Maddox is the son of the Mad Hatter, the father of Max Hatter and Ally, and the husband of Alice Hatter. In the altered timeline created by Red and Chloe, Maddox is now known as the greatest and most evil villain in all of Auradon. In the original timeline, he was a quirky but sane inventor and the kind tutor of Red. When Red and Chloe changed the past and the Queen of Hearts, it changed reality, and Maddox was turned bad and sent to the Isle. He’s finally been allowed back to Wonderland, home. He’s taking it to his advantage and wants his pocket time-travel watch back. He has gone completely mad from his time on the Isle and is obsessed with his pocket watch and his evil plans, neglecting to give his son Max emotional support. However, he is entirely devoted to Alice. He is a terrifying, chaotic force to the rest of the world, but turns into a sweet, obedient partner the moment Alice speaks. An example of this happens when Maddox is trying to give his son dating advice. When Max starts seeing Chloe, Maddox tells him to talk to her and "be a man." Max replies, "I’m a man." Maddox quickly adds, "Defend yourself!" Right then, Alice arrives and tells him, "Come now, we’re gonna be late." Maddox instantly drops his tough villain act and says in the most humble, sweetest tone possible, "Be right there, sweetheart." Once Alice walks away, Maddox turns back to Max and tells him, "It’s a totally different situation." Maddox is an Asian man with dark brown eyes and light skin. He wears a plaid top hat and has shoulder-lenght wavy purple hair with 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 with black-painted nails. Maddox invented the pocket watch. Though he warned Red about the consequences and tried to take it back (before she stole it during a hug), he anticipated that time could be messed up. He enchanted the watch so that Alice would retain her memories.

Character from Descendants Age: 16–17 Gender: Male Faction: Wonderland Student Parentage: Maddox Hatter, Alice Hatter Sister: Ally Appearance: Asian. Light skin. Black hair with purple streaks, slightly messy but intentionally styled. Lean build. Black and purple color combination. Small black hat. Energetic physical presence. Smokey eyeliner Backstory: Grew up entirely in the rewritten timeline where Wonderland has always been integrated into Auradon’s world. Was sent to the Isle of the Lost with his father at 8 years-old where he learned how to pickpocket. Personality: Cynical, innovative, intelligent, fiercely loyal, sassy, playful and competitive with his friends, enjoys showing off hat tricks, observant on people’s emotions (from Alice), socially direct. Comfortable with Wonderland’s unpredictable logic. Was a HK (Hero Kid) in the original timeline before Red and Chloe changed his life. Originally was a sweet-natured, if awkward, young man. Relationships: Parents - insisted that he and his father were nothing alike, despite Felix joking, "Well, you are related," when Max complained about their twisted plan. the one positive thing in his family life is that his parents are sickeningly, endlessly, absurdly in love. while every other Isle villain has a toxic marriage, messy divorce, or absent partner, Maddox and Alice are thriving. Red of Hearts – he learns of what she’s done and becomes furious with Red for throwing his life away, calling her out on a "pretend persona" as a perfect princess and "heartless". Wonderland peers – integrated naturally VKs - friends with his VK gang: Hazel Hook, Felix Facilier, Squeaky and Squirmy Smee Chloe - has a crush on her but is shy about it, understands her situation

Ally bears a strong resemblance to her mother, has long blonde hair, blue eyes, heavy eyeliner, and adores flowers. She becomes clumsy-evil in the altered timeline but is sweet with her family.