A federal judge who has become a frequent legal thorn in the side of President Donald Trump and his allies is now presiding over a fight to unseal the warrant used to search the home of Rep. Ilhan Omar, D-Minn.

The battle over whether to unseal the search warrant comes amid two separate federal investigations into the Democratic congresswoman stemming from concerns about discrepancies between financial disclosures filed a year apart and allegations that her father committed fraud when completing immigration paperwork. Omar immigrated to the United States from Somalia in 1995, when she was 12 years old. Investigators are examining whether her father misstated her age on his citizenship paperwork in 2000, potentially allowing her to obtain citizenship through him as a minor.

Trump, a longtime foe of the progressive congresswoman, has been vocal in his attacks against Omar, having also accused her of committing immigration fraud by allegedly marrying her brother — referring to her first husband, Ahmed Nur Said Elmi. In the weeks following the Oct. 12 raid on Omar's Washington, D.C., home, Trump called for Omar to be "put in jail."

But the fight over whether to unseal the records is being overseen by Chief Judge James Boasberg of the U.S. District Court for the District of Columbia, an Obama appointee and longtime target of Trump. In March 2025, after Boasberg temporarily blocked deportation flights carrying alleged Venezuelan gang members, Trump called him a "Radical Left Lunatic of a Judge, a troublemaker and agitator" and called for his impeachment. Trump also accused Boasberg of bias, saying it was "virtually impossible for me to get an Honest Ruling in D.C."

The raid on Omar’s home came just weeks before the midterm elections, as alleged fraud in Minnesota’s social services programs had become a major political issue in the state.

Days after Department of Homeland Security Investigations and the FBI conducted a raid on Omar's home under a search warrant issued by U.S. Magistrate Judge Matthew Sharbaugh, three separate requests were made to unseal the warrant — by the New York Times; Judicial Watch, a conservative watchdog group; and 14 press organizations.

Boasberg ordered the Justice Department to defend its position on keeping the warrant sealed in response to a consolidated request from the Times and 14 press organizations by Oct. 22, but he extended the deadline following a Justice Department request to wait until the search warrant was "fully executed." The Justice Department argued that releasing the information could compromise the integrity of the investigation.

"This request sounds rash because it is rash," Pirro wrote. "The Court should reject it without prejudice for renewal after the search warrant has been fully executed and a charging decision is made public." The filing indicated that the Justice Department was still in the process of executing the search warrant, while other details about the investigation and warrant records remained redacted from the public record.

But the Times and other media groups argue that the physical search occurred weeks ago and that any sensitive information in the warrant should be redacted rather than the entire warrant being withheld.

Meanwhile, Omar is engaged in a separate dispute with the Justice Department. Her attorneys have demanded the return of property seized from her home, arguing that agents violated protections for her congressional work. They have also alleged that agents failed to provide her with a copy of the warrant and prevented her from contacting her attorneys during the search.

Boasberg’s oversight of efforts to unseal the records follows a series of decisions that have drawn criticism from Trump and his allies. In June 2025, he ordered federal agencies to preserve Signal messages exchanged by senior officials while discussing U.S. military strikes in Yemen, saying the communications could constitute federal records. During the Biden administration's Arctic Frost investigation, he signed nondisclosure orders barring phone carriers from notifying Republican lawmakers that prosecutors had subpoenaed their records.

Boasberg also drew criticism over his sentencing of former FBI attorney Kevin Clinesmith. Clinesmith pleaded guilty to altering an email used in an application to the Foreign Intelligence Surveillance Court to renew surveillance of Carter Page, a former Trump campaign adviser suspected of acting as a Russian agent.

Boasberg, who previously served a seven-year term on the FISA Court, said Clinesmith’s alteration of the email undermined the court’s integrity but was a misguided mistake that provided Clinesmith no personal benefit. He sentenced Clinesmith to 12 months of probation and 400 hours of community service.

Boasberg said in his sentencing decision that he believed Clinesmith's role at the center of a years-long media "hurricane" had provided sufficient punishment.