Principal Prickly gets his wish of finally being a middle school principal; however, his replacements, an evil man named Dr. Slicer and his assistant Gilda, are even worse. This causes celebrations to be cut short.
During one of the day's recesses, Prickly gets a call: Superintendent Skinner has a middle school principal position open at Spiro T. Agnew as the previous principal was "fired." Prickly has an open application for positions such like this and hence is offered the job; Prickly is overjoyed - but not as much as the students who welcome a break from him. However, Miss Finster is not happy, for she and Prickly have been best friends for decades.
After discussing their plans on what they'd do after Prickly left, Menlo - who was with Miss Lemon and Prickly outside his office - responded to the gang. He was not initially phased - until he read a fax that had come in, however. That's because it read that Prickly's replacement is an even worse man known only as "Slicer."
Slicer and his assistant Gilda visit, instantly he sorts the schools "problems" and encourages more Discipline. While T.J. initially tries to butter up to the new Principal, Slicer dismisses Detweilers attempts at niceties; intimidates him; orders him to remove his hat and gives him a humiliating paper hat to wear.
After Slicer's visit, T.J. decides that he and his gang must do everything they can to stop him becoming Principal. The gang realizes the only way to retain Prickly is to incentivize him to not leaving. Attempt one involved them broadcasting a fake news broadcast in Prickly's office to portray the school as dangerous, but Prickly immediately dismisses the credibility.
Finster, however, organizes a school-wide goodbye celebration. While Skinner is impressed with the exposition, the gang's next attempt to derail Prickly's promotion to Middle School is to portray themselves as Middle school students with all the subsequent problems a principal may have to deal with. However their plan fails once again; finally T.J. gives a heartwarming speech to Prickly just before he leaves. Prickly is touched, but Slicer is not amused, and he makes T.J. wear a paper hat that says "Capt. Sappy" (earlier Slicer made T.J. wear a hat that said "Funny Boy".)
Dr. Slicer immediately appoints his assistant, Gilda, to Miss Finster's position, making her Gilda's assistant. He also plans to tear down the jungle gym to make room for a guard tower and that he was to restore the cannon in the front of the school operational.
The next day, everyone prepares for Slicer while T.J. panics over which hat Slicer wanted him to wear. However, Prickly returns and Slicer is heard protesting but Prickly dismisses him. Prickly claims that the Superintendent wouldn't "cough up" enough money for the position at Spiro T. Agnew, and decides to stay at Third Street until "they make a better offer". But the final shot, in which Prickly smiles as the kids cheer at his decision to stay, gives plenty of implications for the real reason why he didn't accept the job as middle school principal.
- Coloring error: Just before Slicer arrives the next day, Butch's eyes turn green in the background for a brief scene.
- Animation error: When Spinelli is dressed in a dress to act like a middle school girl, the long-distance shots did not reveal her stomach, however, the short-distance ones do.
- In one scene, the gang tries to stop Prickly from leaving by presenting him with their best impressions of middle school problems (which are humorous but in a few cases, staggeringly accurate). They are as follows:
- T.J. replaces his jacket and hat with a red plaid shirt and a blue beanie respectively. He supposedly acts as an oppressed and disrespectful student as he yells at the Superintendent after the latter asks him why he did not line up with the rest of the students ("That's because I reject you, man! You and everything you stand for!").
- Gretchen acts like the stereotypical goth, complete with a totally different appearance, no glasses, black lipstick, red dyed hair (possibly a wig, as her hair is once again brown afterwards), black shirt and choker, chain necklace, and teal pants and portraying a nihilistic outlook on life.
- Vince wears a gray shirt with ripped off sleeves, red shorts with a black line down the sides, and no neckbands. It is possible by his demonstration that he is supposed to be a disturbed jock suffering with an eating disorder ("I know I gotta make weight, but I can't live on ginseng and egg whites forever!").
- Mikey has (possibly) fake pimples all over his face, making it look like he's breaking out.
- Gus just says he has father issues.
- Spinelli's hair looks like it's blown back (similar to Hector's hairstyle) with a brown hairband in it. She also has a teal striped tank top, an orange skirt, blue stockings, and brown shoes. Her demonstration was to pretend to hit on Prickly with a magazine clutched over her chest, creeping him out especially.
- Slicer bears a resemblance to Heinrich Himmler.
- Early in the episode, when it was announced that Prickly would be leaving Third Street, T.J. stated he had a plan for the Ashleys - involving electromagnets. Further on in the episode, when T.J. first greeted Slicer by referring to him as "slicey baby," Slicer responded by calling T.J. a "funny boy." Moreover, that he didn't like funny boys as a funny boy gave him a scar on his left cheek (in the shape of an inverted number '3') that was caused by electromagnets.
- This episode marks Julie Ann Sipos' first and only credit as a writer. She has worked as both a producer and an actress for other programs.
- This is the second and last episode where Spinelli is shown with red lipstick on; the first being "The Beauty Contest".
- This is one of the only episodes where Spinelli is seen having at least one eyelash; the others being "First Name Ashley" and "Mama's Girl". However, this episode and "First Name Ashley" are the only episodes where it had Spinelli to have two eyelashes on each eye, as "Mama's Girl" had her to have only one eyelash on one of her eyes briefly during her eye zoom (though, this is an animation error).
- T.J. Detweiler - Andrew Lawrence
- Vince LaSalle - Rickey D'Shon Collins
- Ashley Spinelli - Pamela Segall-Adlon
- Gretchen Grundler - Ashley Johnson
- Mikey Blumberg - Jason Davis
- Gus Griswald - Courtland Mead
- Miss Finster/Gilda - April Winchell
- Principal Prickly - Dabney Coleman
- Randall Weems - Ryan O'Donohue
- Menlo - Blake Ewing
- Superintendent Skinner - John Astin
- Dr. Slicer - Tim Curry
- Haiku Generator Game Voice - Gregg Berger