He was a raging lush
“Alcohol,” Sinatra once said — several decades before being buried in 1995 with a flask filled with Jack Daniel’s —
“may be man’s worst enemy, but the Bible says love your enemy”. In perhaps his most famous drink-related anecdote,
from 1967, Sinatra (whose first wife, Nancy Barbato, would lock herself in the bedroom if she saw the gin was out)
ran up a $500,000 gambling debt at The Sands, Las Vegas, disappeared for a weekend, came back inebriated, jumped
into a luggage cart with Mia Farrow (then his bride, 30 years his junior), crashed into the lobby window, and then
attempted to set fire to the lobby’s sofas and curtains.
This charge is undoubtedly a valid one, but he minimised its harm on his professionalism — he’d go cold turkey on
booze as well as cigarettes in the weeks before recording sessions to preserve his voice. Besides, should a man who
described himself as an “18-carat manic depressive”; who was possibly bipolar; who swapped life in a neighbourhood
he later called a “sewer” for a milieu soaked in high-glamour and hedonism; and who was hounded by the media and
authorities over six decades be vilified for self-medicating to the point of abuse?
He was an inveterate womaniser
Another one for the ‘Let he without sin cast the first stone’ file. It’s ironic that so much of Sinatra’s output
drips with loneliness (although Ervin Drake’s “It Was a Very Good Year” is kind of lustful nostalgia posing as
romantic revelry), for between (and during) four marriages — to Nancy Barbato, Ava Gardner, Mia Farrow and Barbara
Sinatra — Sinatra is rumoured (with varying levels of surety) to have squired notables including Marilyn Monroe,
Lauren Bacall, Jackie O., Marilyn Maxwell, Lana Turner and Joi Lansing. The highest profile affair was with his
second wife, Gardner, who once remarked that, “He’s good in the feathers” — during his first marriage.
It’s widely thought that amorous dispositions were a huge part of the bond between Sinatra and Jack Kennedy, forged
when the then Senator Kennedy went to Vegas while on the campaign trail and was introduced to Sinatra by Peter
Lawford, a Kennedy in-law. What Sinatra’s star power could do for Kennedy’s chances of election would surely have
been a draw for the 35th president-of-the-United-States-in-waiting. Indeed, had Sinatra not managed to get certain
underground figures (probably Giancana) to talk to coal unions in the crucial swing states of Illinois and West
Virginia… well, the butterfly-effect potential is mind-boggling.
It’s common in a court of law to establish the defendant’s character, and the extent of Sinatra’s non-creative
achievements are spell-binding. The Rat Pack were credited not only with saving Vegas from ruin — with tourism
failing to match up to construction in the mid fifties, they brought in the crowds — but also, eventually, prompting
a decline in racism in the city because of the power of black performers (on top of the aforementioned Mob incident,
Sinatra once threatened to leave town for L.A. over the treatment of black musicians, prompting other entertainers
to threaten the same).
It was a devotion to basic human decency that saw him set up a record label, Reprise Records, in 1960, incensed by
the way at which labels mistreated their artists. (In the process, he also helped keep his own genre — an evolving
hybrid of jazz, swing, saloon songs, show tunes and big band — going strong when that cultural tsunami that was rock
’n’ roll arrived on the scene. It’s impossible to overstate Sinatra’s importance to the musical canon: ironically,
for a recording artist listened to almost entirely via compilations these days, it was he — not The Beatles or The
Beach Boys — who can be called the Godfather of concept albums, meticulously selecting tracks that had a thread
running through them in terms of theme, mood and emotion.)
He struggled with crippling vulnerability as well as anger, the death of his idol, Humphrey Bogart, and the discovery
that Gardner, at a low point in a destructive marriage, had had two abortions perhaps being particularly devastating
moments. And yet it never crushed his insatiable creative ambition or his generosity. As well as giving money to the
civil rights movement (and influencing the Mob to do the same), during a 1962 international tour he raised over $1m
for children’s charities in every country he performed in.
Flawed? Yes. More flawed than the average person would be if immersed in Sinatra’s life experiences over the decades?
Impossible to say, but based on the mass of evidence we have, “considerably less so” is a perfectly reasonable
One would have thought this would have put paid to the communism rumours?
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