Here’s a lesson learned over the past year. Don’t underestimate New York County District Attorney Alvin Bragg Jr., a self-described “son of Harlem” and a Harvard Law School graduate. Donald Trump certainly did, but so did many progressives.
Let’s flash back to a year ago: In March 2022, Manhattan’s first Black district attorney was getting pummeled after he refused to bring charges against Donald Trump for financial crimes. In late 2021, Bragg’s predecessor, Cyrus Vance Jr., tasked Mark Pomerantz, a former federal prosecutor, and his general counsel, Carey Dunne, with investigating Trump and his businesses for tax fraud. Pomerantz’s team then began subpoenaing witnesses and presenting evidence to a grand jury. Vance had been convinced to proceed toward an indictment but left the final decision to his successor.
Bragg took office in January 2022, but a month later, he declined to seek criminal charges against Trump and suspended presenting evidence to the grand jury. I was surprised initially by Bragg’s decision. As a Manhattan resident, I had voted for him in a highly competitive Democratic primary in June 2021.
That was based on Bragg’s track record as a top deputy to New York State Attorney General Letitia James. He oversaw the civil lawsuit that led to the dissolution of the Donald J. Trump Foundation for such improper activities as using funds to pay off Trump’s legal obligations and providing extensive support to his 2016 presidential campaign.
And then, on March 23, 2022, The New York Times published the text of Pomerantz’s resignation letter.
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Pomerantz wrote that his team ”harbors no doubt” about whether Trump committed crimes. He wrote:
”His financial statements were false, and he has a long history of fabricating information relating to his personal finances and lying about his assets to banks, the national media, counterparties, and many others, including the American people.”
And he added:
“I believe that your decision not to prosecute Donald Trump now, and on the existing record, is misguided and completely contrary to the public interest. I therefore cannot continue in my current position.”
A Trump lawyer, Ronald P. Fischetti, issued a statement applauding Bragg “for adhering to the rule of law and sticking to the evidence while making an apolitical charging decision based solely on the lack of evidence and nothing else.”
One of Bragg’s primary rivals, Eliza Orlins, a public defender, declared, “It’s business as usual at the Manhattan DA’s office—failure to hold the powerful to account while preying on the most vulnerable New Yorkers,” The Daily Beast reported.
All the criticism
MSNBC legal analyst Glenn Kirschner, in his Justice Matters podcast, said Pomerantz’s letter “in a very real sense is an indictment of District Attorney Alvin Bragg.” Kirschner added that “there are times when prosecutors abuse their prosecutorial discretion,” calling Bragg’s decision “more befitting” of Trump’s Attorney General Bill Barr.
And there were even withering comments about Bragg from some members of the DK community. There were suggestions that Bragg was getting money from Russia, Trump, or the Koch brothers; he was being threatened by the Russian mob; he was spineless, corrupt or simply incompetent, and that he should be investigated and removed from office.
The general consensus a year ago was that the Manhattan district attorney’s probe of Trump was dead in the water, even though Bragg’s spokeswoman, Danielle Filson, said that the Trump investigation was continuing. She added: “A team of experienced prosecutors is working every day to follow the facts and the law. There is nothing more we can or should say at this juncture about an ongoing investigation.”
The New York Times reported that Bragg’s decision not to pursue the case developed by Pomerantz a year ago was based on memos from a career prosecutor in his office, Chris Conroy, highlighting potential gaps in the evidence.
The Times said Bragg had “developed concerns” about relying on the testimony of Michael Cohen, Trump’s former lawyer and fixer, “questioning whether he had enough knowledge about the intricacies of Mr. Trump’s financial records to be a pivotal witness.” The prosecutors lacked a corroborating witness from inside the senior ranks of the Trump Organization.
“not a slam dunk”
Even Pomerantz admitted in his book, “People vs. Donald Trump: An Inside Account,” published in February, that his case against Trump “could not be described as a slam dunk,” The Daily Beast reported. The key issue of contention was whether prosecutors could prove that Trump knowingly falsified the value of his assets on financial statements to defraud bank lenders and tax assessors when disclosing the value of various holdings to secure high-value loans. Trump’s penchant for exaggerating his wealth posed an obstacle for prosecutors trying to prove criminal intent.
But it turned out that people underestimated Bragg. His office has done a lot over the past year to hold powerful people close to Trump accountable. In September, Bragg’s office indicted right-wing provocateur Steve Bannon on state-level money laundering, fraud, and conspiracy charges related to his We Build The Wall foundation. A federal case stemming from much of the same alleged conduct was cut short when Trump pardoned Bannon shortly before leaving office.
In August, Allen Weisselberg, the former CFO of the Trump Organization, pleaded guilty to evading taxes on a free apartment and other perks he received from the company amounting to about $1.7 million. In a plea deal, the 75-year-old Weisselberg agreed to testify against the Trump Organization at a trial and was sentenced to serve five months in New York City’s Rikers Island prison complex.
In December, Judge Juan M. Merchan imposed a $1.6 million fine on the Trump Organization after Bragg’s prosecutors secured a conviction a month earlier on charges including conspiracy, criminal tax fraud, and falsifying business records in a scheme that enabled Weisselberg and other top executives to evade taxes on perks received from the company. Merchan, who also handled the Weisselberg sentencing, will preside over Trump’s arraignment on Tuesday.
building the case
And quietly, without much fanfare, Bragg’s office began to build the case that led to last week’s indictment of Trump. That indictment was filed by Conroy, the same prosecutor who had cast doubts on pursuing the case developed by Pomerantz, the Times reported.
In a lengthy account of how Bragg resurrected the case against Trump, the Times described how Bragg’s team dug into the numerous files gathered over the years by Vance’s office, including those relating to the 2016 hush money deal with Stormy Daniels, who claimed she had a sexual relationship with Trump. Vance had turned his focus to the asset valuation fraud case, but the hush-money inquiry never died and became known as the “zombie case” because it kept coming back to life. Cohen was a more reliable witness in this case because he was directly involved in making the $130,000 payment to the porn star, and then got reimbursed by Trump.
In July, according to the Times, Bragg began building up a team of prosecutors to develop the case. Then in December, as the trial of the Trump Organization was wrapping up, Bragg’s office hired Matthew Colangelo, a former senior Justice Department official, to help lead the Trump hush money inquiry. Colangelo had previously worked with Bragg in the New York State Attorney General’s office, developing the civil case against the Trump Foundation.
In January 2023, Bragg’s office began presenting evidence to a newly empaneled grand jury about Trump’s role in the hush money case. Cohen was the key witness, but the grand jury also heard testimony from others—David Pecker, the former publisher of The National Enquirer who helped arrange the payoff to Daniels, as well as Trump employees and campaign aides, including Kellyanne Conway and Hope Hicks.
And Trump ended up underestimating Bragg. After Trump ally, lawyer Robert Costello, appeared on March 20 as a rebuttal witness before the grand jury to challenge Cohen’s credibility, Trump expressed optimism that he would be spared from indictment.
In a post on his Truth Social platform, Trump wrote:
"It is being said that disbarred lawyer Michael Cohen was put out to dry today after his highly respected former attorney and legal adviser, Robert Costello, made a great impression not only on the D.A.'s Office, but the grand jury itself."
"He is known to be a great lawyer and highly honorable man. He stated to the media that he could no longer listen to the lies that Cohen was spreading. He told the TRUTH, with papers, documents, and backup. He left ZERO doubt. THE D.A. WILL DO THE RIGHT THING!"
Ten days later, Trump was charged with more than 30 counts in a sealed indictment whose contents should be revealed on Tuesday when the former president is expected to be arraigned. No one knows whether the charges might go beyond the Stormy Daniels hush money case.
the big unknown
But that didn’t stop many pundits from opining that the first indictment of a former U.S. president was basically a weak case. A Washington Post editorial described the indictment as “a poor test case for prosecuting a former president.” Could this be another instance of underestimating Bragg?
And finally there’s a big unknown—Trump’s trial is not expected to begin until next year, and a lot could happen before then to impact the landscape. Fulton County District Attorney Fani Willis could indict Trump for attempting to interfere in the 2020 presidential election in Georgia. And Justice Department special counsel Jack Smith could bring charges against Trump based on separate investigations into Trump’s handling of classified documents at his Mar-a-Lago estate and his attempts to overturn the results of the 2020 election.
In New York, Attorney General Letitia James’ civil fraud lawsuit against Trump, three of his adult children, and their family business is now scheduled to begin on Oct. 2. The $250 million lawsuit concerns Trump’s alleged efforts to manipulate asset valuations to gain better terms from banks and insurers.
That trial could prove embarrassing to Trump, who repeatedly took the Fifth Amendment when asked about his business practices in a deposition. The lawsuit also seeks to bar the Trumps from running a business in New York. The civil case largely overlaps the criminal case developed by Pomerantz. Could a guilty verdict encourage Bragg to revive the case he got pummeled for declining to pursue a year ago?
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