For all of Donald Trump’s sound and fury and conspiratorial nonsense about his New York criminal trial, in the end his greed was the driving force behind his conviction.
In a historic trial focused on exactly what the real-estate tycoon turned president did to ensure a porn star wouldn’t dish about what she said was their extramarital sexual affair, the irony is that the road to conviction was paved with Trump’s miserly reluctance to pay.
In the reality-bending Trump era, it should come as no surprise that this tale reads like a Charles Dickens novel. In act two, there’s even a Scrooge-like reduction of a man’s Christmas bonus.
Trump refused to pay women with claims about infidelities that could have toppled his 2016 presidential campaign. He refused to repay the watchful media executive who guarded his reputation. He refused to pay a business vendor that would have had nothing to do with this fraud scandal were it not for a peculiar sequence of events. And he repeatedly refused to pay his own lawyer, allowing resentment to build until it blew up in his face.
As prosecutor Joshua Steinglass put it to jurors on Tuesday, it was Trump’s style after 40 years in business “to be involved in everything, even negotiating the price of the lightbulbs.” Steinglass credited Trump’s “frugality” with giving investigators some of the evidence they needed.
But it was his negotiation neurosis that would be his undoing.
The go-to argument for indignant Trumpists is that there’s nothing illegal about paying someone to shut up. The best counter is that Trump could have done it half a dozen other ways, but didn’t. Instead, his penny-pinching led to a convoluted reimbursement scheme that resulted in 34 felony counts of falsifying business records—all of which resulted in a declaration of “guilty.”
Trump made his guiding philosophy clear in his 2004 book, Think Like a Billionaire, which was reviewed by jurors and includes a chapter called “How to Pinch Pennies.”
“Always question invoices and never accept a contractor’s first bid. Negotiate! Negotiate! Or get out,” Trump wrote.
Or maybe that was his ghost writer, as his lawyers implied. Either way, Trump lived by those words.
Although the case originated in Trump’s alleged hotel rendezvous with Daniels during a Lake Tahoe golf tournament in July 2006—which he still denies—Trump’s first relevant act of greed can be traced back to an episode in January 2014, when Trump was laying the groundwork for his presidential run.
Trump had his consigliere, Michael Cohen, hire a tech firm called Red Finch to rig a CNBC poll about the nation’s top business leaders—only to stiff the vendor, refusing to pay its $50,000 bill when Trump was disappointed with the results. A year later, Cohen pulled $20,000 from his own bank account and handed the firm a paper bag filled with cash. He would admit pocketing the other $30,000 when Trump eventually repaid him but nonetheless, Trump had started to run a tab on his own lawyer. It would come back to haunt him
Fast forward to summer 2016, when former Playboy Playmate Karen McDougal had Beverly Hills lawyer Keith Davidson start shopping her story about an affair with Trump, which he also denies.
It started with a June 7, 2016 text Davidson sent to National Enquirer editor Dylan Howard saying, “I have a blockbuster trump story.” By the end of the month, Howard had met McDougal and determined her story was worthy of a catch-and-kill operation. His boss, American Media Inc. CEO David Pecker, approved a $150,000 deal that would give McDougal a fake writing gig at the supermarket tabloid. And Trump, the leading Republican presidential candidate, had taken a call from Pecker that he patched through the speaker on his desk at Trump Tower, allowing Cohen to recall his boss promising, “No problem. I will take care of it.”
But he didn’t. Pecker grew increasingly impatient as it dawned on him there was no way he’d get away with such a suspicious corporate expense on the company books. As Cohen would testify, the shared anxiety reached a breaking point that compelled Cohen to secretly record a conversation with Trump about the overdue bill—a tape Cohen supposedly planned to share with Pecker to ease his concerns.
By the time Davidson reached out to Howard for a second payday, this time to silence adult film star Stormy Daniels, the tabloid would not carry Trump’s water. Instead, Howard passed Davidson to Cohen.
Faced with what sounded like a bald-faced extortion racket in the closing weeks of a struggling campaign, Trump played games once again. He tasked Cohen with taking care of the problem but together they came up with a plan to drag it out, past the election if they could. With a month to go, Cohen struck a deal to pay Daniels $130,000 but came up with all kinds of excuses for not wiring the money. The career shyster feigned being too busy, disappeared for a time, blamed a Jewish holiday, and repeatedly claimed he’d lost bank account details.
When Daniels’ lawyer threatened to call the deal off, Trump was nowhere to be found—forcing Cohen to draw the money from his home equity line of credit and set up a shell corporation.
The lies kept stacking up. But they hadn’t yet reached the point of criminality.
The tale reached its second act after the 2016 election. As president-elect, Trump was jubilant. The business tycoon who leveraged his fame to launch a TV reality show and fuel a meteoric rise in national politics had become a parody of the American Dream. But he had a dirty little secret, and his loyal bagman was owed a pretty chunk of change.
It’s all the more confounding, then, that one of Trump’s final acts as head of the Trump Organization was to stiff Cohen of his annual bonus.
Every year, near Christmas, the boss would flee Manhattan for his Florida estate. As he did so, his employees opened envelopes to discover their reward for remaining loyal. When Cohen got his, he did a double take. His usual $102,000 had been cut by two-thirds. He stormed into Allen Weisselberg’s office, giving the chief financial officer a piece of his mind.
“I was truly insulted. Personally hurt. Didn’t understand it. Made no sense,” Cohen recalled on the witness stand, angry still, all these years later.
The guy who’d scour news articles to make sure the boss wouldn’t get maligned, the guy who’d phone reporters and threaten to sue and make their lives a living hell, the guy who stuck his neck out time and again to defend the honor of a fundamentally dishonorable man, was starting to realize this was a fool’s game. But not quite yet.
“Allen said, ‘Take it easy. We’re gonna do right by you. We’re gonna make sure you’re taken care of. Relax. We’ll make this right.’”
But instead of immediately reimbursing Cohen the $130,000, Trump and Weisselberg approved a drip-drip approach – paying Cohen much more, $420,000, but stretching payments across 2017, under the guise of legal work and with Cohen described as “personal attorney to the president of the United States.”
In the end, the payments produced 11 invoices, 11 checks, and 12 ledger entries—34 documents in all, ultimately the subject of 34 charges and determined by a jury of New Yorkers to be false business filings as defined by Penal Law §175.10.
Had it been a single fake invoice, Trump would have faced three felony counts—if the Manhattan District Attorney’s Office had bothered to take up the case.
Instead, Trump has shelled out tens of millions of dollars, paying lawyers Todd Blanche, Susan Necheles, and Emil Bove to defend him in a one-year case and a historic seven-week trial, redirecting political donations that could have supported his 2024 campaign but were instead burned in a futile effort to stop him becoming the first American president turned convicted criminal.
“I believe in spending what you have to,” Trump – or his ghost – wrote in his 1987 book, The Art of the Deal. “But I also believe in not spending more than you should. I never threw money around.”
Ultimately, he did. Just not soon enough.
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