Madison was a classmate of Cory Baxter's and the best friend of Cory's season 3 girlfriend Cindy. She considered Cory a "big dummy."
Madison was originally one of the "cool girls" that Cory wanted to hang with, but was denied access because his best friend William was too nerdy. Cory tried to change William but nothing seemed to work. With some advice from his mom, he eventually realized that William was okay the way he was and decided not to join the cool group.