- After having a horrible day, Bart gets a job tending bar for a group of gangsters and becomes the prime suspect when Principal Skinner mysteriously disappears.
- Bart is hired to work in a Mafia bar run by Fat Tony (making his first appearance). Bart is late for work due to having been put in detention by Principal Skinner. Fat Tony announces that he and his men will "meet and greet" Skinner, and shortly after that, Skinner disappears. Both Bart and Fat Tony are charged with Skinner's murder, and at the trial, Fat Tony tries to pin the murder (and all of his other illegal activities) on Bart.
- Bart wakes up thinking the day is going to be great, but a number of misfortunes befall him:
-Homer ends up claiming the 'genuine official police badge' in the cereal box -Santa's Little Helper eats his homework -He misses the bus to school and arrives late -His permission form to go to the chocolate factory is left at home
Bart ends up licking envelopes for Principal Skinner while the rest of the kids at school enjoy their time at the chocolate factory. On the way home from school, Bart is caught in the rain, and a wheel on his skateboard breaks, sending him down a stairway into the headquarters of mobster, Fat Tony.
On a whim, Fat Tony asks Bart to pick a horse to bet on for an upcoming race. Bart nonchalantly tells Tony to "eat my shorts." Tony assumes this is the name of a horse...only to reprimand Bart that the horse named "Eat My Shorts" is in a later race. Bart counters with "don't have a cow," and (amazingly enough), this is the name of a horse in the race Tony is betting on. All the horses in the race appear to have names that are cartoon character catchphrases (such as "Yabba-Dabba-Doo" and "I-Yam-What-I-Yam"), and the horse named "Don't have a cow" wins, much to Tony's delight.
Tony also has Bart attempt to mix drinks, with Bart's preparation of a Manhatten considered "su-poyb" by one of Tony's men. Tony soon decides to hire Bart and pays him well. Bart goes out of his way to tell his family that he has a part-time job, but doesn't reveal just who or what he's working for.
Bart's association with Tony soon leads to him hiding a truckload of stolen cigarettes in his room, with Tony and his men giving Bart a new suit as a gift for holding onto the cigarettes.
Eventually, Marge grows more concerned about what Bart is doing, and asks Homer to meet with Bart's boss. Homer ends up playing a game of poker with Fat Tony, in which Tony and his men allow Homer to win to keep Bart in their employ. Homer is convinced that Tony and his men are okay, and relays this to Marge.
At school soon after, Bart pays several of his friends to spray graffiti about Principal Skinner on the school building. When Skinner catches them, Bart attempts to bribe Skinner to keep quiet. This leads to Bart being held in detention, keeping him from serving one of Fat Tony's acquaintances who just happened to come on the promise of Bart's preparation of Manhattens.
Bart eventually shows up late. When Tony chastises Bart, Bart angrily explains how Principal Skinner held him after school. Tony decides that he and his boys will go to "meet and greet" Skinner.
The next day, Skinner goes missing, and a almost all of Springfield is searched. A psychic is even brought in to possibly find Skinner, but her skills do not reveal anything. Bart's guilt that he may have caused Tony to murder Skinner eventually causes him to have a nightmare, and he quickly rushes to see Tony. Tony's henchman claims they didn't kill Skinner, just when Chief Wiggum shows up, arresting everyone in the room for Skinner's murder.
Bart is put on trial, with the possibility of receiving 180 years on the charge of "murder one." On the stand, Fat Tony and his men all claim they were innocent bystanders, and that Bart was the head of the crime syndicate. Naturally, Bart is upset at seeming to be betrayed by his employer.
Almost all the testimony seems to point to Bart, but just as he is about to be sentenced, Principal Skinner bursts through the court room door!
Skinner explains that Tony and his men met with him to simply have a few words, but Skinner soon ordered them to leave (a request that Tony complied with). Skinner then went home to bundle old newspapers, but ended up being trapped under the enormous pile when it fell on him. Eventually, Skinner used scientific know-how to get out and survive.
The charges against Bart are dropped, but Bart is still upset over what Tony and his men said, blaming him. Bart cuts ties with Fat Tony, but the ordeal soon spawns a made for TV movie, titled "Blood on the Blackboard: The Bart Simpson Story," with Neal Patrick Harris playing Bart. However, since the producers changed the story and events, the family sees no royalties from the movie.
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