|“||I'm gonna whack ya in the labonza!||„|
|~ Legs threatening someone.|
Along with Louie, Legs is Fat Tony's bodyguard and personal assassin. He is also a "mob doctor", with years of experience in surgery from treating bullet and stab wounds. He rarely speaks, but when does it is usually to defend his boss or argue with other low-level mobsters.
When Fat Tony is killed by rival mobsters, Legs becomes a right-hand man to his cousin and successor, Fit Tony.
Legs first appears in "Bart the Murderer", the episode that also introduces Fat Tony and the rest of the Springfield Mafia. He accompanies Fat Tony to threaten Principal Seymour Skinner on behalf of Bart Simpson, their new bartender at the "Legitimate Businessman's Dinner Club". Nevertheless, he and the others leave when Skinner orders them out. When Skinner disappears, he, Fat Tony, and Louie are accused of killing him. When Skinner re-emerges, alive and well, Legs and the other mobsters are released.
In "Homie the Clown", Legs and Louie kidnap Homer Simpson, believing he is Krusty the Clown, who owes them money. They bring Homer before the head of the Springfield Mafia, Don Vittorio D'Maggio, and watches as Homer and Krusty perform the Loop-de-Loop Trick. During this episode, when Homer claims to be Barney Gumbel to save his own skin, Legs angrily retorts, "The same Barney Gumbel who's been taking pictures of my sister?"
While he is usually depicted as thuggish and dim-witted, this episode shows Legs to be knowledgeable about American history; When Homer panics and claims to be Benedict Arnold, Legs replies, "The same Benedict Arnold who surrendered West Point to the hated British?"
In "Mayored to the Mob", Louie tells Homer that the late Joseph Kennedy gave him his nickname, although he does not elaborate on why Kennedy gave him the moniker.
In "Moe Baby Blues", Legs joins the rest of the Springfield Mafia in a "Mexican-Italian-American Standoff" with the Castellaneta Family (a reference to The Simpsons cast member Dan Castelleneta) at Luigi's Restaurant. Maggie Simpson is nearly killed during this conflict, but Moe Syszlak saves her at the last minute by testifying to her sweetness and innocence, moving the mobsters to stop fighting and forgive each other; Legs in particular collapses, weeping, into his opponent's arms.
In "The Seven-Beer Snitch", he and Louie try to kill Homer after he informs on them to the police.
Legs appears in the mobile game The Simpsons: Tapped Out, in which he and the other mobsters once again hire Bart as a bartender. In the game, Legs mentions that he has a night school Master's degree in Fiscal Studies.