Frankie was good…and bad

I cut my singing teeth on Frank Sinatra’s music. I’d say the majority of my “standards” style (for what it’s worth) was formed from listening to and trying to emulate his amazing ability to phrase a line. He was indeed the “Chairman of the Board” in that sense. Listen to “Only the Lonely” or “Guess I’ll Hang My Tears Out to Dry” and you’ll know what I mean.

While listening to one of the CDs in the Capitol Years collection on my way home from school yesterday, I thought about some of the interesting stories I’d read in Kitty Kelley’s tabloidish biography, His Way. It’s been years since I read it, but I recall it being, shall we say, not especially complimentary towards Mr. Sinatra. I think the lady downright hated him, and he must have sensed it. He sued to prevent her from publishing the book, but enter the First Amendment, stage left.

Ms. Kelley’s penchant for “unauthorized” biographies (and I use the term “biographies” loosely) reaches far beyond Frank. She’s done the favor for Nancy Reagan, Jacqueline Kennedy Onassis, the Bush family and others as well, so…

Anyway, back to Blue Eyes.

I decided to do a little research on him last night, after my work was done. I ended up spending an hour and a half reading Sinatra’s FBI file, and here’s what I found:

Francis was a bad boy.

It’s long been said that Sinatra hung out with mob thugs. Pictures have captured it, and phone calls have recorded it. But he denied any serious liaison with them to his dying day, and strangely, no charges ever really stuck. (Isn’t that the MO of most gangsters? Do enough to get noticed, but not enough to get caught.) His most important and dangerous link with organized crime was Sam Giancana, the Chicago mob boss.


According to FBI wiretap transcripts, Frank entered into several business deals as a front for Giancana, including the famous Cal-Neva resort on the California-Nevada border. Sam constantly wore a friendship ring Sinatra had given him. They vacationed together in Miami. Frank regularly performed gratis at two of Giancana’s “supper clubs,” which doubled as backroom gambling halls. To say they weren’t friends is to ignore the nose on your face.

So, why didn’t they fry Frankie for his ties to the mob? Turns out, he had friends in high places as well. Somehow, he was always able to slide out the back door. People who made him angry, however, weren’t so lucky.

Jackie Mason, a decidedly unfunny (in my opinion) borscht-belt comedian who worked the casinos in the sixties, got a face full of Sinatra acrimony, on three separate occasions. According to’s lengthy summary of the 1200-page FBI report:

…Mason angered Sinatra by making jokes about his marriage to Mia Farrow. Mason received phone calls threatening his life, but refused to change his routine. Six days later, three bullets were fired through the glass door of Mason’s hotel room in Las Vegas.”

I suppose it could have been the fault of a crazed fan. Or not. Mason joked the very next week that he didn’t know who shot at him, but he’d heard someone outside afterwards “singing doobie-doobie-doo.” That week: four more death threats. (Is this guy dumb or what?)


The coup de grĂ¢ce came in February of the following year:

“[W]hile Mason was sitting in a car in front of an apartment building in Miami, a man wearing brass knuckles yanked open the door and smashed Mason in the face, breaking his nose and crushing his cheekbone. ‘We warned you to stop using the Sinatra material in your act,’ the attacker said before leaving. Mason finally got the message and stopped using jokes about Sinatra.”

Well, ya THINK?

The stories go on and on and on, fiends. Over a thousand pages of stuff, and me with no time left. But regardless of Frankie Boy’s questionable friendships, shady business deals, and under-the-table gimmes involving gangsters, actors and politicians, he was still The Man With the Voice. The Kookiest of the Koo-Koo Hep Cats. That’ll never change.

Fink out.

3 thoughts on “Frankie was good…and bad

  1. Stein

    Often the most talented are the least likely to use their brains. ie. Chad Ocho Cinco, TO, Dennis Rodman, Jack-o, the list goes on… Frankie, like the other mobsters of the era, was nailed for something unrelated to the mob just so the feds could nail him for something. Al Capone, mass murderer, was arrested for tax evasion. Frankie was arrested early on for adultry. Yes, you could be arrested for that. If it was any other man he probably wouldn’t have been, but they knew of his mob record and nailed him.
    There’s a reason that there are actors, singers, musicians that succeed despite lacking talent. They use a great deal of heart, desire, and determination. Just take a look at William Shatner. He’s an AWFUL actor. (Have you ever heard him “sing?”) He makes it in the business because of his work ethic, at least until he got a name for himself. Michael Jordan was cut from his freshman basketball team in high school. He worked and worked and worked until he had trained himself to be talented, but it didn’t just come naturally. Talent, in my opinion, is overrated.


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