A judge has thrown out two of their most high-profile indictments.
Grand juries have repeatedly refused to charge those they are targeting.
And now, in the wake of a lacerating ruling by a federal judge derailing an inquiry into the Federal Reserve chair, Jerome H. Powell, officials at the Justice Department have encountered an even more profound problem: Prosecutors are floundering in the most basic steps of criminal investigations into those President Trump wants scrutinized.
The latest setback in the president’s retribution campaign came on Friday when Judge James E. Boasberg of Federal District Court in Washington quashed grand jury subpoenas to the central bank for information about the renovations underway at its headquarters and Mr. Powell’s testimony to Congress about them.
The U.S. attorney overseeing the case, Mr. Trump’s longtime friend and ally Jeanine Pirro, has vowed to appeal the decision and cast Judge Boasberg, who has clashed with the Trump administration, as an activist. And an appeals court could ultimately overturn the decision.
Still, Judge Boasberg’s ruling was an extraordinary example of pushback by the judicial branch, cutting short the investigative process at an exceptionally early stage, when prosecutors are essentially doing the most basic work of federal law enforcement.
Last fall, after Mr. Trump demanded his political appointees ratchet up his retribution campaign, the Justice Department ran into roadblocks once a judge tossed out indictments against the former F.B.I. director, James B. Comey, and the New York attorney general, Letitia James. The prosecutor who brought the charges, the judge declared, had been appointed illegally.
Then, in February, a grand jury in Washington refused to indict six Democratic lawmakers whom Mr. Trump wanted prosecuted for sedition after they released a video reminding military and intelligence personnel of their obligation not to obey illegal orders.
But Judge Boasberg’s block on the subpoenas against the Federal Reserve was in some ways an even sharper rebuke, stopping prosecutors in their tracks at the fact-gathering stage of their investigation after determining that it was flawed from the outset. The move proved again that even though Mr. Trump has long claimed nearly boundless powers to use the law as a cudgel against his foes, he does not exercise full or unilateral control over the legal system.
As a general rule, prosecutors are given great leeway in issuing grand jury subpoenas, a common tool in the early stages of investigations. Unlike search warrants, they do not require a finding of probable cause by a judge that there might be evidence a crime was committed.
But Judge Boasberg found that Ms. Pirro’s office did not even meet the extremely low threshold needed to send the subpoenas, ruling there was “essentially zero evidence to suspect Chair Powell of a crime.”
Instead, the judge surmised, the real reason the subpoenas were issued was political: because Mr. Trump wanted to strong-arm Mr. Powell into lowering interest rates.
“The subpoenas’ dominant (if not sole) purpose is to harass and pressure Powell either to yield to the president,” Judge Boasberg wrote, “or to resign and make way for a Fed chair who will.”
Judge Boasberg explicitly acknowledged the reality of Mr. Trump’s revenge campaign, writing that the president had urged the Justice Department to investigate his adversaries and adding that the department’s prosecutors had listened. In and of itself, it was an extraordinary acknowledgment. Citing a Supreme Court case, he wrote that “judges ‘are not required to exhibit a naïveté from which ordinary citizens are free.’”
The Federal Reserve subpoenas were not the only ones associated with Mr. Trump’s revenge campaign to have been dealt a blow last week. A New York judge, Lorna G. Schofield, refused to pause her own order blocking Justice Department subpoenas related to an attempted civil rights investigation into the New York attorney general, Ms. James. Judge Schofield said that the U.S. attorney who sent the subpoenas, John A. Sarcone III of the Northern District of New York, had remained in his position unlawfully, invalidating the inquiry into Ms. James.
When Mr. Trump began his second term, he was determined to use his expansive powers over the department to go after his rivals, subjecting them to the same legal ordeal that he believed he had unfairly undergone when he was out of office.
He wanted indictments, trials, guilty verdicts and ultimately jail for his enemies.
But the cases he has demanded in recent months have become so far removed from justifiable prosecution that even the loyalists he has installed have found it difficult to push them through a judicial system that does not appear to have hesitated to push back.
As remarkable as Judge Boasberg’s ruling was, it reflected a broader trend of judges across the country who increasingly doubt the word of lawyers for the Justice Department. Those lawyers have traditionally enjoyed a solid bond of trust with courts known in legal parlance as the presumption of regularity.
But that presumption has eroded over the past year. Several department lawyers have resigned in protest over Mr. Trump’s efforts at retribution, and some who have remained have been held in contempt for violating dozens of orders or been suspected of filing vindictive charges against people who have run afoul of Mr. Trump.
Over and over, prosecutors have been caught between the rock of the president’s insistence that they undertake weak or baseless cases and the hard place of having to go to court to push those cases past the justice system’s institutional guardrails. The experience has so rattled some people in Ms. Pirro’s office in particular that they have shelved some investigations determined to be weak rather than present them to grand juries and face the prospect of being rejected yet again.
Still, amid all of these setbacks, Judge Boasberg’s ruling on Friday represented a different, and more pointed, form of failure. As the chief judge in Federal District Court in Washington, Judge Boasberg oversees all legal disputes arising from grand juries. He could stand to thwart any further moves by Ms. Pirro’s office to use grand juries in dubious or baseless investigations of Mr. Trump’s adversaries for conduct that occurred in Washington.
Ms. Pirro cast Judge Boasberg’s decision as potentially having an impact on other criminal cases, acknowledging at a news conference on Friday that the judge had opened the door for “other defense attorneys around the country” to make similar arguments, making it harder on prosecutors to investigate.
And Judge Boasberg’s decision, while rare, is unlikely to be the last time a federal jurist decides the fate of grand jury subpoenas used in an inquiry of Mr. Trump’s political adversaries. A federal judge in Minnesota is working behind closed doors to consider a request to quash subpoenas issued in January as part of an investigation into whether a group of elected Democrats — including Gov. Tim Walz and Jacob Frey, the mayor of Minneapolis — conspired to impede thousands of federal agents sent to the state as part of the administration’s immigration crackdown.
Mr. Trump’s retribution campaign began after he took office with great momentum, with law firms and universities falling into line as he used his power to force them to capitulate. But once he turned his attention to the criminal justice system, his efforts to use it for retribution ran into major obstacles.
In November, a judge threw out the indictments filed against Mr. Comey and Ms. James after determining that an inexperienced loyalist, Lindsey Halligan, whom Mr. Trump had personally picked to bring the charges, had been illegally appointed to her job as the U.S. attorney for the Eastern District of Virginia.
Weeks later, prosecutors in Ms. Halligan’s office stumbled yet again in their efforts to charge Ms. James. Two grand juries — one in Norfolk, Va., and another in Alexandria — refused in quick succession to bring a fresh indictment in the case. Grand juries declining to bring charges was once the rarest of legal rarities, but it has become an increasingly common experience for the Justice Department under Mr. Trump.
Indeed, last month another grand jury, in Washington, threw another wrench into the president’s revenge tour. The ordinary citizens on the panel rejected efforts by Ms. Pirro’s office to seek an indictment against the six Democratic lawmakers who posted the video addressing military members.
And rather than face the humiliation of being rebuffed yet again, Ms. Pirro’s prosecutors appear to have quietly set aside an inquiry into whether former President Joseph R. Biden Jr. and his aides had violated the law by using an autopen to sign presidential documents. Despite fierce pressure from Mr. Trump to make a case against Mr. Biden, prosecutors failed to determine what, if any, laws may have been broken.
After The New York Times reported in March that the investigation had been shelved, Ms. Pirro publicly suggested that the case may be continuing.
Jonah E. Bromwich contributed reporting.
Michael S. Schmidt is an investigative reporter for The Times covering Washington. His work focuses on tracking and explaining high-profile federal investigations.
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