Wicked Wonderland: Maddox Hatter

》Basic information 《

Name: Maddox Hatter

Alias: Maddox

Age: 46 years old

Height: 5 feet 10 inches

Gender: Male

》Appearance: Maddox Hatter is an Asian descendant with oval shaped brown eyes and light skin.

In Descendants: The Rise of Red, Maddox cut a striking figure in his plaid top hat, short purple hair, an orange handkerchief, and olive-green leather trench coat worn on top of a pin-striped wool suit.

In Descendants: Wicked Wonderland, Maddox wears the same plaid top hat but has long wavy purple hair with yellow and green highlights. He also wears a dark red-velvet trench and waist coat along with grey pinstripe pants, a green shirted bow tie, and fingerless gloves.

》Personality: In the original timeline, Maddox is a inquisitive and curious inventor and tutor. Maddox is also more grounded, thoughtful, and caring unlike his father.

When Red and Chloe alter the timeline, he witnesses them travelling back to the future and goes more insane than his father after nobody believed him.

》Friends: Red and Quren of Hearts and Chessy the cat.

》Family: He is the son of Mad Hatter and father of Max Hatter.

》Relationships: Red- Maddox acts as both Red's friend and tutor, he cares for her and often jokes around with her. After saving her from the Crimson Army, Maddox wishes for the Princess to have a good future and insists that as her friend and tutor, he insists she has one, going as far as to allow her to have the one she wants by using the Pocket Watch.

Queen of Hearts- Though Maddox innocently makes minor remarks of the Queen when speaking to Red, he still respects the former.

Chessy the cat- Maddox Hatter and Chessy the Cat is unstable and toxic rather than friendly or supportive.

Maddox is the main villain, driven by obsession—especially with control and time. As he becomes more isolated and mentally unstable, Chessy is one of the few characters who stays around him. However, she isn’t there out of loyalty or care.

Chessy thrives on chaos. Instead of helping Maddox, she manipulates him and often makes things worse. She enjoys the disorder around him and even encourages it at times. Their connection is built on shared chaos, not trust or friendship.

There’s also an imbalance in their dynamic. Maddox is unraveling and desperate for control, while Chessy remains unpredictable and playful in a darker way. She doesn’t take things seriously and could turn on him at any moment, simply because it amuses her.

Overall, their relationship isn’t healthy or stable. It’s more like an unstable villain paired with a chaotic instigator—working together, but never truly on the same side.

》Background/History: Maddox Hatter was born in Wonderland as the son of the Mad Hatter and an unknown mother. He also knew the young Princess Bridget, and two attended both Merlin Academy.

After the prank played on Bridget and her subsequent transformation into a villainous queen, Maddox refused to abandon her. Despite the dramatic change in her personality, he remained faithfully by her side for many years, offering her unwavering loyalty and support.

In time, Maddox became the father of a son named Max Hatter. He shared a loving and healthy relationship with his son, raising him with care and affection.

Following the birth of Red, Bridget's daughter, Maddox was appointed as her official guardian. Over the years, he developed a close bond with Red, serving not only as her mentor and protector but also as one of her most trusted friends.

Beyond the Isle of the Lost: Wonderland Maddox teaches a science class at Wonderland High, where Red is one of his students. He notices Red seems distracted and questions if she's okay. Maddox introduces a new student, Chester, to the class and asks Red to be Chester's lab partner. He ends the class after Red and Chester finish their work. Later, Maddox announces that there will be no homework that day, raising Red's suspicions. In another class session, Maddox teaches quantum physics. He asks Chester about his location during the quantum physics lesson, telling him that while his answer was perfect, it could have been more detailed. Maddox moves to the chalkboard to continue his lesson. He suggests that while a person can be invited to an "un-party," they wouldn't be able to attend without full information, such as knowing the time. When Red gives a perfect answer to a question, Maddox praises her for it. Red runs avoiding the Crimson Army until she is taken by the machinery of Maddox to his room, where he tells her that if she continues like this he won't always be able to save her. Red tells him what she can do while being imprisoned in Wonderland, and feeling like a lost cause, to which Maddox tells her that it is not like that, and that he worries about her future. After telling him that it's not easy having a controlling mother, Maddox tells her that the Queen wasn't always like this, and shows her his time machine: a Pocket Watch. But he warns her that changing the time structure can be dangerous, and sees that Red would have to use it when she was more mature, since he cares about her. After which, Red hugs him, thanking him, and upon hearing that the guards are still looking for the fugitive who was vandalizing the streets, Maddox sends her through a tube to her room, while he continues drinking tea.

In the morning, he alerts the Queen of Hearts of the arrival of a letter as a Royal Delivery. After reading that it is an invitation for Red to become a student at Auradon Prep, Maddox tells Red that she may have a future after all, traveling to Auradon and leaving Wonderland, but Red assumes that her mother will say no. However, the Queen accepts, much to Red and Maddox's surprise.

Current chronology- Maddox witnessed Red and Chloe's journey through time to the present and caught a glimpse of the Pocket Watch. For years, he tried to convince everyone of what he had seen, but no one believed him. Branded as insane, he eventually lost his sanity.

Over time, he began creating dangerous inventions to terrorize the kingdoms, becoming one of the most feared villains of his era. In the end, the Queen of Hearts had him captured and banished to the Isle of the Lost.

Descendants: Wicked Wonderland Maddox Hatter’s history has been dramatically changed by Red and Chloe using the Pocket-watch to travel back in time. After a teenage Maddox saw them use the watch to return to the present, he became obsessed with finding it and this eventually led to him terrorising the kingdom’s of Auradon and becoming a villain. The Queen of Hearts was forced to banish him to the Isle of the Lost because of this but once the barrier came down, she agreed to let him return to Wonderland as long as he gave up his search for the Pocket-watch.

When one of his inventions, the Oraculum, senses the Pocket-watch’s return he resumes his search and after being informed by Chessy that it’s in the royal vault he sends his mechanical Dodo birds out to find its location before capturing the Queen of Hearts and imprisoning her in her own castle.