The New York Times reports that two of the prosecutors heading up the Manhattan District Attorney's Office investigation of former president Trump have resigned.

Mark Pomerantz and Carey R. Dunne, two highly regarded prosecutors, quit the probe after the office's new DA, Alvin Bragg, "indicated to them that he had doubts about moving forward with a case against Mr. Trump," according to the Times.

This is not a surprising development.

The investigation was started by Bragg's predecessor, Cyrus Vance. The probe may initially have been triggered by hush-money payments during the 2016 campaign, made to two women who claimed to have had affairs with Trump years before. Vance also seemed to have been spurred by a mammoth Times report on the history of the Trump real-estate organization, published in 2018. The former DA also fought for a couple of years to get access to Trump's financial records (including tax information), a controversy that went all the way to the Supreme Court twice. Prosecutors were reportedly looking into whether the Trump organization engaged in tax fraud, bank fraud, insurance fraud, and other misconduct. At bottom was said to be the practice of inflating and deflating property values depending on the relevant purpose (e.g., higher value when using them for collateral; lower when paying taxes on them). This practice, we must note, is sufficiently common that New York prosecutors would be extraordinarily busy if they began presuming it criminal; in fact, there are often entirely legal rationales for doing it.

I have great admiration for Pomerantz, who was my Criminal Division chief for a time when I was a federal prosecutor in the Southern District of New York (SDNY). When Vance recruited him, I observed that Pomerantz would not have come on board if a serious investigation were not ongoing. Similarly, Carey Dunne is also a longtime, top-shelf Manhattan litigator.

On the other side of the coin, though, Trump retained the legendary New York defense lawyer Ron Fischetti. Trump's adult children — who ran the business when he was president — have been represented by Alan Futerfas and Marc Mukasey, also Grade-A legal talent. With that kind of firepower on the defense side, prosecutors had better have a strong case if they decide to file charges. To the contrary, all indications have been that this case would be weak.

That was evident, as I explained at the time, from the single indictment that Vance brought in the investigation, against the Trump organization and its chief financial officer, Allen Weisselberg, in July 2021. For all the hullaballoo, the charges were puny — basically corporate perks (cars, apartments, private-school tuition for Weisselberg's grandchildren) for which taxes were allegedly dodged.

Moreover, at around the time Weisselberg was charged, Fischetti said he did not expect Trump to be charged based on his conversations with the prosecutors. Then in November, counsel for Trump organization chief operating officer Matthew Calamari said he'd been informed that the DA's office would not be charging his client, either.

Indeed, we've always gotten more insight into the probe by what hasn't happened than what has.

Recall that Michael Cohen, Trump's self-described "fixer" before the two had an acrimonious falling out, was charged by SDNY prosecutors, and he also provided information to a second federal investigation — that conducted by special counsel Robert Mueller. When Cohen pled guilty in connection with the hush-money payment to Stephanie Clifford (the real name of porn star "Stormy Daniels"), he was obviously trying to score a cooperation agreement with SDNY prosecutors. But he never did; that's why he was sentenced to three years' imprisonment. More tellingly, by summer 2019, the SDNY had closed its investigation of Trump, which the Cohen investigation had prompted.

Now, I worked in the SDNY for nearly 20 years. If there is a juicy, high-profile case to be made, the SDNY makes it — and, if necessary, has been known to steal it from other prosecutors' offices. This is particularly easy to do if there is a turf war between federal and state prosecutors in New York. Ordinarily, the dual-sovereignty doctrine means a state prosecution is not barred by a prior federal prosecution. But New York's constitution has more expansive double-jeopardy protection than the Fifth Amendment does. By filing charges, the feds can "jeopardy out" state prosecutors. That is to say, the SDNY and the FBI never have to step aside for the Manhattan DA and the NYPD; if a case seems desirable, the feds take it.

Michael Cohen was the SDNY's witness, yet its prosecutors wouldn't give him a deal, and they dropped the case. That strongly suggests that it's not much of a case. The Biden Justice Department's id may be anxious to prosecute the Democrats' archnemesis, but its better judgment is to be wary and resist unless there is something truly worth pursuing. Doesn't look like there is.

Four other points.

The Times suggests the main problem for prosecutors has been the "inability thus far to persuade any Trump Organization executives to cooperate." I doubt that. To be sure, no one would expect the former president's children to roll on him, but none of them have been charged either, despite investigators' poring over mounds of their records. And besides not being Trump's children, Weisselberg and Calamari are at an age when serious charges carrying a potentially lengthy prison sentence is usually an irresistible incentive to turn state's evidence. Further, when a case is based on serious financial shenanigans, it is the paper trail that strangles white-collar suspects; with no realistic prospect of acquittal, defendants see the wisdom in becoming cooperators. The issue for prosecutors here is that their investigation hasn't yielded evidence of egregious criminal conduct — as the Weisselberg indictment attests.

Second, New York criminal law is tougher for prosecutors than federal law — there are more protections for defendants, particularly in conspiracy cases. If the feds are unable to make a conspiracy case, chances are the state won't be able to make one.

Third, as we've noted, Alvin Bragg is a progressive prosecutor. He didn't try to fool anyone on that. His policies are nuts, but he ran on them, and Manhattanites elected him (so good luck with that). While progressive prosecutors are known to become aggressive prosecutors when it comes to the banes of progressive existence (e.g., cops), Bragg would look terrible if, while he is declining to prosecute hardened criminals, he appears to go to great lengths to prosecute Trump. That is a headline war with the former president and the New York Post that he does not need in his life unless there is a really strong case to be made. He's clearly not seeing such a case.

Which brings us to the fourth and last point: the state civil-law probe being conducted by Attorney General Letitia James. As the Times notes, James seems to be "escalating" her investigation while Bragg closes shop on the criminal case that hasn't materialized. In a court filing, she claimed to have gathered significant evidence of "fraudulent or misleading" practices engaged in by the Trump organization. And she has gotten a state judge to rule that she can depose Trump under oath. That does not mean she will necessarily get to depose him — Trump is appealing (as are Donald Trump Jr. and Ivanka Trump, whose depositions have also been ordered). In addition, even if they lose their appeals, they could invoke the Fifth Amendment to refuse to answer questions, as Eric Trump did when he submitted to questioning by James's office in October 2020.

It is easier for state attorneys to make a civil case because the burden of proof is less demanding than in criminal cases. But a Trump case might be very tough for AG James. There would be a strong argument that any charge was political rather than evidence-driven because James — whose office is elective, not appointed — campaigned on scorching the earth to nail Trump. Furthermore, as we saw in James's high-profile investigation of former governor Andrew Cuomo, she is known to make provocative allegations that grab the headlines, but then refrain from filing formal accusations that she'd have to prove in court. For all the fanfare of her investigative findings that drove Cuomo from office, not a single case — civil or criminal — was brought based on them.

Like Cuomo, Trump would not go gentle into that good night. If James filed a lawsuit, she'd have a brawl on her hands that would be humiliating if it turned out that her proof did not match her hype.

The former president is not out of the New York woods just yet. But he has a reasonable hope that a clearing has opened before him.