The first time Tony Oppedisano met Frank Sinatra (a connection facilitated by Sinatra’s confidante Jilly Rizzo at his namesake Manhattan club), the two immediately hit it off. Despite being decades younger than the superstar, Tony, then a fledgling singer, and Sinatra formed a close bond which stretched from the 1970s to the night of May 14, 1998, when Tony was in the hospital room, along with Frank’s wife Barbara, when he passed away. In the intervening time, Tony O became one of Sinatra’s best friends and closest consiglieri; a drinking and smoking buddy Sinatra could lend an ear to, a confidante to help him out or just a guy to goof around with.