|“||You're cold, vicious, and heartless, you're the big sister I've always wanted.||”|
— Madeline to Jessie
Madeline was at a MENSA meeting in Central Park, where Ravi was with Jessie looking for a new friend. Madeline was among the first to approach Ravi and Jessie would tell Madeline to please accept him as a friend since he has none. While she gets to know Ravi, Jessie spends time with another MENSA partner named Scott.
Then Madeline would come to the penthouse with her new friend as they would share their common interests with each other. However, Zuri comes by and meets the spectacled little girl and successfully convinces her to watch Power Ponies together, stealing Madeline away from Ravi, only to make him jealous.
After awhile, she comes back and spends time with Ravi again. Ravi would quiz Madeline on a very complicated math question, to which she would solve it in less than a second. Then Emma comes down the stairs and introduces herself to Madeline. But in this encounter, a ring and Emma's necklace catches her eye, Madeline commenting on what a nice necklace she is wearing. Emma then tells Madeline to come upstairs with her and show her her other collections of jewelry she finds precious. Once Madeline was alone, she removed her glasses and told an "anonymous" person through her cellphone the nanny has left the building and it is only the children and her so she tells this mysterious stranger to come down, revealing herself to be a thief.
Night fallen, Madeline witness' Ravi getting very upset with Zuri and Emma and comes up with a "therapy" by handcuffing all three kids so they calm down and don't fight. But this is all a trick as Madeline removes her glasses and this time her bun as Emma wonders if this is part of the therapy. Madeline tells Emma she is simply robbing them but she still doesn't get it.
And just as Jessie arrives (and later, Luke and Bertram), Madeline also reveals to her she is a thief and Scott joins her, as she kicks Jessie in the shin before cuffing her. Madeline then heads upstairs to steal more jewelry along with Scott before coming back and seeing Jessie and the kids attempt to escape. But Jessie appeases with her and Scott to join their team, which convinces Madeline to uncuff her and join their burglary team. But little did Madeline know, it was part of a trick for her brother Scott, due to his arachnophobia, saw a box with spiders inside and trapped Madeline behind his back, pushing her against the wall.
The cops arrive and Madeline and Scott are arrested for their crimes. Ravi, though, questions if he can still be able to communicate with her, though Madeline tells Ravi it is very unlikely.
- Madeline is a fan of Power Ponies (a portmanteau on Power Rangers and My Little Pony).
- She is very brilliant at math, as shown when she is quizzed by Ravi on a very complicated question, or she could've faked it by looking down at the answer sneakily.
- Her Mom is a thief as mentioned by Madeline when she told Scott she and their mom were gonna pull of a crime in Vegas without him.