|Occupation||Former crime boss; Chef|
|Relatives||Spouse: Lisa Simpson|
Children: Tony Jr., Johnny, Emelia
|First Appearance||The Mook, the Chef, the Wife, and Her Homer|
Michael is the nephew and heir apparent of the D'Amico crime family underboss Fat Tony (originally known as Fit Tony), and the son of the late ex-underboss Anthony 'Fat Tony' D'Amico. When Don Vittorio DiMaggio passes away, Fat Tony becomes the new Don and he promotes a reluctant Michael as the new underboss. However, Michael still does not wish to follow in the footsteps of his late father and his uncle. When he rekindles his friendship with Lisa Simpson and falls in love with her, he starts to carry out his dream of legitimizing the family business.
Relationship with Lisa Simpson
He was first friends with Lisa when they were both students at Springfield Elementary School. They became friends when she sat beside him in the school cafeteria while all other students turned away from him due to his reputation as a crime boss's son. After the rivals from the Calabrese crime family attacked his father, Lisa's father and brother took over as acting underbosses for the family businesses. Seeing as his new friend's family were getting dragged into the life of organized crime, Michael conducted a plan and invited the Calabreses to dinner, where he poisoned them - hence, eliminating his father's enemies and relieving Homer and Bart from their duties. He also had to break off his friendship with Lisa because he could not bring himself to tell her that he had intentionally poisoned the Calabreses.
Several years after he returns home from Princeton University, he meets Lisa again by chance at a coffeehouse, and they rekindle their friendship. However, Michael finds himself falling deeply in love with her as they start to see more of each other. He eventually confesses to Lisa about everything about his past life, including the family business, the assassination of the Calabrese rivals, and his past abusive relationships with other women. As he had greatly feared, Lisa initially distances herself away from Michael until she later realizes that she still loves him underneath it all, and does not care about his past.
Relationship with Felicia Brooks
Marriage and Family
Eventually, he and Lisa get married in Sicily where they settle down and have three children, Anthony Jr. (who is named after his grandfather), Jonathan (named after Johnny Tightlips, one of the Family's most trusted caporegimes), and Emelia, and they live happily ever after.