Wendy Pleakley is a major character in the Lilo & Stitch franchise. A former member of the Galactic Federation, Pleakley reluctantly became Jumba Jookiba's partner when forced to assist him in capturing the escaped Experiment 626. With his friend's servitude with the Villain League being canon, Pleakley would be considered to be a Villain League member to an extent. However, he's not really a villain leaguer, due to Jumba not really a member, rather, a hired scientist.
Lilo and Stitch
In the movie he was called upon to assist mad scientist Dr. Jumba Jookiba in tracking down Experiment 626, which had escaped to the planet Earth. He and Jumba were both fired and sentenced to a prison term by the Grand Councilwoman of the planet Turo, for failing to capture Experiment 626. In the subsequent television series, Pleakley and Jumba have remained behind on Earth and has become a member of Lilo's ʻohana, or extended family.
Lilo and Stitch 2: Stitch has a Glitch
In the film, Pleakley assists Jumba as they try to find the solution to Stitch's Glitch.
Stitch! the Movie
Pleakley appears in the film trying to free Jumba from Gantu and Hamsterviel.
Leroy and Stitch
Ultimately as a reward for his help in capturing and taming Jumba's expirements he is granted a position at Galactic Alliance Community College as Head of Earth Studies. He gets an assistant (who is excited to learn he is actually been to Earth), a new wardrobe, and the keys to the college's car pool van but is only a supervising professor and is dissatisfied with not being able to spread his knowledge of Earth and starts to miss Jumba and the rest of Lilo's family. He goes to visit Jumba in the GACC van but gets caught by Hamsterviel and nearly sent into a black hole which Stitch manages to save him, Pleakly and Jumba from. He returns to Earth for the battle with Leroy and his clones and operates the lights during Lilo and Stitch's impromptu Aloha Oe concert (accidentally blinding himself at first). He later quits his job at Galactic Alliance Community College and returns to Earth to be part of Lilo's family once again.
Lilo and Stitch: The Series
In the television series, he had a brief mock engagement with Nani to placate his pushy visiting mother. In this same episode he also had a mock engagement to Jumba. Pleakley's mother is concerned that he has not found "the right girl" and that he is not married. Pleakley feels he must pretend to be married for his mother to approve and accept him. When his family arrives on Earth for the mock wedding of Nani and Pleakley, he reveals that he is happy being who he is, which includes being unmarried. After that his family becomes more understanding of him and loves him for who he is. Gantu fell in love with him (under the influence of one of Stitch's cousins), mistaking him for a girl. An entire room full of people fell in love with him because of the experiment at the Valentine's Dance, however Lilo's friend (and crush) Keoni was the only one to have a real crush on him (which did not last long).
Role in the series
Pleakley reprises his role from the film, but is now being watched over by Cella because she felt him to be incompetent. Cella now works with Pleakley to watch over Lilo and Stitch's family, though later SAF appearences in Chronicle Episodes shows that she rotines between that and doing Galactic Federation work.