Two American Originals, Two American Hellraisers

“You know…it’s just that people like this…they get all they want so they really don’t understand, you know… about a life like Frank’s.  I mean, when you’ve loved and lost the way Frank has, then you, uh, you know what life’s about.” — Tommy Pischedda – limo driver, “This is Spinal Tap”

“I’ve never killed a man, but I’ve read many an obituary with a great deal of satisfaction. — Clarence Darrow

Is our country coming apart?  The economy in shambles, scraggly protesters have taken to the streets to denounce what they say is a mal-distribution of wealth orchestrated by greedy bankers and their corporate handmaidens.  Stomach-turning stories of child-molesters and deranged murderers dominate the headlines – day after day after day…not to mention the crooked, inept politicians and insecure, drug-addled celebrities on constant parade through the courts.

Yet, as much as much as some might argue the darker features of this uncomfortable national moment – this trying epoch of public perversion and economic uncertainty – belong uniquely to our generation, history reminds us that our American story has traveled many of these squirrely roads before.

Before Kaycee Anthony and Jerry Sandusky there was Nathan Leopold and Richard Loeb and Thalia Massie.  Before Lindsay Lohan and Charlie Sheen, there was Judy Garland and Lana Turner and, well, there was Frank.

Before the Occupy Movement, there were the Pullman and United Mine Workers strikes and the vicious Pinkerton thugs that set upon the strikers, the closest time this nation has come to knowing real anarchy.

The context of that raucous heritage is the great gift of history – or good biography – and it is thanks to two equally sterling stories of two truly original American characters that we can take some comfort in knowing that our national fabric is quite resilient indeed.  In “Frank: The Voice,” by James Kaplan (Doubleday, 786 pgs) and “Clarence Darrow: Attorney for the Damned,” by John A. Farrell (also Doubleday, 561 pgs), we are reminded that crooks and malcontents and vice and perversion are pre-biblical realities of the human condition, just as extraordinary God-given talent is quite often and inexplicably thrown into that messy stew.

In “Frank” and “Clarence Darrow,” Kaplan and Farrell have written darned fine and fascinating books about two incredibly-gifted and deeply-flawed American characters and the times in which they lived — and even helped define.

Although born a generation apart and having made their mark in very different venues of national life,  Clarence Darrow and Frank Sinatra were each true American originals, sui generis, archetypes who wrote the playbooks for the F. Lee Baileys, and Elvis Presleys that would follow.

At first blush any similarities between the lawyer and singer may not be obvious.

Sinatra was East Coast ethnic, an Italian from mobbed-up Hoboken.  An only-child momma’s boy, his domineering mother loomed large throughout this career and relationships.  While certainly anything but a monk, Sinatra maintained a loose and wary reverence of the Catholic Church throughout his life.  Darrow, on the other hand, was from old American Protestant stock, albeit of the poor Midwestern variation, the fifth in a family of eight children in an austere and emotionless home. His mother died young, when the lad was in his teens.  When it came to organized religion, the avowedly atheist Darrow was having none of it.

But beyond both being self-made in the truest sense, there are other striking commonalities.  Domineering, bullying, and convinced of their greatness and superiority to their professional peers, they were confident in the extreme.  Civil rights supporters, each harbored sympathy for the “little guy.”  They were both hellraisers and iconoclasts, callous and ruthless, but possessors of a queer combination of compassion and a level of personal insecurity that kept them forever fearful of failing, and working, desperately working on their craft until the very end.  They hated to be alone and were serial philanderers.  Despite being the epically best at what they did, both encountered rocky professional and financial times that jeopardized their careers and legacies.

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As John A. Farrell put it about Clarence Darrow, “he was a Byronic hero – intelligent, captivating, jaded, moody; a renegade, with small regard for rank or privilege.”

The 1890s Chicago where young Darrow met his rise was a political ground zero in graft and corruption, with a city government run by “a low-browed, dull-witted, base-minded gang of plug uglies, with no outstanding characteristic beyond an unquenchable lust for money.”[i]  It was a town of bosses and kingpins, with central-casting names like Michael Cassius “King Mike” McDonald, Joseph “Chesterfield Joe” Mackin, Michael “Hinky Dink” Kenna and John “Bathhouse” Couglin.

The booming Midwestern berg was also an epicenter of vice and desperate poverty and famously grim working conditions for the ranks of children and immigrants toiling in slaughterhouses and railroad yards.[ii]

Darrow’s ascent in Chicago’s varsity game of politics and law was meteoric.  The networking skills of the boy from Ohio made him a key aide and advisor in swift succession to Mayors and Governors.  But it was his rare gift for oral argument that was the real sight to behold. He literally was the attorney who could bring juries to tears – even if they voted to hang his clients.

Darrow’s increasing progressive-socialist bent greased his ultimate path from the insider’s corporate attorney (for the railroads, no less) to the “attorney for the damned”[iii] who took on thankless, politically unpopular cases.  “No era of the world has ever witnessed such a rapid concentration of wealth and power as this one in which we live,” he said, and “if the underdog got on top he would probably be just as rotten as the upper dog, but in the meantime I am for him.”

His cynicism toward the American power structure led him to represent such toxic clients as Eugene Debs in the Pullman strike case, the McNamara brothers (anarchists charged with bombing the Los Angeles Times Building), and the thrill-killing Leopold and Loeb, the Charles Mansons of their day.  Then, of course, there was the Scopes “Monkey” Trial, the legendary face-off between Darrow and an aging William Jennings Bryan, with the outspoken atheist Darrow naturally taking the defense of the teacher who had introduced the concept of evolution into his Tennessee classroom.

For all his intellect and profound gifts as an advocate, as his career wore on, Darrow was increasingly blinded by a crass and competitive nature that often twisted his judgment and ethics.  This led to serious allegations of bribing jurors and later, severe personal financial distresses that compounded his need to take cases – any cases. So at seventy-three he came back to the courtroom essentially as the mob’s hired legal gun to defend underworld figures including William “Three-fingered Jack” White, John “Dingbat” Oberta, and George “Bugs” Moran, as well as the grand dragon of the Indiana Ku Klux Klan, David Stephenson, who had been convicted of torturing and murdering a twenty-eight-year-old female social worker.

In addition to the Stephenson case, Darrow’s progressive street cred took another hit when, in 1931, for the then-unheard-of sum of $30,000, he agreed to represent Tommy Massie and two others charged with the brutal lynching of a young Hawaiian native accused of raping the Navy officer’s troubled wife, Thalia.  Given the widespread belief that Thalia had fabricated the tale and unfairly fingered a gang of brown-skinned locals, the long-time NAACP board member’s reputation took a significant and lasting hit among national civil rights leaders.  As Farrell put it, “most of all he took the case because he needed the money.”

Frank Sinatra, too, certainly took plenty of gigs “for the money,” and Kaplan’s book (covering the singer’s early years up until the late 1950s – a second on Sinatra’s later career is forthcoming) details some of his less-glorious moments.  Kaplan’s “Frank” is also full of surprises for those not expert in the life of the singer.  A few:

  • His mother was a politically-connected ward leader who conducted abortions for extra money (in the twisted irony category, abortion would go on to be something of a leitmotif for Sinatra as both his first wife Nancy and second Ava Gardner had one and two abortions respectively, despite Frank’s stated, if half-hearted objections).
  • He had a violent and traumatic birth.  Sinatra’s head and face were badly damaged thanks to sloppy forceps work by the attending physician; the scars – literally and figuratively – stayed with him for life.
  • During the war, his draft status mysteriously went from A-1 to 4-F, attributed to a “punctured eardrum.”  When this became public knowledge, angry GIs hurled tomatoes at the singer’s name on playhouse marquees.
  • Sinatra’s played a truly critical role in the creation of Las Vegas (along with Meyer Lansky and Frank Costello).  “In a very real way, Sinatra built Vegas: not only was he present at the creation, but he was responsible for it.”
  • He was obsessive compulsive and washed his hands twenty-five times a day

In addition to being the first real American pop icon to make young girls swoon – the Elvis before Elvis – Sinatra was also the first Brittany, the first Charlie Sheen.  At times he was a wreck, a major boozehound and pill-popper for much of the late 40s and into the 50s, at least twice trying to take his own life in fits of depression and drug-induced melancholia. He constantly got into fisticuffs and was known to keep handguns nearby.  The carousing and debauchery is, at times, quite unbelievable, and it often ended the singer up in the newspapers as well as court.[iv]

In “Frank,” Kaplan brings us a who’s who of Hollywood hotties from the Golden Era passing their way through Sinatra’s life if not his bedroom: Lana Turner, Angie Dickinson, Shelly Winters, Lauren Bacall, Ethel Merman, to name a few.  And, of course, there was Ava Gardner, the voracious and volcanic beauty who broke Frankie’s heart and nearly sent him over a cliff.

This rocky Gardner romance, along with booze-fueled flashes of public rage, changing American tastes, extravagant spending (on everything but his taxes) and Sinatra’s penchant for associating with “connected” characters in Vegas and Havana brought the singer to a near career-ending moment in the early 1950s.  And then, as Kaplan brilliantly recounts, through great effort and intrigue, Sinatra secured the role of Maggio in “From Here to Eternity,” the Academy Award-winning performance that would rejuvenate his foundering career and reputation.

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Both “Clarence Darrow” and “Frank” remind us how much things both great and small have changed in our society over the last century (small example: Sinatra was rarely photographed in anything but a full suit of clothes and, better yet, a dinner jacket when holding court at the Sands or the Copa) but they also underline how the human condition itself has not.  And they teach us that while America’s story is an untidy and unfolding one, the country we have inherited is, despite our many challenges, a more stable, transparent and fairer place than at any time in its blessed history.

***Author’s note: Through my Googling and phone calling research, I have not yet come across any evidence that Mr. Sinatra ever performed nor did Clarence Darrow ever try a case in our fair state (although Salesianum graduate Sean Reilly (an Irish guy? really?) is an award-winning Sinatra impersonator).


[i] Five-term Chicago mayor Carter Harrison Jr. (p 45)

[ii] “First in violence, deepest in dirt,”…”a mining camp, five stories high,” …”City Hall … is filled with brothel-keepers, saloon keepers and prize fighters, ready to barter the rights of citizens for a song”…”A stranger’s first impression of Chicago is that of the barbarous gridironed streets, his second is that of the multitude of mutilated people … the mangled remnant of the massacre.” (Lincoln Steffens and George Ade, the British Socialist John Burns, and a “British visitor” respectively (pp 35-36)).

[iii] Journalist Lincoln Steffens coined the term

[iv] Booze – serious amounts of it – was a constant for Sinatra and his retinue during these years. Examples: “There were times, at five or six in the morning, when he had to pour another Jack Daniel’s…” “Maybe I’ll come by and we’ll have a couple of drinks, and then some broads, and who knows?” “All of a sudden the doorbell rings.  It’s a delivery boy with more liquor.” (p 594) “He was in a kind of fever, consuming coffee and pills and cigarettes instead of food,”…”he was a walking wreck – walking around Jimmy’s apartment in his pajamas, a drink in one hand and a cigarette in the other…” (p 563) “Both of them [Sinatra and Gardner] could hold a lot of liquor. After he went back into the house and gave the bartender a $100 bill for a fifth of Beefeater, they got in his Cadillac and set off.” (p 372)

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About the Contributor

Michael Fleming

Michael Fleming

Wilmington resident Michael Fleming is a marketing and communications executive.

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