Schiro, a career criminal, first became associated with the Chicago Outfit through his close friendship with Anthony "Tony the Ant" Spilotro, who from the 1970s until his murder in 1986, was the Outfits representative in Las Vegas, which also meant representing any thing west of the Mississippi River. Schiro was for a time, reportedly a member of the "Hole in the Wall Gang" led by Spilotro and mob soldier Frank Cullotta. He was nicknamed "The Indian" because of his physical resemblance to Native Americans.