What Donald Trump’s Criminal Trial Reveals About a Potential Second Trump Administration

There’s a tape that both the defense and the prosecution played in summations in former President Donald Trump’s criminal trial. In it, you can hear the chaos of Trump’s office at Trump Tower in September of 2016: Trump seems to be having multiple conversations almost simultaneously. He talks to an unidentified person on the phone. He discusses polls with Michael Cohen, his executive vice-president at the time. Trump and Cohen talk about a diversity initiative and stopping the media from unsealing the records of Trump’s first divorce. His executive assistant pops in with word of a call from a developer. Trump calls for a Coke.

And then, very clearly, you can hear Cohen saying, “I need to open up a company for the transfer of all of that info regarding our friend, David, you know, so that — I’m going to do that right away. I’ve actually come up and I’ve spoken … I’ve spoken to Allen Weisselberg” — then the Trump Organization’s chief financial officer — “about how to set the whole thing up.”

Trump interrupts and says, “So, what do we got to pay for this, 150?” Then he says, “Cash?”

“No, no, no, no no,” Cohen says. “I got it.”

On the most literal level, the tape showed Trump discussing the logistics of paying off a woman who said she had an affair with him. This was key evidence for the jury’s ultimate finding that he had intended to alter the outcome of the 2016 election by making unlawful hush money payments.

When this tape was first made public, in 2018, it was hard to pin down exactly what it all meant. But as Trump’s seven-week trial proceeded, the broader meaning of the tape emerged in sharp relief: Everything is connected in Trump world, ethical borders are easily crossed and Trump is on top of every detail.

The verdict in the criminal trial provided answers to a narrow series of questions, not least of which was whether a presidential candidate had used illicit means to prevent voters from learning about a payoff to conceal a sexual encounter. (Trump has vowed to appeal.) But the trial also unveiled a broad array of evidence that went far beyond the charges. It revealed a lot about how Trump went about running his company and the presidency — and provided hints of how that might play out in a second Trump administration.

For most of Trump’s presidential term, I co-hosted the ProPublica/WNYC podcast “Trump, Inc.,” whose mission was to delve into the conflicts of interest between Trump’s business and his presidency. Because there was so much that journalists didn’t — and couldn’t — understand about a privately held company that clung tightly to its secrets, “Trump, Inc.” billed itself as “an open investigation.” We were candid about what we did and did not know because we lived in a world of doubt.

“Trump, Inc.” uncovered a lot, including unearthing Cohen’s dubious connections in 2018 and outlining how his role as Trump’s lawyer (then still intact) created a cloak of legal privilege that hid their interactions.

But we saw just tiny glimpses of the documents that have now been revealed in their entirety in the criminal trial; we had no access to the many Trump employees, current and former, who have now described, under oath, the inner workings of the Trump Organization.

That testimony confirmed what that tape seemed to show: that Trump pays close, close attention to all his business affairs, and always has. This, in turn, suggests that the mixing of Trump’s presidency and business that “Trump, Inc.” and others documented occurred under that same watchful eye. And if voters elect Trump a second time — this time knowing that he was convicted of a crime, one where key acts were committed in the Oval Office, on top of his two impeachments — Trump can conclude that America’s voters have blessed his way of doing business. There’s every reason to believe his conflicts of interest will only be more open and more unapologetic.

The Trump campaign did not respond to a request for comment.

Trump employees testified to his intense level of control in three trials against Trump or his company over the past two years. These were among five trials since 2022, each of which I covered in person, including the criminal trial of his company for tax fraud, two defamation suits brought by the writer E. Jean Carroll and the New York attorney general’s civil fraud trial. Each trial ended badly for Trump or his company (and each is being appealed).

Donald Trump’s criminal trial in New York offered one sharp revelation after the next. The disclosures came not just from the talked-about witnesses, such as former National Enquirer publisher David Pecker, Stormy Daniels and Cohen himself, but also from Trump’s former comptroller, his executive assistant and the aide who sat closest to the Oval Office. Some of these individuals, including a junior bookkeeper for the Trump Organization and the head of the company’s accounts payable department, work in Trump Tower to this day.

The picture that emerges from their testimony is of a boss — “The Boss” is what they nearly uniformly call him — who manages the tiniest of details but leaves the faintest of traces of all that management. Up until the throes of the 2016 campaign, Trump had to approve every payment over $2,500, an extraordinarily tiny sum for a mogul with assets around the globe. (For the duration of the campaign, until he became president, that amount inched up, to $10,000.) Trump would reject checks he didn’t want to pay and send them back to his underlings, with the word “VOID” scrawled on them in Sharpie.

Trump watched every expense in this way, his comptroller Jeff McConney testified. Trump once told him, early in his time at the company, “You’re fired,” because McConney hadn’t made an effort to reduce Trump’s bills before presenting Trump with payment documents. “It was a teaching moment,” McConney said on the stand. This close attention and tight-fistedness extended company wide: When it came to Trump University, Cohen testified, it was part of his job to offer a vendor 20% of what they were owed, or to pay them nothing at all.

Trump brought this ethos to the White House, where, as his lawyers liked to point out, he was the “leader of the free world.” He took time to write “PAY” on a $6,974 invoice sent by Trump Organization executive assistant Rhona Graff for an annual membership and “food minimum” at the Winged Foot Golf Club in Mamaroneck, New York.

Trump, of course, handed over control of the Trump Organization, including the oversight of its payments, to his older sons and Weisselberg at the outset of his administration. But he never gave up ownership of his company. He always made money from it, and does to this day.

And Trump, while president, went to extraordinary lengths to keep control of his “personal” checking account. That account actually belonged to a Trump Organization business entity, which underscored the lack of separation between Trump and the company he had ostensibly separated himself from. Trump’s personal checks were approved by Weisselberg; generated by Deborah Tarasoff, the head of Trump’s accounts payable department; stapled to the approved invoice; and sent via FedEx by Trump’s junior bookkeeper, Rebecca Manochio, to the Washington home of Trump’s bodyguard-turned-White House aide, Keith Schiller, who would bring them over for Trump to sign. That’s how the checks that Trump signed to Cohen made their way to the Oval Office.

“Checks came in a FedEx envelope” that Schiller delivered, testified Madeleine Westerhout, Trump’s director of Oval Office operations. “I opened the envelope. And inside was a manila folder with a stack of checks. And I brought the manila folder in to the president for him to sign.”

Money wasn’t the only thing Trump paid close attention to. He wrote all of his social media posts, save for a few written by an aide, Dan Scavino. Sometimes, Trump would dictate tweets to Westerhout. She would type them up, print them out and show them to Trump so the president of the United States could take time to scrutinize, and adjust, the punctuation. “He liked to use the Oxford comma,” Westerhout testified.

Trump did not send emails or text messages. This aversion has long been known, but the trial testimony laid out a whole series of ways in which Trump communicated without leaving precise documentation.

He was on the phone beginning at 6 in the morning and “late into the night after I went to bed, so I always felt guilty about that,” Westerhout testified. He’d often use Schiller’s cellphone to make calls, and employees would use that number to reach Trump. There were no Trump memos, no notepads, no Post-it notes, just an occasional Sharpie scrawl. And largely, except for Cohen’s, no testimony that what these employees did, they did “at the direction of” and “for the benefit of” Donald Trump. (This was an essential part of the judge’s charge to the jury: that Trump “personally, or by acting in concert with another person or persons, made or caused a false entry in the business records of an enterprise.”)

This is the backdrop for the conflicts “Trump, Inc.” and other news media covered while Trump was president. To recap some of them (at a moment when polls show many Americans have forgotten much of what transpired during his administration): Trump’s hotel in Washington became a must stop-by for foreign officials, earning his company millions. He caused the U.S. Treasury to spend more than $1 million to house Secret Service agents in rooms with top-of-the-market rates at Mar-a-Lago and had the government pick up the tab for $1,005.60 in cocktails apparently enjoyed by administration officials and friends at his resort’s bar.

During Trump’s presidency, the response to questions about all this went something like this: As a global businessman, he or his allies would say, how could he possibly pay attention to whether the presidential seal was used on his golf courses? Or whether his son, Don Jr., was trading on the name “Donald Trump” to sell condos in India. Or whether businesspeople with foreign ties were trying to make a buck, or millions, from his presidency?

Indeed, this was part of Trump’s defense in the criminal trial, and in the civil fraud trial at which Trump was ordered to pay hundreds of millions of dollars to New York state for what a judge found was a yearslong practice of lying about the value of his assets. When he testified at that civil trial, Trump distanced himself from the fraud: “All I did was authorize and tell people to give whatever is necessary for the accountants to do the statements,” he said. And the false statements of financial condition? “I would look at them, I would see them and maybe on some occasions, I would have some suggestions.”

As is his right, Trump chose not to testify at his criminal trial, but his lawyer Todd Blanche argued on his behalf that Trump “had nothing to do, had nothing to do with the invoice, with the check being generated, or with the entry on the ledger” and that he was so busy being president he maybe didn’t even look at the checks he signed. “Sometimes he would sign checks even when he was meeting with people, while he was on the phone, and even without reviewing them,” Blanche said during closing arguments.

The jury did not buy that defense.


Trump is currently leading in the polls. It’s entirely possible he will be elected president. Yet he’s continuing to aggressively pursue business deals in countries that will have a long list of issues on which they will be seeking U.S. support.

The Trump Organization entered a full-on partnership with LIV Golf, an entity majority-owned by the government of Saudi Arabia, for tournaments at his golf courses. And last year, a New York Times reporter and photographer visited what the reporter called a “multibillion-dollar project backed by Oman’s oil-rich government that has an unusual partner: former President Donald J. Trump.” The project was launched and is being built while Trump is the front-runner for a second presidency. But neither the Trump Organization nor the Trump campaign tried to defend or separate the project from the candidate who, while not running the company, still makes money from it.

“It’s like the Hamptons of the Middle East,” Eric Trump, who now runs the Trump Organization, told the Times. The paper wrote: “Oman, in fact, is nothing like the Hamptons. It is a Muslim nation and absolute monarchy, ruled by a sultan, who plays a sensitive role in the Middle East: Oman maintains close ties with Saudi Arabia and its allies, but also with Iran, with which it has considerable trade.”

It isn’t just the foreign deals. In April, right around the time Trump was about to be criminally tried in New York, he offered oil executives gathered at Mar-a-Lago “a deal,” the Washington Post reported. The publication summarized his message as: “You all are wealthy enough that you should raise $1 billion to return me to the White House.” In exchange, the Post said, Trump promised to reverse President Joe Biden’s initiatives to slow climate change, vowing to roll back some of them “on Day 1.”

And, as has been widely reported, with Truth Social going public, Trump has set up what Vox called “a perfect avenue for potential corruption.” As Vox noted, it’s “a way for Trump’s supporters to personally offer him financial support at a time when he desperately needs it.” By propping up the share price of the stock of the cash-hemorrhaging social media company, shareholders have potentially put billions of dollars in Donald Trump’s pocket.

It’s clear that Trump plays favorites and rewards loyalty; nearly eight years after he was inaugurated in 2017, it’s hard to imagine that any savvy businessperson or foreign leader fails to recognize this.

Certainly, those who were once in Trump’s orbit, if only briefly, testified to the dark side of that equation. Both Cohen and Daniels described the torrent of retribution they’ve experienced. Trump is unapologetic about his quest for vengeance. As he put it in one social media post last summer, “IF YOU GO AFTER ME I’M COMING AFTER YOU.”

Merely having been once employed by Trump seems to have taken a toll, on even relatively minor figures. In the civil fraud trial, Trump’s former comptroller, McConney, started weeping when he was asked why he no longer worked at the Trump Organization. He said he could no longer “deal with” the legal scrutiny he’d suffered. In the criminal trial, both former communications director Hope Hicks and Westerhout burst into tears on the stand, reflecting on their work history with Trump. Both said they remained loyal, but both had been banished from Trump’s graces.

And as for Weisselberg, he was not called to testify in this trial. His previous testimony in the trial of Trump’s company resulted in felony convictions on 17 counts and a five-month jail sentence. He is now serving a second jail sentence, in Rikers Island, for committing perjury in Trump’s civil fraud trial.

In the courthouse, Trump spent long stretches of time in an uncomfortable room with the shades always drawn, the fluorescent lighting unforgiving. He was required to listen to weeks of unflattering testimony, including, several times, to his own voice on that tape Cohen made of him, utterly cognizant of the tawdry deal he was striking. Saying, “So, what do we got to pay for this, 150?” After all the testimony in his criminal trial, this no longer seems like a random moment. It sounds like who Trump is: his attention to detail, his willingness to subvert the rules, the way he wields money to enhance his power, and vice versa, and is utterly unashamed.

The public knows all this now. In a second Trump presidency, it’s exactly what we’d get. Except this time, it will be all out before us, not in a secretly recorded tape.