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Penny Madrid
Penny Madrid is an X Middle School student.

Penny used to be a troublemaker like Fillmore used to be, often known for dangling students upside-down to steal falling loose pocket change. Like Fillmore, she has since reformed, and currently serves as an assistant to Winston Kotter.

After she and Fillmore meet up again, they did a little catching up with each other[1]. She helps out Fillmore when it was discovered that Winston is running a counterfeit baseball card ring. After the case is thought to be closed, many of the cards are still missing until Penny slips up and accidentally reveals that she was the one who took the cards. She intended to get Winston blamed and then start the ring herself, taking all the profit. Fillmore allows Penny the chance to turn herself in, otherwise he would bring her in himself. 

It is implied that Penny has feelings for Fillmore, and though Fillmore is shown to have a slight crush, it is quickly put to rest when he discovers Penny's deceit. 

References

  1. Immune to All But Justice

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