Musings: The Mob Boss in Chief

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As I settled in to write this column, I was reading about the latest shameful updates from Pardon Watch 2021. With mere hours left on his presidency, and facing that prospect that he, his family and closest associates may all soon be swept up in a slew of state and federal investigations, Donald Trump is pondering one last brazen power grab. Rumors emanating from the West Wing suggest Trump is prepared to issue a slew of pardons, numbering over 100, on Tuesday before he leaves office.

While there is a range of thought on the constitutionality of a president pardoning themself, with most scholars considering it a no-no, it is well established that presidents enjoy sweeping pardon power, and its deployment in American history has drawn controversy and condemnation for Democratic and Republican presidents alike. 

But for folks who have observed Trump for a long time, this smacks of nothing more than the latest exhibition of his wanton desire not to be president, but to be the Mob Boss in Chief, feared by friend and foe alike, capable of browbeating and intimidating anyone into submission or fealty.

This obsession with mob figures has been evident in The Donald’s life since he was first making a name for himself with millions of his father’s dollars in the New York real estate game. He hired as his attorney the notorious Roy Cohn, a political fixer who became famous for his role in the McCarthy hearings in the 50’s but who, in later life, became a luminary in the dark underbelly of New York politics and crime.

It is somewhat remarkable that this chapter of Trump’s life hasn’t received closer examination. It was reported on during his 2016 presidential campaign, but that tiltawhirl of a campaign made it difficult for any story to spend more than a few minutes in the headlines before Trump’s next tweet washed it away.

Trump’s mob associations came back to light with the 2019 release of Martin Scorsese’s The Irishman. Trump either knew or worked with most of the prominent gangsters portrayed in the film, perhaps most notably the vicious Fat Tony Salerno. As detailed in Rolling Stone: “Salerno, who’s portrayed in the film by Domenick Lombardozzi, supplied the fast-drying concrete that built Trump Tower and other Trump properties. Salerno also controlled the local concrete workers union, and when a strike shut down construction in Manhattan in 1982, the one of the few buildings that wasn’t affected was Trump Tower.”

For someone as dogmatically obsessed with his own bottom line as Donald Trump, the ability of mafia bosses like Salerno to move mountains, either by bribes, threats, or beatings was something to be admired. 

It’s always been clear that Trump saw himself more as a mob boss than a political figure. He demanded loyalty, punished any perceived slight, and tried to run the federal government like an extension of his sham real estate empire. The choppier the waters got, the more like a deranged mob boss Trump seemed.

Indeed, in the final months of his presidency, after being roundly rejected by the American people and losing a slew of swing states including Georgia and Arizona to Joe Biden, Trump seemed to be channeling Tony Soprano as much as any historical precedent for how a president should behave.

He browbeat governors and secretaries of state, threatening their political futures if they didn’t carry out his orders. He began shuffling and reshuffling the deck of his legal team until the few remaining parts were reduced to Rudy Giuliani and a small rogues gallery of questionable attorneys. In a dark irony, it was Giuliani himself who grew to prominence prosecuting the very mob figures Trump adores, sending the infamous John Gotti to prison before ascending to the mayor’s office.

I’ve been contemplating the odd psychic connections between Trump and Tony Soprano for the past week, and aside from the obvious east coast connections, there is something clear and glaring about both men that may explain the Trump’s devolving psyche as he stares down the ego shattering prospect of leaving office on Wednesday. 

If you’ve ever seen The Sopranos you may remember that one of the central conflicts of the series was that Tony, falling out from panic attacks and terrifying his family, decides to see a therapist, a definite no-no in the secretive world of crime families. Much of Tony’s therapy in the early seasons focuses on his relationship with his mother, an admitted hellion, but overlooks a deeper source of psychological trauma that would dictate most of Tony’s life.

Much like Trump, Tony Soprano was born into a family business and always expected to enter it. While Soprano belonged to the underworld, Trump had the good fortune of being born into a more upper crust life. His real estate baron of a father set high expectations for his children, and when Trump’s older brother struggled to claim the family mantle due to a lifetime of addiction issues, The Donald assumed the reins. 

Despite their ascensions, neither was ever able to escape the expectations of their fathers. Tony Soprano would come of age and begin life as a small time wiseguy, working his way to the top of his family’s organizational chart. Trump, installed at the seat of his own empire with money gifted from his father, could also never break free of the constraints of his family name and business. When his own attempts to build a grandiose real estate and gaming empire began to washout in massive debt and bankruptcies, he would turn time and again to his father, draining the family estate of millions and millions of dollars to keep himself afloat.

Trump’s inability to keep from gambling his family fortune and future on a series of harebrained ideas like an airline and mail order steak company mirrored Tony’s own struggles with gambling and compulsivity. While Trump bet on high rises and golf courses, Tony bet on ball games and ponies. That may look different on the surface, but both reflect signs of compulsive behavior disorders that should serve as red flags for anyone running a multimillion dollar organization, or in Trump’s case, an entire country.

And now, Trump gets to know how it feels to live every day of his post presidency in the same almost hallucinatory worry that we watched Tony experience in the final scene of the series. Waiting for his family to join him at a New Jersey diner, Tony never fully settles in, his eyes scanning the room for the dangers he’s learned may be lurking over a lifetime.

Is that a cop sitting at a booth over his left shoulder? Is the guy at the bar in a members jacket a fed or a hitman? Are we ever really safe from the consequences of our misspent lives?

That tension unfolds and eventually leaves us to contemplate the outcomes when the bell above the door chimes, Tony looks up, and the series cuts to what feels like five minutes of a black screen.

In those final moments, Tony isn’t wondering if something will happen, but when. When will the other shoe finally drop? When will the feds rush in? Will they let me finish dinner with my family, or tear me away from the table? 

Where will they come from? When will it happen? What will finally bring this moment to pass?

Donald Trump always wanted to be a gangster. Now, as he rides off into his post-presidency faced with those questions, he gets to know how it feels to be one.

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