Penny Madrid is a supporting antagonist of the Fillmore! episode "Immune to All But Justice". She was the former secretary of Winston Kotter and a former friend of Cornelius Fillmore.
She was voiced by Francesca Marie Smith.
Penny was known to be former delinquent who aided Fillmore in his rebellious activities during their early days in X Middle School. Eventually, they parted ways as Fillmore became a new Safety Patrol Inspector while Penny becomes a new secretary to Kotter (the son of the Canadian ambassador).
During the school's Canada Cares celebration, Penny was first seen meeting Fillmore (who was on guard duty) until the Safety Patrol were chasing down Jack Staples, who was caught smuggling something through the cafeteria. Just as the Patrol was about to take Staples into custody, Penny pointed out that Staples is actually Kotter's bodyguard, and Kotter used his diplomatic immunity to vouch for Staples. Eventually, O'Farrell learned that Staples was smuggling counterfeit baseball cards and printing ink that were in Kotter's possession, prompting Fillmore and Third to head over to confront Kotter for his actions before leaving.
Deciding to take things up a notch, Kotter sends in Staples and several thugs posing as hockey players to attack Fillmore and Penny Madrid (who is Kotter's secretary) when they found more of the counterfeit stash. Fortunately, Fillmore and Penny escaped, and the former confronted Winston at the Canadian consulate before leaving. Unperturbed, Winston continues on with his plan by sending Staples to purchase several plates to print out the fake baseball cards. He then spotted Penny calling Fillmore, prompting him to take Penny prisoner in the school's natatorium. As Kotter gets his thugs to produce the baseball cards using a printing press inside the pool, he plans on pinning the blame on Penny to cover his tracks.
However, this was not the case when Fillmore and Third arrived to the rescue by bringing in the entire Safety Patrol to shut down the operation and put Kotter and his thugs into custody. That afternoon, Penny shared a dinner with Fillmore at her house, where she accidentally blurted out a baseball player's name while mentioning how impossible for 4,000 cards to disappear. This made Fillmore suspect something as no one said anything about the player, and found out that Penny has her own stash of counterfeit baseball cards in her garage. Realizing that Penny was just using him to shut down Kotter's operation in order to sell the cards herself for profit, Fillmore confronted Penny for this. She tearfully admitted that it was complicated for her to do so, but admitted that she still had feelings for Fillmore. However, Fillmore refuses to accept this and left, demanding that Penny turn herself in first thing in the morning or she would be tracked down.
Knowing that Fillmore is not bluffing, Penny presumably surrenders herself to the Safety Patrol for her villainous actions.
- Penny is obviously a parody of the character Rika van den Haas from Lethal Weapon 2, as they both are secretaries of corrupt foreign diplomats who were being used by their bosses. However, unlike Rika, Penny is a little more villainous as she wanted to exploit Kotter's downfall to enrich herself.