Gambino, Genovese and Lucchese fought an on-and-off war with Joseph Bonnano, the head of the Bonnano crime family. Bonnano steadily lost ground as he lost allies: Albert Anastasia was murdered in 1957 and Joe Profaci died in 1962. Men whose allegiance was to Gambino replaced each. By 1967, when Vito Genovese died, Gambino was left as a near boss-of-bosses. Gambino is known for running one of the most profitable crime families in history and for never having gone to jail. He remained in control of his family, with help from Paul Castellano, until his death in 1976.

It is not clear when Sinatra first became associated with Gambino. Sinatra was involved in at least two business deals with Gambino in the 1970s. Gambino also appeared in the famous photograph taken in 1976 at the Westchester Premier Theatre (one of their joint enterprises) along with Paul Castellano, Gregory De Palma, Thomas Marson, Aladena Fratianno, Salvatore Spatola, Joseph Gambino and Richard Fusco.

The business deals that Gambino and Sinatra were involved in together were:

1. Computer Fields Expressway – In 1970 Jack Pourtney, a stock broker at the 1st Williams Street Corporation in New York City, approached Richard Alpert about investing money in a company called Computer Fields Expressway. Alpert went to an acquaintance known to him as Joe Paris, real name Joseph Guarnera, to help him raise money to invest. Paris, who claimed to be a relative of Carlo Gambino, raised $100,000 allegedly from Gambino, Sinatra and Jilly Rizzo (a long-time friend and occasional bodyguard of Sinatra). The stock price for CFE dropped from $12 per share to $.75 per share. According to the FBI file the drop in the stock price was because Pourtney was stealing assets from the underwriting company, 1st Williams St. Corp. The FBI became involved, at the request of the U.S. attorney in New York, when Alpert charged that his life was threatened if he didn’t return the $100,000. By this time the Securities and Exchange Commission had become involved with the investigation and Pourtney cooperated with them. In February 1971, Alpert was subpoenaed to appear before a federal grand jury. He took the Fifth Amendment and refused to answer any questions. In March 1971, FBI agents questioned Alpert. He denied that his life had been threatened. He also denied that Frank Sinatra or Carlo Gambino had ever invested money in CFE.

Based on other deals that Sinatra was involved in it is likely that he invested money with Gambino in CFE. Whether Sinatra or Gambino invested the money in CFE, it is probable that Sinatra had no knowledge of or participation in the threats or the attempts to extort money from Alpert.

2. Westchester Premier Theatre – The Westchester Premier Theatre in Tarrytown, N.Y., began as a scheme by Gregory De Palma and Richard Fusco, members of the Gambino family. First there was an inflated stock scam, where stock was sold to "big names" such as Alan King, Steve Lawrence and Eydie Gorme for pennies on the dollar. The stock never drew much interest and there were several phony purchases and corporate purchases with kickbacks to executives. As a result the stock dropped to around $1 per share. The theater was built, with huge construction cost overruns, on a landfill owned by De Palma and Fusco in 1974. De Palma and Fusco, needing more money to keep their scheme afloat, convinced Carlo Gambino to invest $100,000. He did so only on the condition that Frank Sinatra be brought in on the deal. The theater opened in 1975 with a performance by Diana Ross who was paid $235,000. Fusco and De Palma ran the theatre as if it were a Las Vegas casino, skimming huge amounts from concessions and t-shirt sales and selling tickets for seats that didn’t exist. The theatre was huge and very well appointed. The biggest acts in show business were booked there and the gross for the first year was estimated at $5.3 million. But by December 1976 the theater was near bankruptcy. Only a run of performances by Sinatra and Dean Martin in May 1977 delayed the closing of the theatre.

Federal agents, investigating another matter, tapped the phone of Tom Marson, a friend and Palm Springs neighbour of Sinatra. They recorded a conversation between Marson and De Palma in which they discussed skimming cash from the upcoming Sinatra appearance at the Westchester Premier Theatre. The result of this conversation was 10 indictments handed down by a New York Grand Jury in June 1978. During the investigation it came out that Sinatra was paid $50,000 "under the table" for his first appearance there. Sinatra was never indicted.