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Are Trump's legal fortunes finally looking up in New York City?

Just when it seemed as if the investigative circle was tightening around Trump, something of a legal bombshell dropped.

Since leaving office, former President Donald Trump has been the target of a series of court cases — almost all of them civil lawsuits filed for a dizzying array of alleged transgressions, from defamation to inciting an insurrection. But one of the most closely watched matters is a criminal case brought by the Manhattan district attorney’s office — a case in which both the Trump Organization and its chief financial officer, Allen Weisselberg, have been indicted for an alleged 15-year-long criminal scheme to defraud in the first degree, among other charges.

The New York prosecution seemed, at least to me, to be moving steadily in the direction of a possible indictment of Trump himself.

The New York prosecution seemed, at least to me, to be moving steadily in the direction of a possible indictment of Trump himself. Trump’s accounting firm, Mazars, recently severed its relationship with the Trump Organization and disavowed the accuracy and reliability of the last 10 years of accounting work it did for Trump. Moreover, as recently as January, The New York Times reported that a number of witnesses had been seen at the site where the Manhattan grand jury convenes, including Trump’s lead accountant and an expert in real estate practices.

In the related civil fraud investigation of Trump and his organization being conducted by New York Attorney General Leticia James, a judge rejected Trump’s attempt to avoid a deposition, ruling that Trump, Don Jr. and Ivanka all must testify. In an eye-popping order, New York Judge Arthur Engoron noted that he had personally reviewed “thousands of documents” that had been subpoenaed as part of James’ investigation, adding that the state attorney general has a right to question Trump under oath when her investigation “uncovers copious evidence of possible financial fraud.”

On Jan. 1, a new district attorney, Alvin Bragg, took over the Trump criminal investigation. But just when it seemed like the investigative circle was tightening around Trump, something of a legal bombshell dropped: The two top prosecutors abruptly and simultaneously resigned from the New York district attorney’s office. Mark Pomerantz and Carey Dunne left behind a case they had been working for years; even more confounding, the Times' reporting suggested they left because the new district attorney “had doubts about moving forward with a case against Trump” himself.

New reporting reveals yet another problematic wrinkle in the saga. The Daily Beast has reported that Bragg is refusing to release the resignation letters submitted by Pomerantz and Dunne, claiming the letters contain “too much information” and could thus compromise an ongoing investigation.

Bragg’s stated reason to decline to release the resignation letters — in whole or in redacted form — rings hollow. Are we to believe that the two prosecutors included intimate investigative details in their resignation letters? Or is it far more likely that Bragg refuses to release them because the letters are deeply critical of Bragg's treatment (and perhaps neglect) of the case?

Bragg’s stated reason to decline to release the resignation letters — in whole or in redacted form — rings hollow.

These are significant, and perhaps ominous, developments. But what we don’t yet know is what it means for the future of the case — presently pending trial — against the Trump Organization and Weisselberg, or for the future of the investigation into Trump himself.

On the one hand, change is inevitable at large prosecutor’s offices. Whether it’s a new district attorney in a state system or a new U.S. attorney in the federal system, any new top prosecutor will inevitably bring different priorities and focus to the mission of the office. Indeed, I worked for 10 different top prosecutors (U.S. attorneys) in my decades at the D.C. U.S. attorney’s office, and each one made changes to our practice. Moreover, sometimes a change in the leadership of an office can result in a fair amount of personnel turnover.

New top prosecutors typically also bring with them new personnel. Indeed, Alvin Bragg brought with him a new executive assistant, Susan Hoffinger, whom he announced will take over as the lead on the Trump matter.

On the other hand, consistency in the staffing of long-term, complex investigations and prosecutions is critically important. Pomarantz and Dunne surely understand the strengths and weaknesses of the collective body of evidence, as well as the nuances and subtleties of that evidence.

On the less tangible front, prosecutors develop important relationships with the witnesses. It’s impossible to overstate the importance of developing trust and respect with these individuals, who may have to appear in a very public trial and testify against the Trump Organization — and potentially even against a former president of the United States.

The district attorney’s office, for its part, has not confirmed speculation that Bragg may be having doubts. A spokesperson for Bragg said the reports that he was not inclined to advance the matter were “not true,” adding that “the investigation remains ongoing and that Ms. Hoffinger will lead the strong team that is in place.”

The natural next question is who is Susan Hoffinger and what qualifies her to take over what The Washington Post described as a 25-person team of prosecutors, paralegals and analysts. Hoffinger joined the Manhattan district attorney’s office in February after 20 years in private practice at a law firm that bears her name, apparently doing criminal/white collar defense work. She does have some prosecutorial experience, having served in the New York DA’s office from 1992 to 2000.

A fair question is whether someone who hasn’t prosecuted a case in 22 years is the right person at the right time to head up one of the most consequential prosecutions in recent New York history. But that’s a question no one can answer — at least not yet.