The Manhattan Trump Criminal Investigation: The Saga of Mark Pomerantz & Alvin Bragg

Former prosecutor Mark Pomerantz, who quit the Manhattan DA’s office last year in a huff over how the newly elected District Attorney Alvin Bragg was conducting the Trump criminal investigation, has written a tell-all book.

A timeline will lay out the progress of the investigation and offer a context for the Pomerantz-Bragg saga:

August 2019: Manhattan D.A. Cyrus Vance kicked off the Trump criminal investigation when he subpoenaed the Trump Organization and Trump’s accounting firm, demanding eight years of Mr. Trump’s personal and corporate tax returns.

September 2019: Trump sued to keep his tax returns secret.

July 7, 2020 and February 2021: Vance’s case went to the U.S. Supreme Court where, both times, he scored victories: In July, the Court held that Trump does not have an absolute right to block the release of his tax returns and in February, blocked his final bid to protect his returns.

February 22, 2021: Trump’s tax returns were turned over to Vance’s office.

May 28, 2021: Mark Pomeranz was recruited to work on the investigation, specifically to “help scrutinize financial dealing” at Trump’s company.

July 1, 2021: Vance indicted The Trump Organization, the Trump Payroll Organization, and Trump Org CFO Allan Weisselberg in what prosecutors called  “a sweeping and audacious” tax fraud scheme.

Fall 2021: NY Investigators issued new subpoenas for information about Trump’s properties.

November 2021: The Manhattan DA’s office convened a grand jury to hear evidence.

January 1, 2022: Alvin Bragg took office as the new DA.

February 2022: New York prosecutors were unable to persuade any Trump Organization executives to cooperate and turn on Mr. Trump.

I interrupt this timeline to bring you lessons from The Godfather

This is from The Godfather, pages 41-42:

That Sunday morning, Don Corleone [the Godfather] gave explicit instructions on what should be done to the two young men who had beaten the daughter of Amerigo Bonasera. But he had given these orders in private to Tom Hagen [the Consigliere.] Later in the day Hagen had, also in private without witnesses, instructed Clemenza. In turn Clemenza had told Paulie Gatto to execute the commission.”

The advantage of giving orders in private without witnesses is explained:

Each link of the chain would have to turn traitor for the Don to be involved and though it had never yet happened, there was always the possibility. The cure for that possibility was also known. Only one link in the chain had to disappear.

Prosecuting Trump becomes difficult if people just under him, the top-level Trump Organization executives who spent a lifetime getting rich while helping Trump cheat, are willing to take the fall for him. Imagine the Chief Financial Officer telling the jury, “Most of this stuff Trump didn’t even know about, and the stuff he did know about, I had assured him that it was legal, and because I am an accountant, he believed me.”

A jury might convict despite such testimony, but given the extraordinarily high standards in a criminal trial—to convict, the jury must find the defendant guilty beyond a reasonable doubt—it seems just as likely that a jury would acquit Trump and convict Weisselberg.

When stories came out that Allen Weisselberg was refusing to flip on Trump, my guess was that Weisselberg figured that he and his family had lived a life of luxury so he owed it to Trump to go to prison for him.

Okay, back to the timeline.

 February 23, 2022, Mark Pomerantz resigned from the Manhattan District Attorney’s Office in a huff. According to headlines and reporting “Prosecutors in Trump probe quit after new DA [Bragg] seems to abandon the plan to seek an indictment of the former president.”

One person familiar with the situation  (most likely Pomerantz leaking to the press) said Bragg “took weeks to read memos Dunne and Pomerantz had prepared and didn’t meet with them for some time, even though the grand jury’s term was set to expire this spring. When they did meet, Bragg didn’t seem keenly interested.”

In other words, Bragg was portrayed as slow-moving and lazy, taking weeks to read memos, disinterested, and seemingly unaware of deadlines.

Alvin Bragg confirmed that Pomerantz and Dunne resigned, but he would not comment. He also said the criminal probe was “ongoing.”

Left-Leaning Social Media had a Meltdown

I am including screenshots to show you the level of engagement these responses received:

The idea was that the case was a slam dunk and Bragg was too timid to move forward.

I felt skeptical. My response: “I don’t know much about Bragg, but I know prosecutors tend not to get cold feet when the case is a slam dunk.” My conclusion at the time was that most likely, there was a difference of opinion about the strength of the case and the best way to move forward.

Notice how much less engagement a response like mine gets from rage-inducing headlines (under 400 “likes” as opposed to more than 5,000. There. I got that off my chest.)

The plot thickened when senior officials in the DA’s office came to believe Pomerantz had selectively and misleadingly leaked information to the press, including his resignation letter, in order to damage Bragg. (Leaking stuff to the press during an ongoing investigation is a firing offense. Leaking stuff to the press after leaving a DA’s office where the person was privy to details about an investigation is potentially damaging to the investigation and unethical.)

August 18, 2022: Weisselberg pleaded guilty but it still appeared he would not implicate the Trump family.

December 6, 2022: The Trump Organization was found guilty on all counts of criminal tax fraud.

January 10, 2023: Weisselberg was sentenced to 5 months in Rikers (a notoriously horrible place). The reduced sentence was because he pleaded guilty as part of a deal.

Read about Rikers here. If you want to read more, Google “violence at Rikers.” One observer said Rikers resembles a “slave ship.”

January 13, 2023: Bragg tells CNN that his office’s investigation is continuing.

January 18, 2023: The media reported that Bragg appeared to have “changed his mind” about investigating Trump, which assumes that he had previously made up his mind not to investigate Trump, an assumption which came from Pomerantz.

In January there were rumors that Bragg was going after the Trump-Michael Cohen-Stormy Daniels hush money payoff scheme and that he was again looking at Weisselberg.

Question: After 5 months at Rikers, will Weisselberg feel differently about pleading guilty and taking the fall for Trump?

January 30, 2023: We learned that Bragg’s office was presenting the Trump case to a grand jury.

February 6, 2023: Mark Pomerantz published an insider’s “tell all” book called People vs. Donald Trump slamming Bragg’s office. In other words, after quitting, he not only leaked stuff to the press, he ran off to get a book deal. (Don’t worry. I didn’t buy his book.)

Here is the description on Amazon:

People vs. Donald Trump is a fascinating inside account of the attempt to prosecute former president Donald Trump, written by one of the lawyers who worked on the case and resigned in protest when Manhattan’s district attorney refused to act.

Bragg responded by saying, “I bring hard cases when they are ready.”

NYU law professor Ryan Goodman, writing for Just Security, pointed out that there were discrepances between Pomerantz’s book and his own resignation letter, and that parts of Pomerantz’s story were highly improbable

For example, Pomerantz’s resignation letter stated that Vance had directed the DA’s office to seek an indictment, but Bragg decided to effectively drop the case. In fact, Pomerantz’s book (and this interview with Ari Melber) contradict this narrative. It’s also unlikely that Vance would issue a directive to his successor.

Moreover, as late as December 9, 2021, Pomerantz and Dunne changed their theory of the case from “scheme to defraud” to “falsification of business records” because such a charge would not require proof of financial loss.

Pro tip: If you are changing the theory of the case in December, you are not yet ready to indict in January.

If you can stomach listening to Pomerantz talk, you can watch Ari Melber take him apart here. Among the notable moments was Pomerantz basically admitting that part of his motive in wanting to indict was that Trump had been calling him names. Melber said, “So this is personal?” (Pro tip: Indictments are not supposed to be personal.)

There are two kinds of prosecutors. (I suppose there are also two kinds of defense lawyers: Those who divide prosecutors into two kinds and those who don’t 😂)

(1) The careful meticulous prosecutor builds a strong case and makes sure that he or she is bringing indictments for the right reasons.

(2) The emotional, impulsive, “I’m a tough guy” prosecutor who cannot be reasoned with and who equates meticulous care with weakness. This kind of prosecutor tends to engage in all-or-nothing thinking, speak in platitudes about justice*, and rely on emotional appeals.

*I started to tell a story about a prosecutor I dealt with who kept giving me platitudes with words like “justice” and “pay the price,” but maybe another time.

(Unfortunately, in a click-driven media environment, the second type is often invited to be TV commentators.)

Several Black civil rights leaders felt offended by what they saw as racial undertones in Pomerantz’s attack on Bragg. They pointed out that throughout his book, Pomerantz implied that Bragg was disengaged, lazy, and not qualified, thereby describing Bragg with “tired racial tropes to undermine and disparage” the first elected Black Manhattan District Attorney.

They  also pointed to an email that Pomerantz wrote to Bragg essentially telling Bragg, “You need to respect our judgment.” (In other words, You need to respect me.) Bragg was a highly experienced prosecutor, elected by the voters, and in charge of the office. These leaders suggest that Pomerantz would not have used such a tone with any of Bragg’s predecessors.

Will Alvin Bragg bring charges? I don’t know and neither does anyone else. Bragg and those close to him probably have a good sense of whether an indictment will come out of this, but they’re not telling.

We will just have to wait and see.

The lesson: Don’t believe leaks about ongoing criminal investigations.

If you’re new to my blog, and you feel inclined to leave an angry or cynical comment, I suggest reading this page first.