Day 12 of the Hush Money Trial: What Would Jail Be Like for Trump?

No, this account is not about Stormy Daniels’ wildly entertaining testimony. You’ll get the full story on that tomorrow.

Friday, May 3, was deadly boring in the courtroom—but also deadly for Donald Trump’s defense team, which had hoped to prevent a mound of highly incriminating documentary material from being entered into evidence. By the end of the day, the former controller of the Trump Organization and the current accounts receivable supervisor—both still on the reservation with their legal expenses paid by Trump—authenticated the checks, ledger entries, and invoices that make up the 34 counts of falsifying business records in the Manhattan District Attorney’s indictment.

But stultifying Day 12 began with high drama when Judge Juan Merchan warned the 45th president that his 10th violation of the gag order would be his last or he’d be sanctioned with jail time.

Merchan told Trump that he was well aware that “you are the former president of the United States and possibly the next president as well.” He said that he understood that jailing Trump “would be disruptive to the proceedings.” The Colombian-born jurist also said he worried about the court officers, corrections officers, Secret Service, and other law enforcement personnel who would be involved in Trump’s incarceration.

“The magnitude of that decision is not lost on me,” Merchan said. “But at the end of the day, I have a job to do.” Trump’s offenses, he noted calmly, represented “a direct attack on the rule of law, and I cannot allow that to continue.”

In March, I argued that the most appropriate punishment for the sociopath on the loose would be to make him pick up trash. I reprised my Old Goats argument yesterday in The New York Times, but by the end of the day, I was favoring incarceration.

My new courtroom friend, George Grasso, a former cop and retired city judge who attends court as a spectator, told me that the requirements of protecting a former president outdoors for hours on end would be a nightmare for the Secret Service. It occurred to me that Trump, in an orange jumpsuit, would make him an easy target from a high building. It wouldn’t be so horrible if Trump accidentally choked on a pretzel, as George W. Bush once did, but someone harming him physically would be a bad thing for the country. 

Society’s task is to bring Trump to justice and make sure he is not re-elected president, and if he can be disgraced and humiliated in the process, all the better. But we shouldn’t encourage or even hope for violence. That’s Trump, not us.

What we must do instead, as the judge noted, is stand up for the rule of law. In this case, that means jailing him if he opens his yap one more time to attack witnesses or the jury.

Where would he do his time? Until recently, it might have been at the huge jail next door, “The Tombs,” an infamous dungeon that made Rikers Island look like Mar-a-Lago. Unfortunately, the Tombs was razed last month, so the most likely place for Trump to spend a night or two is a holding cell on the 16th Floor of the Manhattan Criminal Courthouse, one floor up from the courtroom. 

While Trump would enjoy a “solitary” instead of sharing a larger cell with other inmates, the accommodations are satisfyingly unpleasant. The bed, if you could call it that, is narrow and hard, with the harshest blanket Trump has ever slept under and a sheet thread count one-tenth of his usual 500. Instead of a gold-plated commode like the ones that Trump enjoys at his many homes, the former commander-in-chief would find a clogged metal toilet hole without a seat. 

Thanks to the watchful presence of the Secret Service, Trump would likely be allowed to skip the standard practice of turning over his belt and shoelaces to prevent a suicide attempt, a procedure that did not help his friend and fellow man-on-the-make, Jeffrey Epstein. In this regard, Trump would be more fortunate than we reporters, who must take off our belts and watches to get through two metal detectors every time we enter the building. So, the first week of the trial, I decided to go belt-less, which makes my low-slung pants resemble those of the hand-cuffed defendants I’ve seen led through the halls.

While it’s unlikely we would catch a glimpse of Trump in an orange jumpsuit, there’s always hope. In 1928, an enterprising photographer lied his way into the execution chamber with a camera tied to his toe and got a famous shot of Ruth Snyder in the electric chair. 

For Trump, the most onerous part of his incarceration might be the disruption of his morning ritual. Trump said last month that it would be his “great honor” to be jailed by the judge, whom he routinely calls “crooked.” But some things are more important than honor—like hair. Absent his hairdresser and product, how would he show up in court the next day without dreaded “bed head” for all the world to see?

Given that, I expect Trump will zip it for the next couple of weeks, though his lack of impulse control might kick in when Michael Cohen takes the stand.

Day Twelve’s first witness was Jeffrey McConney, a portly accountant with a gray mane and goatee who worked for the Trump Organization from 1987 until he retired in 2023, eventually rising to be senior VP and controller.

McConney explained that he and Allen Weisselberg, the former Trump Organization CFO and current resident of Rikers Island (after his conviction for tax fraud), had lunch every day for three decades. By quickly authenticating his old boss’s handwriting (which he said he had seen for 35 years), he spared the prosecution from having to call a handwriting analyst to validate critical evidence.

While McConney had little direct contact with Trump, he told a revealing story about his first year at the company, which Trump also recounts in one of his books. When he reported that the company’s capital balance had gone down after he approved payment to a vendor, Trump summoned him to his office and said, “Jeff, you’re fired.” Trump said he was joking but instructed him that he must never “mindlessly” pay any bill without negotiating the price down. That, as Hillary Clinton noted in a 2016 debate, was Trump’s MO: stiff contractors, bleed them dry with legal expenses if they tried to sue for payment, and settle for 50 cents or less on the dollar. 

“This was a teaching moment,” McConney recalled. It struck me that it was for the jury, too. McConney had inadvertently disclosed that the defendant watched expenditures like a hawk and was, as David Pecker, Hope Hicks, and others testified, a micromanager.

McConney testified that bills were (finally) paid in two ways: From the Donald J. Trump Revocable Trust, which handled payments to the 500 or so entities connected—by ownership, partnership, licensing agreement, and the like—to the Trump Organization; and from Trump’s personal bank account, which Trump alone controlled and wrote checks from. Ten of the 12 reimbursement checks were signed by Trump in the White House and drawn from his personal account. 

Amid all of the mad-boring but critical testimony authenticating the documents, one number stood out for me: $130,000.35. That’s the number Allen Weisselberg scrawled on a bank statement, before “grossing it up” (his words, also scrawled) to $420,000. 

That $130,000 is the same amount the jury now understands was paid from Michael Cohen to Stormy Daniels through her attorney, Keith Davidson. The handwritten evidence proves that the amount was first doubled to $260,000 to make sure Cohen got the $230,000 he was owed after taxes. 

Prosecutor Chris Conroy asked, “Are you aware of any other expenses doubled to account for taxes?

“No,” McConney said, essentially confirming the part of the cover-up that made it seem as if Cohen was being reimbursed for expenses.

Conroy let that sink in for the jury.

The other parts of the “grossing up,” also meticulously recorded in Weisselberg’s hand, were $100,000 for Red Clay, a political consulting firm that Cohen used to gin up phony polls, and a $60,000 bonus for Cohen. 

Cohen wrote on every monthly invoice he sent to Weisselberg and McConney: “Pursuant to the retainer agreement.” McConney confirmed there never was no retainer agreement, though the defense, in its closing argument, will likely point out that Daniels’s attorney, Davidson, admitted that he—like other lawyers—often did business without a written retainer agreement. To further the cover-up, the reimbursements (McConney used that incriminating word) to Cohen were coded “legal expenses” in the Trump Organization’s computerized ledger.

The defense tried and failed to exclude an annual disclosure form that Trump, as president, was required to file with the federal Office of GovernmentEthics (OGE). It seems he might have signed a form that made incriminating misrepresentations, though the testimony about this was so boring that a couple of normally-attentive jurors looked drowsy.

One of the only people in the courtroom who, ironically, seemed fully awake was Trump. He seemed to appreciate that two long-time employees were testifying about how wonderful it was to work for the Trump Organization. Even as the prosecution was cementing its case against him, he appreciated the praise, especially after all of the attacks he endured in the courtroom, with more to come.

On cross, Emil Bove elicited even more praise, but McConney hurt Trump’s case when he admitted that “Most personal legal expenses are not deductible for tax purposes.” Oops. That gives the DA’s office an opening to make tax fraud one of the additional crimes it needs to bring into the case.

The next witness was Deborah Tarasoff, who still serves as the Trump Organization’s accounts payable supervisor. She’s the one who actually cut the checks and brought them to Rhona Graff, Trump’s assistant, to FedEx them to Washington for Trump’s signature. She confirmed that the “accounts payable” and “accounts receivable” stamps were real, and that it was her who initiated the documents..

Zzzzzzzz….

Trump attorney Todd Blanche’s gentle cross mostly consisted of preparing the jury for an argument that during the transition and his early presidency, Trump was too busy to know anything about the real purpose of the checks he was signing. But Tarasoff had almost no contact with Trump, which made her useless to advancing that point.

After court adjourned, the jurors likely went home and told their spouses or friends that they couldn’t talk at all about the trial but it was boring as hell today. They could not share that the foundation of the prosecution’s case was now firmly in place.

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