Federal Judge James Boasberg, dubbed a "Radical left lunatic" by President Donald Trump, is presiding over several high-profile cases challenging actions made by the Trump administration, raising questions about how judges are assigned to cases.

The scrutiny comes as Boasberg, an Obama-appointed chief judge of the Washington, D.C. district court, oversees a challenge brought by several media outlets seeking to force the Justice Department to unseal the search warrant on the home of Rep. Ilhan Omar, D-Minn., stemming from two federal investigations.

"Judge James Boasberg is now involved with the Ilhan Omar case," Steve Ferguson, a self-described business owner with more than 250,000 followers on X, wrote in a social media post. "Is everything rigged?" In the federal court of the District of Columbia, cases are assigned to judges randomly by an electronic system managed by the clerk's office operating under the direction of the Calendar and Case Management Committee, according to the rules of the court. The committee consists of three to five judges appointed by the chief justice.

There are exceptions to the random-assignment process. For example, criminal grand jury matters are assigned to and overseen by the chief judge, currently Boasberg. This means Boasberg’s assignment to oversee the fight over unsealing the search warrant for Omar was "not a surprise" to Eric Wessan, Iowa’s solicitor general.

"But there are a lot of cases that seem to be going to judges maybe based on those cases having similarities which is not what the local rules say," Wessan told Fox News Digital.

When a case needs to be reassigned, the Calendar and Case Management Committee will determine how the reassignment is made.

Wessan suggested that concerns over how case assignments are made is valid, considering some of the high-profile cases against the Trump administration which have appeared in Boasberg's docket.

"If one is just following anecdotally, there does seem to be a lot of high-profile cases in front of judges that seem to be expressing unusual amounts of frustration or disagreement with the administration," Wessan said, urging greater transparency in how case assignments are made.

The fight over unsealing the release of Omar's search warrant is just one of several cases involving the Trump administration and now on Boasberg's docket. Boasberg is also overseeing California’s lawsuit against the Trump administration over voter-roll disputes. On Friday, he ordered the administration to provide the state with the names and supporting information for roughly 20,000 people whom the DOJ claims are noncitizens on California’s voter rolls by the end of the day.

Boasberg has issued several consequential rulings against the Trump administration, including a high-profile March 2025 order directing the administration to turn around deportation flights carrying alleged Venezuelan gang members to El Salvador. The Trump administration fought against the order, pointing to the Alien Enemies Act as legal justification for the deportations. The dispute over the administration’s use of the Alien Enemies Act eventually reached the Supreme Court, which vacated Boasberg's temporary restraining order blocking deportation flights, ruling that the case was brought in the wrong jurisdiction.

That same month, Boasberg was assigned a lawsuit seeking to preserve Signal messages after top Trump administration officials discussed plans for a Yemen strike in a group chat that accidentally included Atlantic editor-in-chief Jeffrey Goldberg. He later ordered the administration to preserve the messages.

The string of cases prompted Reps. Jim Jordan, R-Ohio, Darrell Issa, R-Calif., and Chip Roy, R-Texas, to send a letter in May 2025 to the court clerk asking for greater clarity on how judicial assignments are made. The lawmakers questioned whether assignments were truly random, as the court’s rules state.

"The Committee cannot independently verify the randomness of case assignments because the composition of assignment decks is kept secrets," the lawmakers wrote.

"We must understand the nature of the case assignment process in the District Court—which is considering a number of cases challenging the Trump Administration’s policy decisions—to consider and develop appropriate legislation," the lawmakers wrote.

Meanwhile, Sen. Eric Schmitt, R-Mo., introduced legislation in July that would require federal district courts to assign cases randomly, without exceptions, naming it the Boasberg Act. The bill is currently stalled in committee.

"Judge Boasberg is the poster child for a rogue judge and exposed serious loopholes in our judicial system. Randomly assigning cases among judges ensures the American people can have confidence in the impartiality of our courts," Schmitt said in a statement.

Under the rules of D.C. Court, the chief justice does not have the power to reassign a case. The Calendar and Case Management Committee handles case reassignments. The court must notify the judges and attorneys involved, but it does not have to publicly explain why a case was reassigned. Wessan has called for greater transparency.

"The rules shouldn’t say one thing if it’s not true. But if it is true, they could just say so. I think the issue is with the exceptions—what happens in those exceptional cases and how often do they occur?" Wessan said.

"Given the frequency of the concerning episodes in the district court, erring on the side of transparency is probably prudent to the extent that there are exceptions to the normal random-assignment system," Wessan said.