Penny Madrid
Penny Madrid is a student in X Middle School. She is a former delinquent who, like Fillmore, has since reformed and works under the Canadian ambassador Winston Kotter.

Penny and Fillmore reunited during one of Winston’s charity events[1]. After a suspicious incident involving Winston’s bodyguard, Fillmore asks Penny about her knowledge of Winston’s activities. Penny tells him that Winston is a charitable person who works for the school’s benefit. She reminds Fillmore of how they used to work together as delinquents until their respective parties changed their lives for the better (Winston Kotter for Penny; Safety Patrol for Fillmore).

Penny accompanies Fillmore as he searched for Winston’s connection to a counterfeit baseball card ring. After Fillmore shows her paper hidden in a crate of candy and Lumberjack ambushes them, Penny becomes convinced of Winston’s criminal activity. Fillmore and Ingrid ask her to gather information regarding the counterfeit card ring.

Penny first calls Fillmore to tell him that Winston ordered printing plates and provides the location of the pick up. When Fillmore and Ingrid fail to follow the plates to the printing site, Fillmore tells Penny to be careful from that point on. Penny assures him that she will be fine. 

However, Winston catches her calling Fillmore about the location of the printing site. He takes Penny to an old pool building intending to frame her for the counterfeiting. Fillmore and Ingrid arrived with the rest of the force to shut Winston’s business down.

After the case is thought to be closed, Fillmore notices that many of the cards are missing from Winston’s inventory. Fillmore discusses this problem to Penny over dinner. She tells him to not worry about it, but accidentally mentions the player and the team of the missing cards. Fillmore realizes she intended to get Winston dispatched 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.


  1. Immune to All But Justice