According to pornography gossip columnist Luke Ford, Gallo was one of the biggest cocaine smugglers and gangsters in the Los Angeles area in the late 1980s and early 1990s. Gallo eventually became connected with the Los Angeles crime family under Vincent "Jimmy" Caci, with whom he was arrested in 1998 by the FBI in connection with the Las Vegas RICO cases "Operation Thin Crust" and "Operation Button Down." In the early 2000s, Gallo moved to New York City and worked with the Colombo crime family under soldier Edward Garaofalo and eventually caporegime Theodore Persico, Jr. In 2004, court documents from the prosecution of Teddy Persico show that Gallo, a paid government informant, frequently wore a wire and recorded conversations with Persico. Gallo has also claimed responsibility for the arrest of Lucchese crime family capo John Baudanza and Colombo soldier Craig Marino. While he went into the federal witness protection program, Gallo has published personal photos from his time spent with Mafia associates on Jerry Capeci's This Week in Gangland column and on his personal blog.
Following the death of convicted hitman Charles Harrelson, Gallo was interviewed and identified in the Sunday 2007 issue of The Sunday Times as a "convicted Mafia associate" and friend of Harrelson.
An adult film and B-movie director and producer from the late 1980s to the early 2000s, he directed about 29 pornographic films. He was also the producer of the B movies Babewatch 3 and Babewatch 4. While a filmmaker, Gallo met and married adult entertainment star Tabitha Stevens; their short-lived marriage included a Jerry Springer Show episode titled "I'm Married to a Porn Star!" They divorced in 1997.