Since Donald Trump took office in January, many Ukraine-watchers have been stunned by the US president’s extortionary tactics with regard to Kyiv.
First, he pressured Ukrainian President Volodymyr Zelensky to sign a deal for extracting minerals, a deal that would essentially force Ukraine to repay with usurious rates what the Biden administration had offered as a gift. Then, when Zelensky came to Washington on Feb. 28, he was reprimanded for publicly making his case for real security guarantees and fact-checking Trump’s lies. As if the scolding weren’t enough, Zelensky was skewered by the US president and his henchmen for not being sufficiently obsequious.
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Flabbergasted commentators all over the world observed that Trump was behaving like a mafioso bent on solidifying his protection racket.
But to anybody who has been following Trump for the past half century, it’s no surprise.
A New York frame of mind
I’m a native New Yorker. Like all New Yorkers of my generation, I remember Donald Trump when he was a flamboyant young real estate mogul on the rise.
There’s one thing about Trump that I and my fellow New Yorkers have noticed over the decades: His modus operandi has not changed much. He has merely extended his audience and influence across the globe.

Wild Horses
In the 1980s I worked briefly for a Manhattan real estate company. But for much of the decade, I was a painter and small-time painting contractor. In both job circles we heard a lot about Trump. The stories from other small-time contractors were consistently similar. Trump would sign a contract for work on one of his properties. When it was time to pay the final 20 or 50 percent installment, Trump or his general contractor would say something to the effect of: “I’m not satisfied with the work. I’m not going to pay.” The contractor would protest. “But you have to, it’s in the contract.” Trump would shrug his shoulders and say: “You don’t like it? Sue me.”
Knowing that Trump had more money and access to lawyers, the contractor would be forced to accept the unilaterally imposed discount.
These were just stories I’d heard from other contractors, but USA Today did a deeper dive, and it’s clear that similar deadbeat methods were also employed in Atlantic City and Florida as the Trump real estate empire expanded.
Now he’s working the same angles with Canada, Mexico, Denmark, and, of course, Ukraine.
Flirting with the mob
To suggest that Trump is behaving like a mafioso is somewhat of an oversimplification for New Yorkers.
Trump, a dyed-in-the-wool New Yorker, most certainly had extensive interaction with Italian and Russian organized crime in his city.
The key conduit to his relationship with mobsters was the infamous lawyer Roy Cohn. A consummate New Yorker himself and the rich son of a prominent judge, Cohn rose to fame in 1951 as Senator Joseph McCarthy’s attack dog during the anti-communist witch hunts for which McCarthy was eventually censured.
The 27-year-old Trump met Cohn in 1973. Cohn, a closet-homosexual with a penchant for WASPy blond rich boys, took Trump under his wing.
By the end of the 1970s, the ruthless lawyer’s client list included not just the cream of New York’s high society and political world, but also the heads of New York’s Genovese and Bonanno organized crime families – Anthony “Fat Tony” Salerno and Carmine Galante respectively. Cohn also had connections with Gambino crime family boss Paul Castellano and his successor, John Gotti (the man who ordered Castellano’s murder in 1985).
As an aspiring real estate mogul, Trump had to negotiate the shark-infested waters of New York’s mob-controlled building industry. The New York crime families controlled both the concrete business and the construction workers’ unions. The Mafia in New York could extort any real estate developer they chose by simply ordering delays on concrete deliveries or work stoppages through the labor unions. Trump was especially vulnerable because his famous Trump Tower was built with fast drying ready-mix concrete rather than the more expensive methods used in the steel-girder skyscrapers typical of the 1980s.
Roy Cohn served as Trump’s middleman to help “grease the wheels” of his construction projects in that extortionary climate. In fact, in 1982 the Teamsters Union ordered a citywide strike – but the concrete work continued at Trump Tower.
Cohn also helped with regulatory issues when Trump expanded into the casino business in Atlantic City.
Through the same network, Trump managed to solidify links with Russian organized crime making headway in the city. In 1984, Russian mobster David Bogatin allegedly teamed up with Michael Franzese, a member of New York’s Colombo crime family to buy six condominiums in Trump Tower by laying $6 million in cash on the table.
In short, Trump rose to wealth and fame in a climate of systemic corruption perpetuated by entrenched organized crime. Thanks to Cohn’s mentorship, Trump learned how to “work the angles.”
After Cohn died of AIDS in 1986, Trump employed all the lessons learned from his mentor – arguably America’s greatest Mafia lawyer. One of the most invaluable lessons Trump learned was to always remain vague, even contradictory, when speaking in public so as not to incriminate himself. Trump appears to have mastered this lesson and made it a cornerstone of his political methodology.
The world is stunned. New Yorkers knew what was coming.
Mafia-state envy
Russian opposition leader and former chess champion Garry Kasparov famously tweeted a well-worn Russian joke: “Every country has its own mafia. Putin’s Russia is the first where the mafia has its own country.”
The mafia-like structure of government under Putin is well documented. The Russian president is suspected of having ordered the murder of numerous journalists and opposition figures. Intelligence specialists concur that Putin’s rise to power was likely due to false-flag apartment bombings allowing Russia to launch the Second Chechen War.
In all fairness to Trump, even though the US president behaves like a mafioso and his business career is littered with mafia connections, he has never been directly connected to mob-style murders the way Putin has. Indeed, even as president in his first term, Trump appeared to be averse to launching any lethal military campaign. His claim of having defeated ISIS in Iraq is misleading, since the military action was actually initiated by President Barack Obama years before the recapture of Mosul in 2017.
As such, one might take Trump’s claim of wanting to “stop the killing” in Ukraine at face value. Yet one mustn’t be overly naïve. He clearly and openly hopes to re-establish good relations with Moscow – primarily economic – notwithstanding Russia’s crimes.
Perhaps another consummate New Yorker, actor Robert De Niro, could offer some insight. In a vitriolic diatribe written for the 2023 Stop Trump Summit, De Niro wrote:
“I’ve spent a lot of time studying bad men. I’ve examined their characteristics, their mannerisms, the utter banality of their cruelty. Yet there’s something different about Donald Trump.”
De Niro views Trump not as a “bad” man, but as “evil.” He explains the difference:
“Over the years, I’ve met gangsters here and there. This guy [Trump] tries to be one, but he can’t quite pull it off. There’s such a thing as ‘honor among thieves.’
Yes, even criminals usually have a sense of right and wrong. Whether they do the right thing or not is a different story – but – they have a moral code, however warped.
Donald Trump does not. He’s a wannabe tough guy with no morals or ethics. No sense of right or wrong. No regard for anyone but himself – not the people he was supposed to lead and protect, not the people he does business with, not the people who follow him, blindly and loyally, not even the people who consider themselves his ‘friends.’
He has contempt for all of them.”
It would seem that De Niro, like so many New Yorkers who loathe Trump, would agree that the US president is not really a mafioso. Unlike Putin, Trump literally lacks the killer instinct to cold-bloodedly murder his rivals.
If that’s the case, then Americans, as Trump’s methods become increasingly clear, must decide: What is better for a superpower: to be led by an actual mafioso, or someone who behaves like one by dint of ingratiating himself to such gangsters?
De Niro is unequivocal: “We New Yorkers got to know him over the years that he poisoned the atmosphere and littered our city with monuments to his ego. We knew firsthand that this was someone who should never be considered for leadership.”
Unfortunately for the world-order established over the past 80 years, American voters have unwittingly chosen to allow both the mafioso and his envious admirer to divide the spoils of the world they inherited.
The world is stunned. New Yorkers knew what was coming.
The views expressed in this article are the author’s and not necessarily those of Kyiv Post.
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