It’s rare for grand juries to refuse to indict. It’s even rarer for grand juries to refuse to indict multiple times in a single month—in significant part because prosecutors usually know better than to present shaky cases that might not gain jurors’ approval.But Donald Trump’s desire to crack down on crime in Washington, D.C., seems to have come at the cost of that good judgment. Over the past month, federal prosecutors in D.C. have failed at least five times to persuade a grand jury to indict a D.C. resident for allegedly attacking federal law enforcement. These are not the only embarrassments suffered recently by federal prosecutors in the District, and judges have begun to lose their patience over missteps and sloppy cases. Despite the president’s promise to “take our capital back,” his law-enforcement surge is struggling in court.The most recent rebuke by a grand jury involves the case of Alvin Summers, who allegedly scuffled with a U.S. Park Police officer after driving his car onto the Mall. Before that came a grand jury’s refusal to indict Sean Charles Dunn, the man now memorialized as “Sandwich Guy,” who hurled a salami sub at a Customs and Border Protection agent early in Trump’s federal deployment across the capital. The three grand-jury refusals before that all came in a single case: that of Sidney Lori Reid, whom prosecutors charged with a felony—potentially punishable by eight years in prison—over a tangle with FBI and ICE agents while Reid was protesting an immigration arrest. The agents pushed Reid up against a wall, they said, and the resulting scuffle produced a few scrapes to an FBI agent’s hand.Trump formally announced his crackdown on August 11, claiming an emergency need to put an end to violent crime that was in fact already at a 30-year low. In the intervening weeks, federal law-enforcement officers from a range of agencies have patrolled the city’s streets alongside the National Guard and the Metropolitan Police Department, itself newly under presidential direction. The White House has produced some impressive-sounding statistics to justify the surge, pointing to more than 1,000 arrests since early August. The U.S. Attorney’s Office for the District of Columbia, meanwhile, is filing cases in federal court at a rapid clip. Whereas the office would normally submit a case or so daily, last week it filed 14 in a single day—a rate comparable to the early January 6 prosecutions, when prosecutors were charging rioters by the dozen. According to CNN, prosecutors are filing about 100 cases a day in D.C. Superior Court, roughly double what the local court sees in normal times.The strength of these cases, however, is a different question. Summers, Dunn, and Reid are three of the almost 20 people charged with “assaulting, resisting, or impeding” a federal officer in the course of the D.C. deployment. The charge can be a misdemeanor, but in most—and possibly all—of the cases filed since early August, prosecutors have pursued a felony instead. This is consistent with U.S. Attorney Jeanine Pirro’s orders to her office to charge defendants with the harshest penalty available and to do so in federal court, where punishments are stiffer. Christian Enrique Carías Torres, a Venezuelan delivery driver, was charged with a felony after struggling during a violent arrest by masked immigration authorities. At least three other felony cases involve allegations that defendants spat on federal law enforcement or members of the National Guard.[Ashley Parker and Nancy A. Youssef: Why is the National Guard in D.C.? Even they don’t know.]The alleged spitting incidents were seemingly motivated by the disgust many D.C. residents feel toward what Trump is doing to the city. Other cases resulted from sending out federal officers, many of whom are highly trained in elite specialties, to work as beat cops. One man is now facing felony charges after law enforcement found him sitting in his car with a cup of “green liquid” that smelled “consistent with alcohol”—normally a misdemeanor violation of open-container regulations under local D.C. law—because he kicked agents from Homeland Security Investigations and the Diplomatic Security Services while they were arresting him.Filing federal-felony charges against someone starts a ticking clock. Prosecutors have 30 days to secure an indictment from a grand jury, and the refusal of jurors to indict Summers, Dunn, and Reid might suggest more trouble ahead for other cases yet to reach this stage. Grand jurors can decline to indict because they don’t believe the government has adequately made its case; they can also decline simply because they don’t like or trust the prosecutor and don’t agree with what the government is trying to do. Despite its reputation as a rubber stamp, this is the core democratic promise of the grand jury, and its power in the face of government overreach.The Trump administration has already run into this problem elsewhere: Following this summer’s demonstrations in Los Angeles, prosecutors in the Central District of California have struggled to secure indictments of anti-ICE protesters before skeptical grand juries. But the D.C. situation presents an additional complication. Unlike the sprawling and politically diverse region around L.A., the District of Columbia has only 700,000 residents, less than 7 percent of whom voted for Trump in 2024. Trump’s deployment in the city is hugely unpopular, and the city’s small size—only 68 square miles—is such that most D.C. residents have probably brushed up against the law-enforcement surge in one form or another. This is the pool of potential grand jurors prosecutors will have to persuade to indict. And if any of these cases go to trial, this pool will also provide the jurors who will choose whether to convict.And grand jurors are not the only people in D.C.’s federal courthouse who are losing their patience with Trump’s crackdown. Also less than pleased are magistrate judges, the workhorses who assist Senate-confirmed district judges with managing the court’s workload. “The time and resources of the court are stretched beyond belief,” Magistrate Judge Moxila Upadhyaya commented during a hearing. After one defendant was detained unnecessarily for days, Magistrate Judge Zia Faruqui lambasted the government for its “inexcusable” and “egregious” delay.Faruqui likewise appeared frustrated when prosecutors arrived in court asking to dismiss a gun charge they had filed only days before. “We don’t just charge people criminally and then say, ‘Oops, my bad,’ Faruqui chastised the government. According to The New York Times, prosecutors moved to dismiss the case over concerns that the police search that uncovered the gun may have been illegal. That risked a problem for the government that could go well beyond this specific case—say, if an appeals court were to review the search and establish precedent limiting searches even further.When Carías Torres, the delivery driver, appeared before Faruqui, the magistrate judge ordered him released from pretrial custody—saying, “You should be treated with basic human dignity. We don’t have a secret police.” But as Faruqui acknowledged, Carías Torres’s freedom may be short-lived if ICE takes him into custody for immigration proceedings—a reminder that the criminal and immigration elements of the federal presence in D.C. run on separate tracks. Even as federal criminal cases flounder, the escalation of immigration enforcement in the city—which the White House says accounted for 40 percent of arrests conducted during the first week of the federal surge—has pushed onward with grinding effectiveness.[Quinta Jurecic: Trump’s farcical D.C. crackdown]Typically, courts are reluctant to lift the veil of grand-jury secrecy. In most cases, defendants themselves don’t even know that a grand jury has declined to indict until prosecutors drop charges or otherwise give a signal. But magistrate judges have shown their discontent by taking the unusual step of alerting Summers’s and Reid’s defense lawyers that grand juries declined to indict their clients. Prosecutors may have received the message: In all three cases where they’ve failed to secure indictments, they appear to have finally given up rather than trying once again. For Summers, they filed a motion to toss the case altogether. For the Sandwich Guy, they’ve opted instead to charge him with a lesser misdemeanor, for which a grand jury is not required.The government chose to file a misdemeanor against Reid as well. On Thursday, I stopped by the federal courthouse for her arraignment. She pleaded not guilty and requested a jury trial. The parties should be prepared for jury selection to take longer than usual “given the current environment,” the judge noted. At another point, prosecutors appeared confused when Reid’s lawyers raised concerns over belligerent social-media posts by ICE attacking Reid after her arrest.Apart from those exchanges, the hearing provided little indication that anything out of the ordinary was going on. Outside, it was a crisp late-summer day, with no particular signs of chaos or violent disorder. Tourists and young professionals walked along Constitution Avenue. The only sign of Trump’s deployment was a lone member of the National Guard standing in a nearby Metro station, staring at a vending machine for transit cards as if wondering how to pay his fare.