Venezuelan man suing over illegal deportation to CECOT and ensuing 'torture' draws the judge Trump probably hates the most

A Venezuelan man suing the federal government over an illegal deportation leading to prolonged "torture" in a foreign prison may find himself before one of the president's most prominent judicial foils.

On Thursday, the U.S. District Court for the District of Columbia took up the case stylized as Rengel v. United States, a Federal Tort Claims Act (FTCA) lawsuit seeking some $1.3 million in damages. The plaintiff, Neiyerver Adrián Leon Rengel, is suing the government over his deportation and the ensuing torture he says he suffered in the El Salvadoran prison known as the Center for Terrorism Confinement (CECOT).

In typical fashion, the case was assigned to a judge through the district's randomized selection process. That process may have resulted in a boon for the plaintiff in the first-of-its-kind case.

Through the use of a multi-layered "assignment deck" within a broader "automated system," Chief U.S. District Judge James Boasberg, a Barack Obama appointee, was handed the reins in the novel litigation.

When assigning civil or criminal cases to federal judges, there is no general process observed throughout the country. Instead, judicial selection is typically handled by each court at the local level — and explained via published rules or a standing order. Initial case assignment, however, is usually made to achieve a random result.

In the District of Columbia, the general assignment rule is that "cases shall be assigned to judges of this Court selected at random."

The district court's rules explain, in relevant part:

(1) The Clerk shall create a separate assignment deck in the automated system for each subclassification of civil and criminal cases established by the Court…The decks will be created by the Liaison to the Calendar and Case Management Committee or the Liaison's backup and access to this function shall be restricted to these individuals to protect the integrity and confidentiality of the random assignment of cases. The Calendar and Case Management Committee will, from time to time determine and indicate by order the frequency with which each judge's name shall appear in each designated deck, to effectuate an even distribution of cases among the active judges.(2) At the time a civil complaint is filed or an indictment or information is returned in a criminal case, the case shall be assigned to the judge whose name appears on the screen when the appropriate deck is selected…

"All proceedings in a case after its assignment shall be conducted by the judge to whom the case is assigned, except as otherwise provided," the rules go on, referring to reassignments and transfers. And, the rules note, moving a case from one judge to another is far more likely – or at least far more accounted for – in the criminal realm.

The upshot of Boasberg taking the case is that he will almost certainly remain at the helm of the first-of-its-kind lawsuit.

And Boasberg is not one of President Donald Trump's favorite judges. In fact, through most of last year, Boasberg was arguably the judge the 45th and 47th president targeted the most with vitriol, antipathy, and demands he be pulled from the bench.

The district judge was targeted by the Trump administration for repeatedly ruling against the government in the very first case challenging the underlying summary deportation policy that gave rise to Rengel's lawsuit.

On March 13, 2025, Rengel was detained by Immigration and Customs Enforcement (ICE) agents and was quickly on the first of three infamous flights to El Salvador. But litigation came quickly.

On March 15, 2025, the American Civil Liberties Union (ACLU) sued and won an immediate victory over those controversial deportation plans, which were premised on an obscure 18th century wartime authority known as the Alien Enemies Act of 1798 (AEA).

In that initial case, Boasberg worked quickly. On a Saturday, the judge issued a temporary restraining order "to maintain the status quo" that same morning and then issued a bench ruling for the Trump administration to turn two planes around containing 238 Venezuelan immigrants later that same evening.

The government openly defied Boasberg, however, and refused to interfere with the aircraft. So, the judge demanded their return.

The Trump administration, for its part, moved forward in two-pronged fashion: first, by saying it ignored the oral order because it was not repeated in a terse written order issued that same night.

Then, all but simultaneously, Department of Justice attorneys acknowledged the oral order by leapfrogging Boasberg's authority and pleading with the U.S. Court of Appeals for the District of Columbia Circuit to have the judge removed over his directive to bring back the detainees who were en route to a notorious prison in El Salvador, arguing the judge acted outside the scope of his authority.

More Law&Crime coverage: Trump attacks 'radical left' judge who halted deportations, says 'lives would be devastated' if jurists had their way against him

Two days later, the judge had his turn to express outrage.

"I memorialize it in shorthand, but you're telling me that that very clear point, you're saying that you felt you could disregard it?" Boasberg pressed Deputy Associate Attorney General Abhishek Kambli. "Because it wasn't in the written order?"

The government lawyer, for his part, repeatedly offered an iteration of an answer that suggested he was not authorized to relay any information to the court due to "national security concerns."

Next, Trump took to social media to call for Boasberg to be impeached and removed from his lifetime perch while describing the long-serving judge as a "troublemaker and agitator." Chief Justice John Roberts then issued a rare rebuke and rubbished the president's suggestion. Online, the president's allies continued to criticize the district court judge. In a motion for a stay of the temporary restraining order, the DOJ chastised Boasberg's questioning of Kambli as "purposeless and frustrating."

On March 20, 2025, the judge issued a scathing order that termed the DOJ's explanations for the government's conduct "woefully insufficient." The next day, during a hearing, Boasberg repeatedly castigated Deputy Assistant Attorney General Drew Ensign for the "intemperate and disrespectful" tone of the government's court filings, accused the administration of likely breaking the law, and promised those responsible would suffer "consequences" for violating the oral order.

On March 24, 2025, the judge declined to stay his restraining order and found the deportations that occurred in violation of that order "unlawful." Boasberg also predicted "torture likely awaits" the men sent to El Salvador and said each was "entitled to individualized hearings to determine whether the [Alien Enemies] Act applies to them at all."

Exactly one year after Boasberg's prediction, Rengel filed his lawsuit alleging torture at the hands of Salvadoran officials in CECOT. That torture, the plaintiff claims, occurred under the "constructive custody" of the United States and was only possible because of the illegal deportation flights Boasberg himself tried to stop.