“The music was the engine of the life. If there had been no music, there would have been no immense obituaries and no televised farewells. To be sure, Sinatra was one of those figures whose art is often overshadowed by the life…In the end, only the work matters. Sinatra’s finest work was making music.”
From Pete Hamill’s book, Why Sinatra Matters.
The Chairman of the Board was one of Frank Sinatra’s nicknames, due in part to his vague connections to the mob world, along with his immense celebrity status and business sense.
“Sinatra established the precedent for major artists to take on record companies and manage their own business affairs. He founded his own record company, Reprise Records, in 1961 and demonstrated that artists could take artistic and business control of their own affairs. He contributed to an ethos of independence in celebrity culture and virutally pioneered the tradition of the popular vocalist as auteur.”
From the book Frank Sinatra, by Chris Rojek.
Well into the digital age, it’s interesting to consider what this superstar did in the early 1960s of the United States, when he wasn’t happy with his current industry arrangements – he started his own record label. But note the significant difference when compared to other artists who have started their own record labels: you’ve heard of this one, and it still exists.
Throughout his entertainment career, Sinatra accomplished a couple of things (from Sinatra.com): 11 Grammy Awards, Grammy Hall of Fame Award, Grammy Lifetime Achievement Award and Legend Award; Academy Award for Best Performance by an Actor in a Supporting Role, 1954 (From Here to Eternity); Kennedy Center for the Performing Arts Medal of Honor Award, 1983; Presidential Medal of Freedom, awarded by President Ronald Reagan, 1985; Congressional Gold Medal, 1997; Inducted into the Big Band and Jazz Hall of Fame, 1980; Lifetime Achievement Award from the NAACP, 1987; 3 stars on the Hollywood Walk of Fame; Honorary Doctor of Engineering degree from the Stevens Institute of Technology, 1985; performed on more than 1,800 musical recordings and amassed an annual income estimated at the end of his career in the tens of millions of dollars; this includes income from concerts, recordings, real estate ventures and holdings in several companies, including a missile-parts concern, a private airline, Reprise Records, Artanis Productions and Sinatra Enterprises.
And then there’s the mob.
No assumed indictments here, just some info as best as we have it recorded today. Of course, no one outside the actual mafia circles of communication (including the CIA and FBI) really know what occurred in most of these situations. Either way, there’s plenty of info/evidence to know that Ol’ Blue Eyes was in on some level.
From Anthony Bruno’s article, “Frank Sinatra and the Mob,” from TruTV.com,
“On February 10, 1961, FBI Director J. Edgar Hoover sent a pointed memo to United States Attorney General Robert F. Kennedy, regarding singer Frank Sinatra’s extensive connections to organized crime figures…Special agents had been keeping tabs on the singer since 1947 when he took a four-day trip to Havana and painted the town red with a gaggle of powerful Cosa Nostra members who had gathered there for a mob conference. Hoover’s unstated message to the attorney general in that memo was as subtle as a sledgehammer: Look who your brother, the president, has been hanging around with. In fact, Sinatra had been an avid supporter of John F. Kennedy in the 1960 presidential election, and they had become quite close.”
John Clore 
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I don’t remember reading much about Sinatra and JFK’s relationship, but I do recall a book that claims mafia involvment in JFK’s assination. Read “I Heard You Painted Houses”. It’s about the Teamsters/Hoffa in Chicago. The Irishman claims to have handed off the very guns that were suspect in the assination. Even more interesting, if Sinatra was in contact with the mob (or better yet, a wiseguy himself) and a “friend” of JFK… and the mob assinated him… and his brother Robert (who fought his entire policital career against the mob to out all members)… WOW, there’s all kinds of ideas there.
Love it! Thank you, Amber. Glad to know you’re as interested in this “world” as I am. I agree, all kinds of ideas and story angles there. Thanks for reading.
John Clore