake, but doesn't initially believe it. Later at night, he furiously questions the Evil Queen of where she hid the book, but she doesn't say much. He announces the Thronecoming dance and is soon confronted by Apple and Raven, who soon discover that it was he who made Raven into signing the book. He and Giles have a brotherly reunion and reconcile their relationship.
Milton Grimm conducts a Legacy Day ceremony. On the first day of the next school year, he meets with second-year student Raven Queen, asking her about her mother. He removes Muse-ic Class from her schedule and reminds her she must play her part and embrace her destiny. He approves Apple White's request to share a dorm with Raven. Milton conducts Legacy Day practice for the second-year students. Milton asks Apple to keep an eye on her roommate. He leaves his office to catapult cabbages with Dexter Charming, which, unbeknownst to him, is a distraction. He is approached by Apple and they head to his office to chat. Apple shares her worry that Raven is seriously considering not signing the Storybook of Legends. He is disappointed and laments that he cannot force students to do the right thing, only counsel and guide them. He encourages Apple to continue trying to convince Raven of her errors.
- Milton's last name of "Grimm" is a reference to the Brothers Grimm, who collected and standardized many fairy tales starting 1812.
- Milton wears a mirror ring that has a resemblance to the ring worn by the man that found Gigi's lantern and arranged for it to be brought to Monster High. It is yet to be seen if there is a significance to this.