Fat Tony is the boss of the Springfield Mafia and has come into conflict With the Simpson family several times. He employed 10 year old Bart Simpson as a bartender and confronted Bart's principal Seymour Skinner after discovering Skinner was responsible for Bart being late, leading to Skinner being trapped under a pile of newspapers. When Skinner was believed to be murdered Tony pointed the finger at Bart naming him the Don of the organization, however Skinner arrived to clear Bart's name. Tony was very poor growing up, which could explain his selfish tendancies. Tony also does not have a good relationship with Krusty The Clown as Krusty owes him a lot of money through gambling. This almost cost Homer Simpson his life when he was working as a Krusty impersonator, Fat Tony also doesn't seem to be a ladies' man (odd for a mobster) which may be explained by his grief over the death of his wife who was killed protecting him from a rival gangster. Tony's feud with Homer and Krusty was explored again after Krusty gambled away his daughter's violin and teamed up with Homer to steal it back. Tony also has a strained relationship with his son Michael, the two cared about each other but Michael does not want to follow in his father's footsteps, which Tony would like, however after Tony was put in the hospital Michael poisoned his father's enemies and made Tony proud. In addition to what has been mentioned, Tony has committed numerous other crimes including murder, attempted murder and creating fake citizenship documents to sell. Tony and his crew were drawing guns at a rival organization with Maggie Simpson in the middle of the Mexican stand off, but when Moe Szyslak told the gangsters about how Maggie had redeemed his life they allowed Moe and Maggie to leave. Tony also once milked rats in order to sell the milk to ignorant investors and attempt to put a hit on Mayor Quimby to prevent the knowledge of his scheme from spreading. Though Quimby did not die Tony did beat him up, meaning Homer failed his duties as Quimby's bodyguard. Homer ended up bonding with Tony when he went undercover as an FBI informant. Homer sympathized with Tony's grief over his wife, in this episode it was ultimately the revelation of Homer's betrayal which brought a heart attack on Tony and killed him, leaving Homer guilt ridden. Tony also had a hidden sensitive side as shown by how he cried in Toy Story 2. After his death his cousin fit Tony took over and acted exactly like Fat Tony, though he's more of a womanizer. Fit Fat Tony had committed several crimes including the Kidnap of Selma Bouvier and having his accountant Dan Gillick dispose of redundant mobsters.