The villainous Lindsey Naegle
Lindsey Naegle (Tress MacNeille) was a recurring character on The Simpsons, appearing throughout the series as a local businesswoman in Springfield. However, in "Uncut Femmes", episode 32.17 (airdate March 28, 2021), she was revealed as a villainess.
Lindsey's backstory in the episode revealed that she had been a criminal alias of" Red" in her youth, teaming up with fellow thiefs Sarah, Erin and Bette to rob the priceless Hourglass Diamond from a penthouse. While Sarah was distracted after meeting the night security guard Clancy Wiggum (who she eventually married), the other three woman were able to extract the diamond from it's safe. At that moment, Lindsey revealed her villainous colours, tripping the burglar alarm and slipping away with the diamond while Bette and Erin were arrested. After escaping, the evil Lindsey used the money they had made to fund herself a life a luxury, while also keeping the Hourglass Diamond in a tiara.
The episode's plot saw Bette and Erin recruit Sarah and Marge Simpson into a plan to finally take their revenge on Lindsey. The plot involved stealing back the diamond at the annual Gen Gala, which Lindsey would be attending as the date of actor Rainer Wolfcastle, and replacing it with a fake. At the gala, Marge went undercover as a guest and distracted Lindsey with a conversation, allowing Sarah to make the switch. After ordering Marge to leave, Lindsey realised what had happened when the fake diamond fell out of the tiara and shattered on the floor.
The villainess then sent the event's security guards after Marge and Sarah, whose own husbands unintentionally foiled their escape. As Lindsey marched towards Sarah, Marge tripped her with the trail of another guest's dress, causing the villainess to fall down the stairs of the Gala venue and land in a crumpled heap. Rainer then arrived and revealed he'd found a new girlfriend and was dumping her. As Lindsey got to her feet, Erin and Bette (disguised as event staff), handed her her purse, which was filled with items they had stolen from other guests. Lindsey was last seen being arrested for the thefts she had been framed for.