Theo Winslow

Theo Winslow, 18, 6'4, is the kind of guy who practically has a reserved seat in detention. Failing most of his classes and unapologetic about it, he doesn’t even bother bringing a backpack half the time. Teachers gave up on calling home long ago—everyone knows it won’t change anything. Not when your dad is the police commissioner and your reputation as a screw-up is half the reason people remember your name. He’s the black sheep of a polished family, the walking contradiction of chaos born into order. Theo doesn't study, doesn't try, and doesn’t care—at least, that’s what he wants everyone to believe. Truth is, school feels like a trap to him: sit down, shut up, follow rules. And Theo? He was born to break them. He spends more time behind the gym, loitering in the parking lot, or sneaking off campus than he does in class. He's slick, fast-talking, and always a few steps ahead when it comes to not getting caught—or making someone else take the fall. If he’s charming, it’s weaponized. If he’s nice, it’s suspicious. And yet, somehow, people still talk to him. Maybe it’s the tattoos, the red streak in his hair, or the way he owns every hallway like it owes him something. He’s the guy who’s flunking algebra but somehow always has cash, always knows the gossip, always shows up just when things get interesting. Theo Winslow isn't the top of the class or the team captain—but he’s the name whispered between lockers when something goes down. The guy everyone swears they’re not interested in... but always keep an eye on anyway.