In the early 1970s, Vitabile was a soldier in the crew of Giovanni Riggi. In 1976, family boss Sam DeCavalcante retired to Florida and Riggi succeeded him as boss. Riggi then designated Vitabile as his consigliere and Girolamo Palermo as underboss. The DeCavalcante family would be under this steady leadership for the next fifteen years. However, the late 1980s brought law enforcement investigations that would shake up the family throughout the 1990s.
In July 1990, Riggi was convicted of racketeering and conspiracy and sentenced to prison for 15 years. Still in charge of the family, Riggi named Gaetano Vastola as his acting boss and Vitabile remained as consigliere. However, in 1991, Vastola was convicted of extortion and went to prison. DeCalvalcante replaced Vastola with John D'Amato
In November 1991, Vitabile was involved in the murder of Louis LaRasso, the longtime underboss of the DeCavalcante family. John D'Amato was angry at LaRusso due to a disagreement and ordered his murder. Mobster Anthony Capo and two associates shot LaRasso. The body was never recovered.
In 1992, Vitabile ordered the murder of acting boss John D'Amato due to D'Amato's alleged bisexuality. D'Amato girlfriend had reported to Capo that D'Amato frequented sex clubs and was having relations with men. When informed of this, Vitabile ordered D'Amato's execution. Since Cosa Nostra rule forbade the killing of a boss without permission of the Mafia Commission, and D'Amato was friends with Gambino crime family boss John Gotti, Vitabile had to act secretly. Capo and a mob associate picked up D'Amato at the girlfriend's house in Brooklyn and shot D'Amato in the car. The body was never recovered.
After D'Amato's death, Giovanni Riggi appointed Giacomo Amari as acting boss. However, in 1995 Amari became disabled due to stomach cancer and could no longer run the family. With Riggi's approval, Vitabile re-structured the family leadership to have three caporegimes on a Ruling Panel to make the day-to-day decisions on the family. These capos were Vincent Palermo, Charles "Big Ears" Majuri, and Girolamo Palermo. Vitabile remained as consigliere.
In 2000, Vitabile reportedly became acting boss, running the family along with Joseph Miranda and Vincent Palermo. Later in 2000, Palermo became a government witness and testified against Vitabile. In June 2003, based on testimony from Palermo and government witness Anthony Capo, Vitabile was convicted of a sweeping racketeering conspiracy that included the LaRussa and D'Amato murders, extortion and stock fraud. In June 2006, Vitabile was sentenced to life in prison.
In September 2008, Vitabile's racketeering conviction was overturned by a federal appeals panel, which ordered a new trial. The government promised to appeal the decision but as of June 2010, Stefano Vitabile was being held at the FCI Allenwood, PA. He was released on November 22nd, 2013. His current position in the family is unknown.